Principles by Ray Dalio

The hardest thing of all to see is what is really there.

— J.A. Baker, The Peregrine

For me, there is really only one big choice to make in life: Are you willing to fight to find out what’s true?

— Ray Dalio

Ray Dalio is the founder of Bridgewater Associates (“Bridgewater”), one of the largest & most successful hedge funds of all-time (it manages $160 billion). Bridgewater has a famously unique cult(ure) of radical honesty & transparency with the goal of promoting “open-minded, idea-meritocratic, collective decision making.” If you don’t like someone, you get it out in the open, then together you figure out a way to move forward. Essentially every conversation is recorded (and every employee has access to them) so that nothing is said behind someone’s back. 40% of new hires either leave or get fired. Intense right?

Now that we know what the organization is, let’s knock out the first question.

What is a Principle? 

Principles are fundamental truths that serve as the foundations for behavior that gets you what you want out of life.

In having read Principles: Life and Work now for a third time, I realize how influential it has been and will be in my life. It’s the only book of any meaningful length I’ve read multiple times, so naturally I thought it would be appropriate for my first book review/summary. I say summary because I find his lessons so effectively communicated, it’s tough to reduce them any further.

If I had to pick one book to read this year, this would be fighting for the top spot. Your life will be more painful and better because of it. I have 143 books in my Amazon cart right now, plus some unread ones on my shelves, so in order to have a life, I have to be selective. That often means I come away from each book saying it’s one of the best I’ve ever read. With that in mind, this is one of the best I’ve ever read.

Why is this better or different than the other 25,000 business/self-help books? I’ve (regrettably) read a lot of them over the years and no other book has led to more real-world change in my life than this one. I feel like most books pass through your consciousness like advertisements; they affect you, but subtly and over time. If I had to make a blanket statement about the books in the genre, they are mostly a collection of bromides that provide no deep new understanding, and here is the real commonality: they are all positive (and life is not). Almost none encourage real pain or acknowledge how truly difficult improvement is (because that doesn’t sell books!). Think of it this way, you can read every business book and self-help book, and never manage a business, or help yourself. Said differently, there is place for them, but one can last you a long time.

If you tackle this book with an open mind, pen and paper, it will nearly force you to think and thus act differently, like the next time you hear yourself rationalizing: This is a cheat day. No, it’s Tuesday morning and eating leftover pizza at 10:00am from the night before is not going to get you to #goals.

Dalio opens the book with: Before I begin telling you what I think, I want to establish that I’m a “dumb shit” who doesn’t know much relative to what I need to know.

He probably spent a long time tailoring that sentence because of the levels to it. First level: it’s funny. Second & third levels: He is acknowledging that you should assign a “believability” weighting to him (we’ll talk about it later) and not simply take him at his word, he is relatively humble (he’s calling himself a dumb shit, which he believes, but he also implicitly believes he’s less of a dumb shit than other people because of how much work he’s put in to testing his ideas in the real world), and despite all his success, knowledge & wisdom, he is still acutely aware of how much he doesn’t know.

His sentence-by-sentence delivery is succinct (remember he’s a billionaire, not a writer), but the book is ironically 552 pages (mainly due to repetition). Any one of those pages has the potential to casually shake some readers’ intellectual foundations even between his main points. I tend to be cerebral, but this guy turns the volume knobs to an 11. This isn’t a book you read 30 minutes before you go to the bars or if you need a participation trophy. This is more for when you’ve just polished off your second 16 oz. cold brew coffee and you’re ready to be CEO of Mother Earth, or your life is going off the rails, nothing is going the way you want it to, and you need the schematics for fixing it.

The book has three parts. We’ll spend most of our time on the first half because Work Principles are simply Life Principles applied to groups.

Part 1) Where I’m Coming From (memoir)
Part 2) Life Principles (for individuals)
Part 3) Work Principles (for groups)

“When I ran into situations I hadn’t seen before, I would be painfully surprised. Studying all those painful first-time encounters, I learned that even if they hadn’t happened to me, most of them had happened to other people in other times and places, which gave me a healthy respect for history, a hunger to have a universal understanding of how reality really works, and the desire to build timeless and universal principles for dealing with it.”

Echoing Dalio’s sentiment, it seems like our attitude toward learning should be influenced by the idea that we would prefer to learn the implications of driving off a cliff by watching someone else do it than having to learn the lesson first-hand.

To give you an idea about his level of dedication & credibility, during the financial crisis in 2007, using history books and old newspapers, he and his team went day by day through the Great Depression, comparing what happened then with what was happening in the present. Further, he is admittedly terrible at rote memorization (e.g. people’s names), but he can tell you what happened economically & politically in every year since 1960.

Life Principles

Dalio defines success simply as getting what you want. I’ve been looking for a better definition for 5 years and haven’t found one yet.

“Think for yourself to decide
1) what you want
2) what is true, and
3) what you should do to achieve #1 in light of #2, and do that with humility and open-mindedness so that you consider the best thinking available to you.”

Embrace Reality and Deal With It 

Referring back to the opening quote, you can pretty much put your pencils down if you aren’t committed to finding out what’s true. It’s a waste of time to talk about individual trees if we can’t agree there is a forest. Over the past 5 years, I’ve asked several people how comfortable they are with reality, and initially I expected everyone to say that they were whether they were or not, but what I heard was a wide range of surprising honesty, with a heavier weighting of responses toward “I have a hard time with reality.” That honesty is highly valuable, because that is precisely what you need to deal with it.

The reality is, books with math in them are guaranteed to sell less copies. Dalio is a math guy though so that’s off the table, but he keeps them manageable as long as you’ve learned addition. Here are his two main formulas:

Dreams + Reality + Determination = A Successful Life

Pain + Reflection = Progress

His way of thinking could be misinterpreted as a buzz-kill, but he’s simply saying our ability to send a cell phone signal around the world or fly planes is the result of people dreaming that we could do that, while applying the existing rules of reality–the physical laws or principles that govern the natural world. When you lose your fantasy football league and have to take the SAT with high schoolers (pain), because you picked Ben Roethlisberger as your quarterback (reflection) next time you’ll pick Dak Prescott (progress).

He is ruthless and efficient in the pursuit of this.

Don’t mistake possibilities for probabilities. Anything is possible. It’s the probabilities that matter. Everything must be weighed in terms of its likelihood and prioritized.

In case you already suppose he’s a dispassionate sociopath, he says having meaningful relationships and meaningful work are the ultimate goals (I assume that’s predicated on his computer deciding you’re worth keeping around long enough for him to become your friend). Despite limiting the discussion of his relationship with his wife to slightly beyond how they met to respect her privacy, there are some surprisingly emotional personal stories. He talks about being publicly wrong about the effects of the 1982 Mexican debt crisis and his son’s battles with bipolar disorder, lightening it up with some entertaining drama–he once punched his boss in the face. He was fired for a different reason.

How to use Principles

  1. Slow down your thinking so you can note the criteria you are using to make your decision.
  2. Write the criteria down as a principle.
  3. Think about those criteria when you have an outcome to assess, and refine them before the next “one of those” comes along.

An ex-girlfriend of mine hated whenever I referred to something as a principle, and even more so when I stuck to them.

If Ray Dalio were dating my ex he would have said, “While such decisions might seem too erudite for your taste, you will make them either consciously or subliminally, and they will be very important.” I can’t replay history, but if I’d have said that, I think the relationship would have ended at “erudite”.

“People who have shared values and principles get along. People who don’t will suffer through constant misunderstandings and conflicts.”

Here’s the thing, like the guy who realized he was speaking in prose his whole life, we all have a guiding philosophy whether we know it or not. How much you tip waiters, how you handle disagreements, if you drive slowly in the left lane; these are all reflections of your principles regardless of what you call them. Although principle as a word and decision-making as a term are both abstract and mean nothing, you eventually realize that everything you do is a decision and it’s guided by a blend of conscious & subconscious thoughts and habits. Ultimately, working to improve decision-making is extremely practical.

Therefore, the most important thing is that you develop your own principles because if you accept prepackaged ones without giving them much thought, you risk living inconsistently with how you really feel, which probably won’t work out well. This is like small children espousing political beliefs, obviously regurgitating something they heard from their parents. When a kid does this, it’s cute. When an adult does, it’s dangerous.

He also emphasizes the importance of writing them down and wishes people like Steve Jobs and Leonardo da Vinci wrote theirs down. For those who find writing anything down weird, we’ll dedicate an entire post to the benefits of writing your thoughts down. For those who already write, consider adding a Decision Journal (whenever you make big decisions (new job, to move, making an investment, etc.) write down your thought process during it so you can review it later and see if you got what you wanted from your decision).

I think people allow the underlying reasons for their actions to go unexamined because it is either scary/uncomfortable to think about why we do a lot of things, and it could be viewed as unimportant if things are “just fine” the way they are. Dalio would respond to this by saying the most rewarding life comes from reaching your potential and you aren’t going to get there without reflection and discomfort. Living a comfortable life, as opposed to committing to your own painful goal machine, is neither worse nor better, if it works for you. I had a conversation about this recently. If you saw a friend you cared about sitting on a couch, doing nothing else for an entire week, and he said he was so content he couldn’t imagine anything else that could make him happier, you would be a little skeptical. That skepticism is rooted in you having experienced things that are better than sitting on the couch, and you want him to share in that joy. Without putting words into Dalio’s mouth, I think that’s his underlying belief, and he has simply taken it to the extreme in how he lives his life and operates his company.

“For all those reasons, I cannot say that having an intense life filled with accomplishments is better than having a relaxed life filled with savoring, though I can say that being strong is better than being weak, and that struggling gives one strength.”

“Encountering pains and figuring out the lessons they were trying to give me became sort of a game to me. The more I played it, the better I got at it, the less painful those situations became, and the more rewarding the process of reflecting, developing principles, and then getting rewards for using those principles became.”

Who to Trust?

You should be skeptical when you read anything, and this is no different. It reminded me of famed physicist Richard Feynman’s idea that if it disagrees with experiment, then it’s wrong. Dalio encourages everyone to poke holes in his thinking. He doesn’t care if the right answer comes from someone other than him, but he wants the right answer. I would like to be a fly on the wall at Bridgewater when he acknowledges someone has a better idea than him and watch how graceful that process is.

He even goes so far as to say knowing when not to make your own decisions is one of the most important skills you can develop. This is a balancing act between independent thinking and seeking wise counsel.

The book proposes the best standardized bullshit detector I’ve ever come across, which is applicable in all environments. “Believable parties are those who have repeatedly and successfully accomplished something–and have great explanations for how they did it.” 

It’s impossible to overstate the value of clarity and experience. If you can’t explain it, you don’t fully understand it. He makes this point several times, but my favorite is when he imagines a group getting a lesson in how to play baseball from Babe Ruth, and someone who’d never played the game kept interrupting him to debate how to swing the bat. Would it be helpful or harmful to the group’s progress to ignore their different track records? Treating all people equally is more likely to lead away from truth than toward it. But at the same time, all views should be considered in an open-minded way, though placed in the proper context of the experiences of the people expressing them. In his hypothetical scenario, he suggests having a Q&A after Babe Ruth finished explaining.

How to Argue

  1. Put our honest thoughts out on the table,
  2. Have thoughtful disagreements in which people are willing to shift their opinions as they learn, and
  3. Have agreed-upon ways of deciding (e.g., voting, having clear authorities) if disagreements remain so that we can move beyond them without resentments.

Basically, go find the smartest people you know, tell them your ideas and what you’re thinking and ask them if they disagree with you. If they do, you have an opportunity to learn. You should at least try to understand their reasoning.

This requires you to detach your ego/identity with your ideas. The way to tell you are doing this is if you remain calm when you are debating and/or wrong. Imagine if all debates (e.g. presidential, media, personal) required each party to stand in separate soundproof booths with microphones and they cut off at a certain volume threshold so nothing could be heard until the person lowered their voice to an appropriate volume.

Peter Thiel’s favorite interview question is: What is something that is true that almost nobody agrees with you on? We won’t spend much time on Thiel today, but this section of the book reminded me of my answer to his question: Disagreements are good, if you are open-minded. I argue almost exclusively with people I like. Why? Because I care about their thoughts and want them to challenge mine. Arguing with people in the confrontational sense is a fool’s errand. Arguing with people in the truth-seeking sense is beautiful. The distinction is adopting an attitude of cooperation towards the topic as opposed to demonstrating superiority. Conversation is plainly the real word, but I use argue to acknowledge the reality that it’s impossible to have the same ideas as someone on everything. Handling that in a real way instead of sweeping it under the rug in superficial agreement is the basis for a genuine relationship. Ego detachment opens the door for calmness and the calmness leads to clear thinking and that leads to all sorts of good things.


Dalio’s mindset towards work is: we have the best chance of succeeding if the best idea wins every time. Everything above applies to this goal. If you can do something, that’s great. If you can’t, learn or find someone who can.

Creating this type of company or culture may be unobtainable or unrealistic for many. The prerequisite ingredients alone are rare, much less the execution & maintenance.

If you’ve worked at a big corporation, you may be laughing at the prospect of managers even acknowledging reality within their department, much less them actively looking for ideas better than theirs. It’s equally unusual to find employees openly professing their weaknesses in an effort to get the best possible idea out there, especially if that “best idea” means someone else gets promoted over them or that they are unnecessary to the company. It sounds good on paper, but even if you get past the fact that most people understandably care more about their own well-being than a company’s, you still have big obstacles.

It says a lot about the state of affairs when it’s controversial to be transparent and honest.

“But while almost all of us quickly agreed on the principles intellectually, many still struggled to convert what they had agreed to intellectually into effective action. This was because their habits and emotional barriers remained stronger than their reasoning.”

It’s all too easy to see how difficult Dalio’s concepts are to implement, which is why I think it’s more practical to factor them in while developing your personal principles. In a work context, you need to be the founder/CEO to have any real chance at comprehensively incorporating them. Or go work for Bridgewater.

Here’s a summary of the work tools/apps Bridgewater uses (complementing the book, Dalio is going to release versions for the public):

  • Baseball Cards: Each employee has a card that lists their stats. Spoiler alert, this wasn’t initially well-received.
  • Issue Log: Primary tool for recording mistakes and learning from them
  • Dot Collector: An app used in meetings that allows people to express their thoughts and see others’ in real time. Participants continuously record their assessments of each other by giving them “dots,” positive or negative, on any number of several dozen attirbuts.
  • Pain Button: An app allowing you to record the emotions they’re feeling in real-time, then come back at a later time to reflect on them
  • Dispute Resolver: App that asks a series of questions used to guide people through the resolution process
  • Daily Update Tool: Brief email of what they did that day, issues pertaining to them, and their reflections
  • Contract Tool: App that lets people make and monitor their commitments to each other.

I admire his ability to walk the walk here. Admittedly, I’ve never created, nor particularly desired, this level of accountability for anything. It’s an idea carried to its logical extreme, in the same way that Michael Jordan carried the idea of being good at basketball to a logical extreme.

Oh by the way, he literally takes all of these principles and builds them into algorithms so that computers are making the investment decisions and he’d like to get them making hiring & firing decisions, too. The skeptic in me thinks he is going to use the data from the apps to find top talent and/or use it as a database for Bridgewater.

Final Thoughts

Dalio attributes much of his success to Transcendental Meditation, which he has practiced for 30+ years. Nothing of any substance he advocates for is possible without making time for reflection.

Even though the book is largely about his life and principles, one of my favorite passages is his timely perspective on geopolitics.

“Most people who haven’t had direct contact with the leadership of their own and other countries form their views based on what they learn in the media, and become quite naive and inappropriately opinionated as a result. That’s because dramatic stories and gossip draw more readers and viewers than does clinical objectivity…As a result, most people who see the world through the lens of the media tend to look for who is good and who is evil rather than what the vested interests and relative powers are and how they are being played out.”  

I feel like that quote is going to hang around for a while.

Throughout his life, he found himself at big moments wanting two seemingly incompatible things. As someone who loves nothing more than having his cake and eating it too, I was particularly curious how he goes about such situations: slowly and creatively. This could be considered useless advice, but I’ve seen the power of slow progression. “Slowly” is the answer for a lot of things, including the related topic of circularity (chicken & egg) problems which have been on my mind the past year or so. Since management strategy & circularity is right in Venkatesh Rao’s wheelhouse, I hope he reads the book and provides his own review.

Most visitors to this thought sanctuary already know there’s no such thing as a “life secret”. There is the connecting & executing of ideas that are readily available to those seeking them. That’s the beauty of his advice, if you figure out what the right decision is and you have the courage to make it, your life will be better. It’s all about the execution.

Know that the most constant struggle is between feeling and thinking.

Ultimately, this is a book about tough love. I hope you struggle well.

See Also:
Is Bridgewater a Fraud? (unlikely, but always consider the other side right?)
Ray Dalio’s Ted Talk

Designing Your Life


verb  de·sign \di-ˈzīn\

1: to create, fashion, execute, or construct according to plan
2: to plan and fashion artistically or skillfully
3: to intend for a definite purpose

There is only one success in life — to be able to spend your life in your own way. 

— Christopher Morley 

The chains of habit are too light to be felt until they are too strong to be broken.

— Warren Buffett

When you were in elementary school and your teacher asked you to draw a picture of your life on a blank sheet of paper, your Crayola stick figures probably were not on the phone with AT&T asking them in restrained deep breaths to explain how your phone bill is different every single month. Nor were they likely choosing between different door knobs at The Home Depot on a nice little Saturday. 

I was lucky if I was well-behaved enough to even participate in the drawing activity, so now that we are all adults let’s revisit the idea. One problem with asking young people to draft their futures is they have no idea what possibilities are available. This is the basis for travel, knowledge, and experience. How can you know what you want if you don’t know it exists? If you lived in the US before 1980, there is a good chance you had never eaten sushi. Take my eyes but not the sushi.

The rapid pace of technological developments makes predicting our opportunities even harder. Take virtual reality. Although the foundations were set long ago, the impending widespread use is something relatively few people outside Silicon Valley were aware of five or ten years ago. Whether it is sushi or VR, the more familiar we make ourselves with the physical, social, and cultural aspects of the world, the more capable we are to label our wants, and thus get them.

When I look around I see that some people have better lives than others (it is amazing how reluctant people are to explicitly acknowledge this and will inevitably be a topic we explore in-depth later). Of course each person’s genetics, environment, & relative positioning within that environment are critical. If your dad is Shaq, you are going to be tall. If you were born in the US, you have access to air conditioning and medicine. If your mom is the CEO of the corporation you want to work for, guess who is getting that summer internship.

Having said that, there is room for decision making in determining outcomes. The problem is, most people shape their lives without knowing it through the decisions they make every day. I cannot seem to shake this theme. Even people that seem like they don’t have choices do. Nelson Mandela spent 27 years in prison and he still found time to run a country, abolish apartheid, and get Morgan Freeman to play him in a movie.

You make thousands of decisions every day. How many times to hit the snooze button, who to email, call and visit, what websites you go to, number of cartons of Halo Top to eat, and so on. If we have control over these micro-decisions, do they add up over time to something more meaningful, and can we steer them in a direction that leads to only having the people, things and experiences in our life that we want? If so, would it make sense to consciously figure out what we want ahead of time? This is what I mean by designing your life.

It is like a bucket list, but for while you are living normally, not just before you die.

Like any idea, this can be carried to extremes. Our actions are rarely insulated to ourselves, so don’t mistake this to be suggesting that you surround yourself with people who enable you to live in your own unchecked fantasy (you know someone who does this and it is not a good look). Having said that, the people you have in your life profoundly impact the quality of it and I have found that I generally want to avoid the type who stand under waterfalls and complain about being wet. We’ll find the right balance.

The only reason this idea justifies an essay is because of the second & third-order effects. It is quite obvious that everyone wants what they like and they generally make decisions they think will get them those things. However, it gets a little nuanced when 1) we do not know ourselves and therefore our true wants and/or 2) choosing something we want today means we will be unable to have 10 things we want in five years. Let’s make sure we are on the same page with order effects. Take exercising. First-order effects are sweating, exhaustion, and some level of euphoria. A second-order effect would be better posture, or not panting after walking up a flight of stairs. A third-order effect would be lower lifetime healthcare costs due to improved health which frees up time & cash for you to do and buy other things.

People usually start doing something for first-order reasons, but down the road through an accumulation of the small decisions we mentioned earlier, end up somewhere else due to the second- or third-order effects – sometimes undesirable. The opposite is also possible. In our future life drawing, we may have been incapable of imagining a future job as an electrical engineer or sommelier (sign me up), but through continuous iterations of deciding what we like as we go through more experiences, we end up somewhere with a previously unimaginable & desirable result. I suppose if you stand behind every decision and action you ever make then who cares where you end up?

Here is a hypothetical, but useful, example of things getting away from us. Suppose a guy says, “I want a big house in a good school district because my wife wants one, that would be great for my family, and that is what people do.” Well, pretend it is slightly outside the budget, the mortgage payment stresses him out on a daily basis, and he’s at work too long trying to pay for it. Therefore, he never spends time with his wife and kids. Each time something breaks, his face gets a shade more red. Multiply this daily routine by a few years. Gets divorced, sells the house, and the kids become Tennessee Volunteers fans (Go Dawgs). Complete misery.

As a reminder, I have nothing against houses. I use them as examples because they are ubiquitously relatable to most Americans. In fact, your housing and where you live are essential components of designing your life. Winston Churchill nailed the idea mid-cigar when he blew out a contemplative cloud of smoke and said, “First we shape our buildings and then they shape us.”

Two central premises to this are the importance of time and agency over your life. Those who do not feel the clock of their life ticking or often feel like victims of circumstances will not find this concept compelling.

There are two general approaches to designing your life:
1) being selective about each addition to it (harder on the front-end — try resisting Netflix or french fries)
2) experience as much as possible and cutting out/replacing the ones you do not want (harder on the back-end — try deleting Facebook, permanently ending a toxic relationship, or even worse, trying to reverse irreversible outcomes). In design, there is an idea that when you are trying to make something beautiful (for instance a bedroom), first remove everything that is ugly. This is a useful heuristic, especially for older people who are unsatisfied, but do not know where to start. Ask: What do I dislike the most about my life?

Regarding #1, Warren Buffett says, “The difference between successful people and very successful people is that very successful people say no to almost everything.” Don’t go watch Yes Man right after reading this or you’ll be stressed out for the rest of the day. The quote has layers of meaning to it, but the relevant point is there are so many things competing for your attention, if you are always saying yes you are spreading yourself too thin and you are by definition not focused. I practice what I preach, but this one is difficult for me.

I will use an easy example in my own life for #2. When I first started working, I wanted to be Frugal Fred and save money, so I ironed my own shirts. I hate ironing shirts. As one of the world’s worst/most distracted ironers, I can probably iron 5 shirts an hour because I watch stand-up comedy on Netflix while I do it. There is pathetic and then there is 5-shirts-an-hour pathetic. I decided to deploy what economists call comparative advantage and let the professionals do it for $1.25/shirt. If you do not already do this, you should quantify how much your time is worth (working) per hour and what a reasonable threshold is to outsource chores and routine tasks, because once you are putting significant amounts of energy into your craft/occupation, saving $6.25 when you could be recharging is simply not worth the energy. Mathew McConaughey’s threshold is higher because in an hour he can make $100,000 shooting a Lincoln commercial. No idea if that number is right, but you get the idea. Star Cleaners is better off pressing my shirts and I am better off not having interruptions so I can focus on the things I want to focus on. What optimists call a win-win.

Once you pick your approach, it sounds alluringly simple: Imagine your life exactly as you want it. Then make decisions that get you closer to that. However, readers will notice that constraints, trade-offs, and discipline have either been implicit or explicit in every post so far. There will be blood.

It can be as simple as if you hate traffic, get a place close to work. If you hate work, spend time outside of work deserving the job you want. If you want to save money, do not spend it all on rent, car payments, and going out. But we want it all. The place next to the office may cost more, your social life may be more important than your career, and so on.

This is where the decision-making part comes in and you figure out what you really want. It is better to do this deliberately. Venkatesh Rao over at Ribbonfarm would caution against “getting trapped in imitative life scripts that may not work for you.” This is similar advice to “You do you” (which could be valid if it was not mostly given at terrible times). In other words, if you try to copy the design of someone else’s life, it will likely disappoint.

We need feedback to determine the quality of our decisions. The feedback from our choices is often received fastest in our physical appearance and mood. Like our life, we can shape our body, getting closer to what we ideally want it to look and feel like. We control this with inputs, rest, exercise, skincare, et cetera. A medium- to long-term approach in these categories gets rewarded. Once you begin to see the cause-effect relationship in such a direct way, it gives you confidence to trust the process in planning longer-term, more abstract goals where the feedback is often delayed and sometimes invisible. For instance, if you want a strong vocabulary (abstract goal), the most effective way to achieve this is by reading the work of great writers. If you read one book, you will not notice any effects. If you read 100, you will.

In the way I imagine it, designing your life entails taking steps to make each phase or season of your life better (abstract goal) than the one before it, however you define that. I am sure we can agree that increasing degrees of freedom is better. There is a paradox here. When you were a kid you did not have a driver’s license and now that you are an adult you do not have to sit in a classroom for 7-8 straight hours like you did in school, so at least spatially, you have much more freedom. However, most adults would laugh at the idea that they have more freedom now. This is because of the way they have designed their life and the responsibilities their choices and circumstances necessitate.

For adults, freedom is almost synonymous with money. Although financially, it is easier than ever to design your life, this convenience can get slippery. One day you buy something online. Next thing you know you have Amazon packages magically appearing on your doorstep every day. Good for Amazon, bad for your credit card statement.

As you can see from the few examples here, each seemingly compartmentalized part of our lives spills over into another, adding complexity, and there are infinite directions to take this idea. Your life is your canvas.

Occasionally, someone will say, “Not everything has to be so planned out JOSH, just go with the flow,” or something similar. This person either innocently misunderstands what I am saying or more likely, has just realized how doing some of these things could have prevented pain. It is crucial to be clear on these two possibilities. One, spontaneity is great. The best day of your life is not the day you plan to be the best day of your life. The entire goal of planning is to save time and give you flexibility, not cause stress. Relaxing is not wasted time. It could be argued that the goal of human activity is leisure time. In contrast, wasting time is doing something without a benefit. If you value a ton of time spent on the couch watching football and you can support that lifestyle, structure your life such that you can spend heaps of time on the couch watching football. For the second, mistakes happen. Some are fixable, some unfixable, some in our control, many out of our control.

We are simply aiming for better-than-random conditions for ourselves. 

See also:
The Design of Everyday Things by Don Norman

Algorithms to Live By: The Computer Science of Human Decisions
by Brian Christian & Tom Griffiths

Stumbling on Happiness by Daniel Gilbert

Where’s the bag?

Wisdom crieth aloud in the streets.

Proverbs 1:20

Floyd Mayweather, Jr. carries around a bag that has $1 million cash in it. He often has an entourage with him, and if he’s not carrying it, he frequently asks to no one in particular, “Where’s the bag?”

There’s a case to be made that this is dumb, and other reported & rumored things Floyd does are loathsome. But, I look for good ideas wherever I can find them and it reminded me of a piece of advice Warren Buffet received and reprinted in his 1970 Letter to Shareholders.

Dear Fred & Catherine [Buffett’s uncle & aunt]:

Over a period of a good many years I have known a great many people who at some time or another have suffered in various ways simply because they did not have ready cash. I have known people who have had to sacrifice some of their holdings in order to have money that was necessary at that time.

For a good many years your grandfather kept a certain amount of money where he could put his hands on it in very short notice.

For a number of years I have made it a point to keep a reserve, should some occasion come up where I would need money quickly, without disturbing the money that I have in my business. There have been a couple occasions when I found it very convenient to go to this fund.

Thus, I feel that everyone should have a reserve. I hope it never happens to you, but the chances are that some day you will need money, and need it badly, and with this thought in view, I started a fund by placing $200.00 in an envelope, with your name on it, when you were married. Each year I added something to it, until there is now $1000.00 in the fund.

Ten years have elapsed since you were married, and this fund is now completed.

It is my wish that you place this envelope in your safety deposit box, and keep it for the purpose that it was created for. Should the time come when you need part, I would suggest that you use as little as possible, and replace it as soon as possible.

You might feel that this should be invested and bring you an income. Forget it — the mental satisfaction of having $1000.00 laid away where you can put your hands on it, is worth more than what interest it might bring, especially if you have the investment in something that you could not realize on quickly.

If in after years you feel this has been a good idea, you might repeat it with your own children.

For your information, I might mention that there has never been a Buffett who ever left a very large estate, but there has never been one that did not leave something. They never spent all they made, but always saved part of what they made, and it has all worked out pretty well.

This letter is being written at the expiration of ten years after you were married.


The letter was written in 1940 and Buffett found it in 1970 (with the $1,000 still there haha). To modernize the advice, using an inflation calculator I found on Google, $1,000 in 1940 is equivalent to $17,623 in July 2017. Buffett’s company, Berkshire Hathaway, takes it a step further than Floyd, and keeps $20 billion. We can tailor our number to our individual circumstances. I like the advice (including the safety deposit box) precisely because it feels unnecessary and inconvenient.

Can you imagine one day waking up and getting this email from your bank?

“Sorry, we got hacked. We think you had $x in your account. You’re prolly not getting it back. Hopefully the FDIC has you covered. Maybe check out Bitcoin. If the power hasn’t gone out. Peace & Blessings.”

“Where’s the bag?”
— You, next year


Jiro Dreams of Sushi is the best movie about Steve Jobs ever made. 

— Chris Dixon

Take a moment to consider the following: What is quality? When you drive by Wendy’s and see “Quality is Our Recipe” on the sign you know they’re full of shit, but why? This is the paradox: we all have an intuitive sense of what “quality” is, but it’s difficult to define, and if we can’t define what it is, how can we pursue it?

When my best friend told me Robert Pirsig’s book, Zen & the Art of Motorcycle Maintenance: An Inquiry into Values (“ZAMM”), tries to answer that question, my eyes stretched wide open because the theme had been on my mind for a while and I was intrigued that someone had put a book-length effort into thinking about it 15 years before I was born.

The book title initially confused me because it turns out it’s not really about Zen or motorcycle maintenance — it makes more sense to think of Zen as living in the moment and motorcycle maintenance as rational thought. The narrator explores how we can combine artistic free-thinking creativity and the reason & logic of technology through a 17-day motorcycle trip from Minnesota to Northern California with his son. The thought is to be so engaged in what you are doing that you become one with it. For example, it is hard to imagine Jimi Hendrix without a guitar. Pirsig’s guitar is a motorcycle and the metaphor for his story.

Since then, I have read the book and later stumbled on Paul Graham’s essay Taste for Makers, in which he tries to answer the question: “how do you make good stuff?” Like when you are buying a new car, you actively notice everything about cars, I couldn’t help being on the lookout for quality.

Quality materials last. Quality people are trustworthy. Quality decisions rely on logic, courage, and intelligence. Regardless of what we are talking about, there is an insatiable appetite for quality.

I thought about Jiro Dreams of Sushi, a phenomenal documentary available on Netflix about one of the world’s greatest sushi chefs. The parallels were hard to ignore. The opening scene of the film shows Jiro writing in Japanese and he says, “Taste is tough to explain, isn’t it?” The opening quote by Chris Dixon succinctly draws the comparison between Steve Jobs and Jiro in that they obviously have drastically different products (personal electronics & sushi), but the level of passion they have invested in perfecting them is nearly identical.

Pirsig, Graham, Jiro, and Jobs. A philosopher, venture capitalist, chef, and a technologist. They are all pursuing the same thing, just using different means and different words. Graham’s, being a 16-page essay, and Jiro, a movie, are more approachable, while ZAMM is a philosophical text (easier to read than most) thinly disguised as a novel. The underlying idea here deeply resonates with me and I think that a fulfilling life is dependent on the pursuit of quality, taste, or whatever we call it. It’s funny, I used to think I wanted to be happy. But, what I realized is that satisfaction is actually superior to happiness because you cannot pursue happiness directly. Happiness is what’s left after you have done something else. I would imagine that a NY firefighter on 9/11 would not describe himself as happy, but would feel fulfilled and satisfied by saving lives. There is a lot here, so we will probably expand on certain ideas in the future. For now, let’s figure out how quality fits into our lives and how it can enhance them.

For better or worse, it is nearly impossible to talk about quality without getting into epistemology (theory of knowledge) because when you say “good” it is kind of in-between subjective and objective. Your 6-year-old son may be good for his recreational basketball league, but Lebron James is good period.

I think what turns people off from philosophy are two related things:

1) it rarely proves anything (which is ironically interesting)
2) after a few minutes the conversation often drowns in a pool of abstraction and loses application to your day-to-day life. Perhaps we can summarize the sentiment with, “Whether the chair exists or not, we still have to go to work.”

Pirsig tries to maintain the casual reader’s interest by using Chautauquas: old-time series of popular talks intended to edify and entertain, improve the mind and bring culture and enlightenment to the ears and thoughts of the hearer (cough, the entire goal of this blog, cough).

Since Pirsig & Graham did the heavy lifting already, their ideas and quotes are going to serve as the basis for the post and I’m going to chime in with some thoughts along the way. Graham’s writing style is one of the best in the world. He tactfully acknowledges why a politically correct sentiment exists and then gets to the core of an interesting idea in plain language.

Saying that taste is just personal preference is a good way to prevent disputes. The trouble is, it’s not true. You feel this when you start to design things.

Whatever job people do, they naturally want to do better. Football players like to win games. CEOs like to increase earnings. It’s a matter of pride, and a real pleasure, to get better at your job. But if your job is to design things, and there is no such thing as beauty, then there is no way to get better at your job. If taste is just personal preference, then everyone’s is already perfect: you like whatever you like, and that’s it.

As in any job, as you continue to design things, you’ll get better at it. Your tastes will change. And, like anyone who gets better at their job, you’ll know you’re getting better. If so, your old tastes were not merely different, but worse. Poof goes the axiom that taste can’t be wrong.

— Paul Graham, Taste for Makers

His delivery is light, but the challenge is real: Be better than you were. He then goes on to describe the principles behind good design.

This theme of self-improvement is natural to us, but it feels more inspiring when coming from people at the top of their field.

I do the same thing over and over, improving bit by bit. There is always a yearning to achieve more. I’ll continue to climb, trying to reach the top, but no one knows where the top is.

— Jiro Ono

My favorite scene in Jiro is an interview with one of his tuna vendors, Hiroki Fujita, at the fish market. Fujita says, “I either buy my first choice, or I buy nothing. If ten tuna are for sale, only one can be the best. I buy that one.” In-between the lines is the implication that you need to know tuna well enough to know the difference. To know what you want, to know it when you see it, and to pursue it exclusively. Do you know what you want, would you recognize it if you saw it, and would you say no to almost everything else to get it?

(From here, unless otherwise noted, block quotes are from ZAMM.)

P. 8 “What’s new?” is an interesting and broadening eternal question, but one which, if pursued exclusively, results only in an endless parade of trivia and fashion, the silt of tomorrow. I would like, instead, to be concerned with the question “What is best?,” a question which cuts deeply rather than broadly, a question whose answers tend to move the silt downstream.

What is best is tricky. We all want the best tuna. Realistically, we should qualify it and say: What is best, given a set of constraints? If I required the best every time I had a late-night pizza craving, then I’d need to go to Italy (or Chicago), on a G6, with Chesley “Sully” Sullenberger flying it.

Having said that, “best” does not necessarily mean most popular or most expensive. Twilight sold about 120 million copies and most Pulitzer Prize winning books sell under 1.5 million copies. You can have a quality toothbrush that you spent $4 on and a lemon car that costs $50,000. Now, often the best becomes both popular and expensive because word gets out and if more people want it, the product or service will likely cost more.

Regarding material items, functionality and durability are important elements of quality. If you wear a $1,000 jacket 1,000 times ($1 per use), I’d argue that is less expensive than a $500 jacket that wears out after wearing it 10 times ($50 per use). Filson and Patagonia are good examples of this concept, which reminds me of an old Russian proverb: We’re not rich enough to buy cheap things.

P. 27-28 We were all spectators. And it occurred to me there is no manual that deals with the real business of motorcycle maintenance, the most important aspect of all. Caring about what you are doing is considered either unimportant or taken for granted.

Whether it is a friendship, a garden, or an Excel spreadsheet, caring about what you are doing is arguably the most important attribute you can have because of how much it encapsulates. With sushi, you could say, “It’s just a piece of fish on top of rice.” That dismissive line of thought is deceptive though. Although the statement is true on the surface, watch the movie and see if you think there is a difference in the level of care between the fish on rice on a conveyor belt compared to the fish on rice at Jiro’s restaurant. Caring is like authenticity, there are no shortcuts and tends to require a significant time investment.

P. 28 I don’t want to hurry it. That itself is a poisonous twentieth century attitude. When you want to hurry something, that means you no longer care about it and want to get on to other things.

Hurrying, and the related concept of being busy, is not just a poisonous twentieth century attitude…it survived Y2K and came right into the 21st. You rarely catch yourself rushing the important things and you always make time for the ones you care about the most. At Jiro’s restaurant, “after about ten years, they let you cook the eggs.”

Pirsig was a creative & technical writing professor for a brief period of time. If you read the book, you get the sense that although he had the best intentions and thoughts as a father and professor, he probably didn’t come across as good at either at the time.

P. 176 And he became convinced that all the writers the students were supposed to mimic wrote without rules, putting down whatever sounded right, then going back to see if it still sounded right and changing it if it didn’t.

Rules are alluring because they provide a step-by-step guide to get what we want and processes are usually helpful. However, I cannot think of a single person who I would consider great who simply followed a set of rules. Instead they worked on their craft until it felt right. Going with your gut is a terrible strategy for accounting, but critical for design and creating. This gut feeling comes from getting the reps in. One of Jiro’s apprentices said, “He gives me advice. But, there is much you can’t learn from words. I have to keep practicing.”

P. 209 What he meant by Quality was obvious. They obviously knew what it was too, and so they lost interest in listening. Their question now was “All right, we know what Quality is. How do we get it?”

He singled out aspects of Quality such as unity, vividness, authority, economy, sensitivity, clarity, emphasis, flow, suspense, brilliance, precision, proportion, depth and so on; kept each of these as poorly defined as Quality itself, but demonstrated them by the same class reading techniques.

It doesn’t make a bit of difference how you do it! Just so it’s good.

It impresses me when someone says something so eloquently I think to myself “Oh that is exactly how I would have said it,” when in fact I couldn’t say it anywhere close to as well as them. This ties into his “taken for granted” comment above. Dismissing the concept as obvious is precisely why so many people fail at it. Graham goes a bit further in his characteristics, giving us more concrete examples and hints at how we can go about achieving them.

Everything we have talked about so far has been inwardly focused, so we have to be honest with our motives. Graham says the greatest masters go on to achieve a kind of selflessness.

P. 212 Any effort that has self-glorification as its final endpoint is bound to end in disaster. When you try to climb a mountain to prove how big you are, you almost never make it. And even if you do it’s a hollow victory. In order to sustain the victory you have to prove yourself again and again in some other way, and again and again and again, driven forever to fill a false image, haunted by the fear that the image is not true and someone will find out. That’s never the way.

(Insert flushed face emoji)

P. 218 And interestingly [without Quality], comedy would vanish too. No one would understand the jokes, since the difference between humor and no humor is pure Quality.

I am going to get this quote tattooed in Chinese on my lower back.

P. 310 Of the value traps, the most widespread and pernicious is value rigidity. This is an inability to revalue what one sees because of commitment to previous values. In motorcycle maintenance, you must rediscover what you do as you go. Rigid values makes this impossible.

Robert Pirsig was talking about Confirmation Bias in 1974 long before it was trendy. We talked about this in an entire post here. Graham says Good design is redesign and “it takes confidence to throw work away.”

Suppose we have gotten past Confirmation Bias, we are willing to overturn closely held ideas and previous values, and everything else that goes along with Pirsig’s rediscovery process. No matter how adaptable we may be, somewhere along our journey we will reach a point where there is no readily available solution and there is no good outcome. Pirsig calls this being stuck. I loved this part of the book because we are so often tempted to rationalize away bad circumstances. Sure we can learn from failure, no it is not the end of the world, but sometimes things are objectively bad at that particular point in time–no silver linings. He offers some guidance for this situation:

P. 311 …well…just stare at the machine. There’s nothing wrong with that. Just live with it for a while.

Of the people I have met and know, several are highly uncomfortable being mentally still. It is important to distinguish being still from being lazy or boring. I believe the reason for this is that in the absence of distractions, people are confronted with the real issues or questions in their life that need to be addressed. This can be scary. However, I think part of the rise in popularity of yoga and meditation is because putting the body to work on a prosaic task (yoga, chopping wood, cleaning) that requires minimal effort allows the rest of the mind to reflect. We all need this.

P. 325 The real cycle you’re working on is a cycle called yourself. The machine that appears to be “out there” and the person that appears to be “in here” are not two separate things. They grow toward Quality or fall away from Quality together.

P. 164 The ultimate test is always your own serenity. If you don’t have this when you
start and maintain it while you’re working you’re likely to build your personal problems right into the machine itself.

If you’ve ever gotten mad at an inanimate object, you understand this at least to some degree already. Everything you work on is a reflection of yourself. It took me ~25 years to figure this out because I also believe that which isn’t worth doing, isn’t worth doing well. Figuring out what to do is often at least as hard as the actual doing.

P. 386 It is an immortal dialogue, strange and puzzling at first, but then hitting you harder and harder, like truth itself.

When you find out there is something wrong with the cycle called yourself, it tends to make us angry. If it makes us angry enough, we will pretend there is nothing wrong with the cycle and you can imagine how that impacts where we are going.

This is something to think about in doses. Pirsig thought about this stuff so much it drove him insane.

By this point, the content of this excerpt from a Playboy interview of Steve Jobs in 1985 will sound familiar:

Playboy: Does it take insane people to make insanely great things?

Steve Jobs: Actually, making an insanely great product has a lot to do with the process of making the product, how you learn things and adopt new ideas and throw out old ideas. But, yeah, the people who made Mac are sort of on the edge.

Playboy: What’s the difference between the people who have insanely great ideas and the people who pull off those insanely great ideas?

Jobs: Let me compare it with IBM. How come the Mac group produced Mac and the people at IBM produced the PCjr? We think the Mac will sell zillions, but we didn’t build Mac for anybody else. We built it for ourselves. We were the group of people who were going to judge whether it was great or not. We weren’t going to go out and do market research. We just wanted to build the best thing we could build. When you’re a carpenter making a beautiful chest of drawers, you’re not going to use a piece of plywood on the back, even though it faces the wall and nobody will ever see it. You’ll know it’s there, so you’re going to use a beautiful piece of wood on the back. For you to sleep well at night, the aesthetic, the quality, has to be carried all the way through.

It has been several years since I read Steve Jobs’ biography, but it sounds like he read ZAMM.

I wonder how Jiro would respond to the same question about insane people and great products? Jiro and his employees memorize the seating chart of the guests of the restaurant by gender before they arrive, so that the women are served slightly smaller portions than the men in order to keep a harmonic pace to the meal, ensuring everyone finishes at the same time.

Most people like interviews and profiles of successful people because they potentially offer insights into the traits that caused their success. So, let’s say there is a spectrum of personality traits and on one end is living-in-the-moment and at the opposite end is rational analysis we alluded to above. It is likely that we lean towards one end or the other and have a tendency to at least subconsciously think people who are more of the other type just do not get it, which can’t be the case. If we can gravitate towards the center over time, I think we will have a higher quality of life regardless of whether we maintain motorcycles, create the next iPhone, or make the best sushi.

A focus on quality is an end in itself, but it has additional second-order benefits, too. It will filter your true wants. If the quality of something is not that important to you, you probably do not need much of it in your life. This reduces the number of things you want, which almost literally means you will be happier.

Go for quality.

See also:
Zen and the Art of Motorcycle Maintenance
Paul Graham’s Taste for Makers essay
Playboy Interview with Steve Jobs (1985)
Let My People Go Surfing by Yvon Chouinard (founder of Patagonia)
Satisfaction by Gregory Berns
Man on Wire (documentary)


50+ Shades of Gray: Opinions, Mental Models, & Probability


I never allow myself to have an opinion on anything that I don’t know the other side’s argument better than they do.

— Charlie Munger, Vice Chairman of Berkshire Hathaway


Since no one really talked about this past election, and politics are rarely an emotive topic, let’s use that to introduce the subject of today’s conversation (trust me, we won’t stay long). Whether you voted for the Mad Mango, The Criminal, or Francis Underwood, I am indifferent. What is much more interesting is the step before: our decision making framework, and how it affects what we do and choose. Before the election, across different states, countries, people, and age groups, I heard similar sentiments and shockingly similar sentences used to describe why people were voting for a particular person. Some people talked about rationally-considered pros and cons of the situation. Many more had an opinion on topics that not only appeared to be insignificant in relation to the country’s real issues (if someone starts talking about bathrooms, I start wondering what they are distracting me from thinking about) or seemed to ignore a candidate’s ability to execute on promises (classic), but those opinions seemed to be immovable the moment they left the lungs. The rhetoric & villains were getting all too predictable. The first thing we must acknowledge is that this is a complicated system we are in and it absolutely requires latitude in our thought. An inflexible thinker in life is comparable to an inflexible gymnast in the Olympics.

If stubbornness were wine, ignorance would be the grapes. Have you noticed you cannot reason someone out of something they did not reason themselves into? Given that each of us is more likely to be persuaded by the ideas we discover on our own than from other people, if there is one area where we can hold our proverbial horses, it is in the initial formation of our opinions and ideas. Let’s become comfortable with saying “I don’t know” for a while. Why? First, Munger’s quote above; it should be on the ticker of every news station and inside every fortune cookie (in bed). Second, with seven billion people on the planet, there are simply too many things happening to have an opinion on each of them. Third, the easy problems have been solved, leaving us with the harder ones with less clear answers. Fourth, once we form an opinion, we hold onto it and the only way we let go is if someone pries it from our dead, lifeless fingers. Finally, I think the truth is often difficult and that any improvement in our appreciation for nuance makes our society better. I am not talking about a better society in the abstract Let’s Love Everyone sense. I am suggesting that we have a responsibility to spend adequate time and energy developing our ideas and to effectively commit to lifelong learning, because my guess is that the average reader here has a long life to live, and we are not going to get very far based on what we already know. If we do this we will each receive a (yuge) personal benefit, sure. But it will generally be a net positive for everyone else, too. We will reduce the number of people who confidently answer questions about which they don’t have any real knowledge.

When I talk about this idea, occasionally I’ll hear the fingernails on the chalkboard: “Everyone is entitled to their opinion.” No. No, they are not. If this is a belief of yours, spend 10 minutes on Facebook and get back to me. Let’s say someone asks you and me what the marginal tax rates should be and you have spent 30 years trying to figure this out and this is the first time I have thought about it. Our opinions are not equal and I haven’t earned the right to say much on the topic. “Well that is just my opinion” requires no further justification when we’re talking about the best burger in Dallas (Maple & Motor), but more serious things require more homework.

As more time is spent on any one thought, serious thinkers start bumping into paradoxes. Have you tried getting a black and white answer on a topic from an expert? It is harder than convincing your friend not to text their ex. Easy example: Is coffee good for you? The answer is unexciting: it depends (on several things, including the definition of good). Wars don’t get started and magazines don’t get sold over “it depends” though. Of course, many things have objective answers. DNA carries the genetic information of a cell. A balance sheet must balance. La La Land Moonlight won the Oscar for Best Picture. The key, and potentially uncomfortable, realization we have to face is: Many areas outside of the hard sciences do not have answers and facts in the traditional sense, but instead entail a series of options along a continuum, with trade-offs (shades of gray). The more objective answers we accumulate, the more equipped we are to assess those trade-offs.

There are two main risks to walking down this path of deliberation and open-mindedness:
1) We eventually have to do something. We can’t just keep all of this in our heads indefinitely, we want to use it. This one is easier because we’ll often be told we need to do something faster than we do. You don’t just get in the car and drive to Chick-Fil-A. You avoid a lot of pain and agony if you first think about whether it is Sunday or not.
2) Many people are trying to fool you. This is the bigger one – If we are too open-minded we will end up in a cult with a lot of product warranties, organic pet rocks, and free cruises. So we should be skeptical of experts and marketing (future post), but we also must be mindful that if it is an area largely unfamiliar to us, we have some old-fashioned work to do. I wish there was another way around this.

You may be thinking: he wasted 900 words (and we are not done yet) to suggest we should know what we are talking about and consider the other side of an argument. There is more to it, and the thing that makes this polite suggestion effectively worthless is Confirmation Bias. We seek out information that (wait for it) confirms what we already believe. You don’t see protesters with signs that read: “EXCELLENT POINT! I HADN’T THOUGHT ABOUT IT THAT WAY BEFORE!!!!!” Those people have pounded the same ideas into their head for so long and only surrounded themselves with people like them that they have ruined their mind. I am not in love with too many ideologies, but I can kind of empathize: if avocado availability were threatened, I would be doing more than protesting.

The better, yet emphatically less popular, strategy is to seek out information that disconfirms what we believe. Now why in the hell would we do that? Because we want to be rational. How else are we going to figure out the truth if we are only exposed to a partial amount of information? This is a tall order considering new information is usually rejected due to an emotional or financial conflict, the tendency is to hold onto a belief long after it is proven wrong, and the author F. Scott Fitzgerald’s most famous quote is about the rarity of people being able to function while holding two conflicting ideas in their head at one time. But we are Generation Snowflake. We are special.

In a previous post I said the number one book I would recommend is Poor Charlie’s Almanack and I mentioned mental models, but I didn’t define them. In the book, Charlie shares how he believes acquiring worldly wisdom through the primary academic disciplines creates a “latticework of mental models.” Now, his principal reason for doing this is to appropriately value the future prospects of businesses better than other people so that he can make billions of dollars, primarily in the stock market. He has been doing this successfully for 50+ years.

Now, I assume many of you are more noble than I am. But, if making money is your cup of Kombucha and primary inspiration for this, we will probably expand on that in the future. Meanwhile, what guys & girls (& even gender-undecided) can get on-board with is the wide application of this concept beyond investing. It is impossible to say exactly what a business is “worth” because there are so many uncertainties, variables, and judgments required about the future, but its intrinsic value can arguably be estimated within a range. In investing, you would rather be approximately right than precisely wrong. Paraphrasing legend Benjamin Graham, you don’t need to know a guy’s weight to know he is fat.

How about we apply this same mindset to everything? We may not know exactly what something like the minimum wage should be, but maybe we can understand the consequences and possible implications of it being $5/hour (riots) and the ones when it is $20/hour ($50 cheeseburgers).

What are the models?

To the man with a hammer, every problem looks like a nail.

— Charlie Munger

A model is a representation of reality, not reality. Every idea in our head is just a model. We cannot at one time imagine the world, everything in it, and the functional relationships between those things. We have perspectives of the way we see it, which are based on a limited number of concepts.

Why should we care? The idea, concisely captured in the quote, is that one-dimensional thinking leads to us “torturing reality” to fit our current worldview (using our hammer on a screw). Developing a mental toolkit allows us to have more than one way of viewing the world, which gets us closer to reality. The latticework implies the concepts must lie on top of one another so that they are being used simultaneously (hard AF). If we have the most fundamental models, we basically create filters for the information we are increasingly flooded with while using the least amount of energy. Someone who spends a couple of months studying the underlying principles of economics is better suited to interpret new economic information than someone who has spent years reading shallow/topical economic news articles.

Here is a list of the key disciplines and an example of a model from each that has broad applications (most of which can be found in a freshman level college textbook except the one I added at the end — don’t worry, I sold most of my $300 books back to the bookstore for $7, too):

  • physics (critical mass)
  • biology (genetics)
  • psychology (the 28 psychological biases & reasons for misjudgment)
  • economics (information asymmetry)
  • engineering (feedback loops)
  • history (patterns)
  • accounting (cash flow statement)
  • business (Porter’s 5 Forces)
  • chemistry (uncertainty principle)
  • computer science (if-then statements)
  • probability/statistics (normal distribution)
  • math (systems thinking)
  • law (burden of proof)
  • travel (culture & politics)

You and I are too busy to dedicate a meaningful portion of our lives studying physics, computer science, and chemistry. We need to be at brunch, checking memes on IG, or doing whatever else it is we want to be doing. So the obvious (only?) downside to this idea is the time commitment. But Rome didn’t learn mental models in a day. If we make a reasonable effort to nail down the most fundamental concepts at first and give ourselves a realistic timeline of maybe 5-10 years, we should be able to plant a pretty good set of intellectual seeds before our mid-thirties that we will reap benefits from for the rest of our lives. We only need to learn how to ride a bike once.

(If this idea is an absolute non-starter for you, you are reading this at LIV in Miami trying to come down while people are shouting ANOTHER ONE at you in a DJ Khaled voice and you are more likely to ask for a pay cut than learn about “mental models,” at least do yourself the favor and learn the 28 psychological biases.)


The correctness of a decision can’t be judged from the outcome.

— Howard Marks

You would think I’d stop after coming up with a 5-10 year syllabus for us, but let’s briefly touch on one of the important models relevant to our discussion: probability. Another old rich white guy whose writing I like is Howard Marks of Oaktree Capital. He influenced one of the biggest changes in the way I perceive the world: thinking about the future as a probability distribution (gray) rather than a fixed outcome that can be knowable in advance (black & white). He says, “Not being able to know the future doesn’t mean we can’t deal with it. It is one thing to know what’s going to happen and something very different to have a feeling for the range of possible outcomes and the likelihood of each one happening. Saying we can’t do the former doesn’t mean we can’t do the latter.” Take for instance YouTube sensation King Curtis from Wife Swap with his chicken-nugget-heavy diet and “Bacon is good for me!” declaration. We don’t know what will happen to him, but we can safely assume his range of outcomes is unlikely to set any longevity records.

Take any situation that you can think of and how it worked out. Even though only one thing did happen, a lot of other things could have happened and those are important to appreciate. This concept is referred to as alternative histories. Let’s say we play a game where you have a 90% chance of winning and I have a 10% chance of winning. We play the game one time and I win. If a crowd was watching us without understanding the game, they may think I am better than you because I won. This is obviously a mistake. It doesn’t matter whether we play the game 1, 10, or 1,000 times, you are correct in playing against me every time regardless of the outcome. The only time this wouldn’t make sense is if there was a wager offered to me with greater than 9-to-1 odds (9x my money) if I win and/or you are unable to risk the wager (e.g. the bet was for everything you owned, in which case anything less than 100% certainty of winning would be unacceptable).

The process is more important than the outcome. Think about if our boss took our paychecks on pay-day and bought lottery tickets instead of putting them in our bank accounts. Even if we all won $10 million we should have the same reaction as if we survived a skydive and someone didn’t pack our parachute. Imagine if we replay this scenario 1,000 times and we start to think differently. If we borrow this line of thinking, it may shift the way we judge the actions of others in any field and lead to us slowing down the formation of our opinions based solely on the outcome. Further, it may make our own lives less stressful because although we can never guarantee an outcome, our intuition can take us a long way when we are asking ourselves whether we are doing the right thing that gives us the highest chance of getting what we want. We can ask: if I repeated this 1,000 times, what would likely occur?

We have covered enough ground for one day. Hopefully, I have demonstrated how mental models, and an example of one, can enhance our cognition and lead to more constructive ideas and opinions. Human nature is unlikely to change, so strong opinions and internet trolls are here to stay. But knowledge is a tide that raises all rafts, sailboats, yachts & ships.

I want to make it abundantly clear, that while your blogger here believes quite passionately that mental models are likely the best bread crumbs on the path to understanding and insight, I am a comically long way from mastering a single one of them.

Does any of this mean we are going to change overnight? No, Anastasia it doesn’t.

Firstly, it is hard. Secondly, there is a lot more paperwork to do, and thirdly, you don’t know what you are in for. You could still run for the hills. Come, I want to show you my classroom.

Additional Reading:

The Millennial Marriage Manifesto

arc-de-triomph_2014The single most important decision you will make in your life is who you decide to marry.

Your grandparents did not meet on Tinder. Your parents did not think about double-texting when they first met. And your friends in their late thirties were not interpreting emojis. Think about it. Less than 5 years ago, an eggplant was just an eggplant. The game has changed, everyone.

Relationships, psychology, and dating have interested me for as long as I can remember. They probably interest you, too, because few things provide comparable highs and lows in your own life and make for as great of conversation in others’. Since we all have a tendency to look around at the status of things at the start of a new year and it’s cuffing season, I realized more of my friends will be getting engaged and/or married this year compared to any other year since college. Also, I noticed the biggest thing separating this group and our generation from all the ones before us is the impact of technology (specifically social media and apps) on dating. Since I am fascinated with the intersection of these topics and don’t want to see (m)any marriages crumble like Mariah Carey’s New Year’s Eve performance, a discussion like this felt timely and relevant to those our age. Given the size of these subjects, forgive your unassuming blogger for failing to provide a comprehensive assessment.

From an outside perspective, your first question should be “What makes you (a single guy in his late-twenties) credible to talk about marriage?”

I have lived through divorces and listened to enough people talk about the details of their relationships that I am arguably a designated leather sofa and medical degree away from being an official player-coach psychiatrist.

Nobody gets married planning to get divorced. But ~50% get divorced. Think about that. If Blackjack and marriage have the same odds, we better figure out how to start counting cards if we don’t want to lose half our shit and turn our kids into timeshares. So what happens?

Well, we are going to date before we get married, so let’s talk about the dating & technology landscape first, because it will probably put pressure on the statistic above.

It would be easy to surprise me with a technological development, and difficult to surprise me with a dating story. We’re looking at something that changes constantly (technology) overlaid onto something that has been essentially the same forever (mate selection).

Overall, I am optimistic. I embrace this new playing field and wouldn’t want to go backwards. However, as with all change, there are trade-offs and consequences. Connecting with someone today is theoretically easier than ever. But, just because fast-food is easier than cooking does not mean it is better. When we are talking about relationships, if something is too easy, it can have unintended negative effects. The two primary downsides I currently see to our modern interconnected dating world are:

1) The Paradox of Choice. Too many choices can be overwhelming, and afterwards you get anxiety from wondering if you made the best decision. This happens to me even when I am picking out toothpaste.

2) Apathy. Winning the contest to care less (“Peak Chill”) is a Pyrrhic victory. Emotional numbness is a real risk. For 6 months in 2014, I thought I had the emotional capacity of Patrick Bateman. We are all guilty of this whether intentionally or by accident, but the acceptability of ghosting is one of the worst parts of our culture. The long-term implications of these are uncertain but likely problematic.

This new world is efficient, in that a quick-no saves time, and terrible for the same reason in that it takes time to build a relationship. And we would gladly give up our left hand before the tool that makes this all possible.

The iPhone is our remote control for the world. We can do everything on them. Hypothetically, with Uber/Lyft, Bumble/Tinder, and Favor/Postmates, you could have a stranger use their car to drive a different stranger to you, and then have yet another stranger bring you groceries, indefinitely (for a small fee). You would never even have to leave your couch. What a time to be alive. We have two options in the context of dating: go back to flip phones with the Luddites or adapt to the new reality.

While traditional ways of connecting with people will continue to exist (nothing new to comment on here) a part of this new reality is social media (Facebook, Instagram, and Snapchat) and online dating. When online dating became available to the previous generation, you would have rather been caught beating up a homeless person than admit to meeting someone on the computer. Now, with the advent of apps and attractive adopters, it is mainstream and only a matter of time before the hesitancy of saying how you met goes away. I was in a relationship, on the patio of a Dallas bar in 2013, when a friend explained Tinder to me. In three years, I have gone from laughing disbelief at a hookup app to betting that in 100 years people will think it is crazy people used to rely on chance to meet someone at a bar, college, or church. However, there will be one thing in common between the past, present, and future…

The first rule of any game is to know you are in one. I hope I’m not the first to tell you this, but dating is 100%, unequivocally, a game. Anyone who tells you they don’t play games is either in a relationship, lying, or going to get taken advantage of throughout their life. You may wish this was different, but this is not bad. Being single would become so boring. The real reason it has to be this way is because it is a form of filtering that can never go away as long as we want the best for ourselves. Suppose a girl wants to know something, such as if a guy will give her the feelings she wants (e.g. excitement, security, fulfillment). If she simply asks a guy, you know what he is going to say. Then she wastes two or three dates figuring out his favorite hobby is Pokemon, his income is dependent on local drug demand, and his biggest ambition is watching every documentary on Netflix.

So games/tests/et cetera exist to see if the person is just saying what he/she needs to to get what they want. Most of this happens subconsciously. A corollary to this is how we talk and text. We can agree we talk in code and rarely directly say what we are trying to say. If you have any doubts about this, the next time you hear a girl say “It’s fine,” let me know if “it” was “fine.”

There are levels to games and this one is no different. There are implicit and explicit rules for each medium (sometimes there are appropriate times to break the rules). Think about how texting has evolved. GIF and emoji allow for nuance that was previously unimaginable and incomprehensible to an outsider. After the most recent update, there are 1,851 different emoji, with 96 different smileys. Holy shit : )

The Rosetta Stone for Dating does not exist, and these new capabilities only amplify the potential for misinterpretation. Therefore, we are now spending time analyzing and interpreting messages, likes, and texts when there may or may not be anything to analyze or interpret. This is time not spent with the person you are trying to get to know!

While it entertains me to muse on the subjects and there obviously are pros and cons, after phases of varying duration–fun and novelty, exhaustion and boredom, and hope and despair–this will all become meaningless. Ironically, it is both necessary and irrelevant. A puzzle needs to be analyzed because it doesn’t put itself together, but the pieces don’t have to do much analyzing to know they fit together. 

Although the means have changed, it looks like most people ultimately want to find someone to (try to) spend the rest of their life with—and given that we’re working out and eating healthy, that’s probably going to be a long time. If you get married when you’re 25, stay married, and live to 90; that is SIXTY-FIVE YEARS with one person. And whether you should marry at all, well, that is another topic for another day.

At first it may seem unrealistic (it probably is) or insensitive to look at something inherently emotional in such a cerebral way, but if we don’t at least try, we are walking into the casino.

In any of the relationships I have been in, as much as I would tell myself otherwise at the time, I knew I wasn’t going to marry the girl I was dating. What was clear even then was that I considered myself too young to be making decisions for my future self.

Think back to you at 18. Then think about what 21-year-old you thought about 18-year-old you. Different person. Now think about 21-year-old you compared to you today and next thing you know you’re scrambling to delete old Facebook pictures. 18-year-old me was drawing eggplants in people’s yards with grass killer. We change and mature. This will continue to happen, and as time passes and your daily decisions accumulate, you will become a closer version of who you are going to be. However, the 50-year-old you will likely be indistinguishable from the you today and I think that is what accounts for the high probability of failed marriages. This is why it is less important to judge your partner’s objective characteristics today than it is to understand how they think about situations and make decisions.

One day you will look across either the pristine landscape or smoldering ashes of your youth and determine that you have seen and done all there is to see and do in this phase of your life and you are either open or actively looking for something more serious. This simple question can change your life: Are you the person the person you’re looking for is looking for? In other words, do you deserve the person you want to be with? The flip side to this is making sure you don’t settle. You are better than that.

Inevitably, you are going to find someone that either checks the boxes and passes the tests or makes the checklists and tests irrelevant. We’ll call this person The One. You can put the iPhone down and pick up Gary Chapman’s The 5 Love Languages. This is absolutely required reading for couples for two reasons: 1) you may think you are saying “I love you,” but it only counts if your partner feels it. This set of concepts is immensely helpful in figuring out how to communicate this to each other. 2) It has been several years since I actually read the book, but I’ll paraphrase the rules-of-thumb I remember: the first 6 months is the infatuation stage, you want to spend all your time around them, they can do no wrong and you only notice what you have in common “____ LIKES WATER TOO!” Beginning around Month 6 you can actually focus on something else besides that person, but for the next 18 months, it is still sunsets and roses. Then, approximately 2 years into the relationship, you really find out if you love someone. By then, the butterflies are dead and you are getting to see the real person. From this point on, you must be deliberate and intentional about loving them because what was natural for a couple years becomes something you have to work at.

So yeah, I generally think you should wait two years. The older you get, the more you will disagree with the two-year idea and the most common objection is, “when you know, why wait?” Because I suppose it’s as easy to say “why rush?”

For girls

  • Do not get engaged for The Ring or the Fairy Tale (pause the Bachelor and re-read this sentence). Ask a divorced woman how much she loves showing off her engagement ring and talking about her wedding now.
  • Actions have, do, and will always speak louder than words. If a guy is telling you one thing but showing you another…listen to his actions.
  • Someone else cannot make you happy. You must be happy with yourself first.

For guys

  • A trophy wife will be as meaningful to you in 30 years as the trophies in your parents’ basement.
  • If you feel pressured to get married, hit the Eject button.
  • That colossal douche Ryan Lochte actually had a moment of profundity when he said, “If you’re gonna be a man at night, you gotta be a man in the morning.”


  • Your dating life is a part of your life. You may have to be accountable for it one day.
  • Stay in shape. Your spouse didn’t marry Shrek.
  • A marriage should enhance your life. There is a condition to this: not every day. It’s going to have hard parts and if our generation has a flaw, it is we have so many alternatives in every part of our life we can be quick to quit if something doesn’t go our way.

“Marriage is the number one cause of divorce.”

People can’t predict the future, but some prepare for it better than others. One of my favorite thinkers, Charlie Munger, says, “All I want to know is where I’m going to die so I won’t go there.” In that vein, if we can figure out what causes people the most stress in relationships and what roads people took to failed ones, then we can at least anticipate some of these pitfalls and understand our future spouse’s fundamental expectations, attitudes, and beliefs before we marry them. This way we increase our chances of ending up on the right side of the coin flip. Fortunately, we do not have to experience these first-hand to learn from them.

Nietzsche said, “When entering a marriage, one ought to ask oneself: do you believe you are going to enjoy talking with this woman up into your old age? Everything else in marriage is transitory, but most of the time you are together will be devoted to conversation.” Have you ever talked to someone and it felt like trying to dribble a bowling ball? Don’t marry that person.

It may be uncomfortable to explicitly talk about the hard parts. Talking money, babies, and divorce with someone when the only thing you can hear in your head is “Oh we’ll just figure it out later,” but I promise you it’s a lot more uncomfortable to have a judge figure it out for you later.

You and your partner can consider each other co-CEOs running a business, because in a way this is what you are doing. You have income, expenses, and manage employees (kids). Business partnerships have a better chance of success if the partners have the same ideas about how the business should be run.

Now for the most important question: Are you on the same team?

This question is the essence of a relationship. Everything else will fall into place. Therapy, books, seminars, church groups, retreats; none of it ultimately matters unless you are on the same team as your partner.

You and your spouse will have problems and stressful situations. The key distinction though is whether he/she is your enemy or your teammate. People would rarely say they look at their significant other as an enemy, but accumulated resentment creates this unspoken mindset. Over time, belittling comments and disrespectful tones can make dishes left in the sink become dynamite sticks in a gas tank. If they are an enemy, once the problem goes away, they are still an enemy. If they are your teammate, you will do all of the therapy, books, seminars, retreats required until it is right because you are seeking solutions and problem-solving together.

Related to this question and equally important is: Do You Care? Some people get worn out and they simply stop caring because they feel it is beyond repair. This happens in dating too, but the stakes are higher in marriage, and people may even stay in the failed relationship. This is tragic because I can guarantee that the situation will fail to improve.

We have to acknowledge the possibility: Divorce. The best analogy I have heard for it is: Divorce is like the high-dive at a pool. You look at it from the ground and think to yourself, “It’s not that high, no problem.” When you are standing at the edge of the diving board, it is a different story and you feel your heart beating uncontrollably. Divorce can mean freedom for an abused person, but more often it is the worst experience of people’s lives. It takes a chunk of you. You will be changed. It may seem like it is too obvious to talk about, but ask your partner what situations would cause them to consider divorce. If they say, “Nothing baby! I’m yours no matter what!” then give them 5 glasses of wine, and ask again.

In another post, I recommended Pebbles of Perception by Laurence Endersen, especially because of the chapter dedicated to picking a spouse. I will simply list his Four Pillars below because he summarizes what we talked about above.

  • Take your time (because of the opening quote).
  • Don’t settle. Be aware of the most obvious warning signals and don’t expect to change your partner (or you will most likely end up changing partners).
  • Look for long-term friendship that is grounded in mutual respect and enjoyment of each other’s company.
  • Deserve a good partner.

The one I will add is related to the tendency to keep score. In all of your relationships, give more than you expect to receive.

Or, grab your iPhone and go play Blackjack.

10 Books & 5 Essays to Read Before 30

I went to a bookstore and asked the saleswoman, ‘Where’s the self-help section?’ She said if she told me, it would defeat the purpose.

— George Carlin

I will bet you a book that I have heard every excuse for why people do not read more often.

Most of the benefits are self-evident (e.g. books make you smarter and no one actively wants to be dumb), but whether it is habit, the sheer number of things competing for our attention, or something else, it surprises me how little time is spent doing it. The best reason for reading (non-fiction) books is to understand how the world works. The real test of knowledge is the real world. Books just save time. It would be prohibitively expensive, time-consuming, and dangerous for you and I to build a bridge by trial-and-error. Instead we could spend some time understanding engineering and finance which would increase our probability of success. Essentially, this “increasing our probability of success” is my motivation for reading, or maybe it is growth without a goal, or maybe it is to develop a deeper appreciation of the subject matter.

One of the critical realizations I have had is the distinction between memorizing something and learning something. The epitome of memorization is the multiple-choice test, which has been as ubiquitous in our lives as infomercials, and is great for regurgitating information then forgetting most of it. Learning, on the other hand is having information in a readily-usable format. For example: Memorizing “rate x time = distance” in physics so you can answer a question on a test is different than being able to answer your friend who asked how long it’s going to take you to get 40 miles when you’re driving 60 miles per hour; you can do some quick math to solve for time and say 40 minutes. In case you find that too simple, let’s use another one and contrast memorizing the United States presidents (trust me, this is useless knowledge) vs. being able to describe the evolution of politics from 1776 thru today.

The key concept is synthesis (I struggle with this daily). It is seeing the trees, then connecting them to understand the forest. While on trees… Elon Musk talks about knowledge as a tree. The trunk and big branches are where the basic truths and fundamentals are, and those are most likely rooted (ha) in science and often found in textbooks. Without these, there is nothing for the leaves to hang on. Some of the reading material below is dense, with a heavy focus on the trunk and branches, so that you can choose which leaves suit your interest later. Most of the books here are not Best Sellers, because our goal is to learn in the most efficient way and that means we want the knowledge to last a long time. The way to do that is learning key ideas that will carry the most weight.

If you would like to read more, then the best way to start is to follow your interests & passions. Ask yourself what is something you would like to know but don’t. That is the place to start.

Try to create a unique intellectual identity. If you consume the same information as everyone else you will most likely come to similar conclusions, which creates for a homogenous group of ideas, which is unlikely to contribute in solving existing problems. A solution to this is to incorporate authors from different disciplines, cultures, time periods, beliefs, etc.

A great resource is Farnam Street, one of the best blogs on the internet. In the way they say you should write the book you want to read, Farnam Street is the type of blog I wish I would have created. I have followed it from the near-beginning thru to its current popularity. It should be on your Favorites tab and will serve as a great place to go if you want to go to sleep smarter than when you woke up.

Absent from the list are biographies, which are highly dependent on the type of person you are interested in, and novels, which, in a similar vein, are Rorschach Tests that will have unique interpretations and applicability depending on the reader and setting.

There are certainly easier and more fun books to read, but I don’t think I am leaning too far over the railing when I say your life will be better because of them. The problem with creating a list like this is similar to having 100 children and having to pick favorites.


1. Poor Charlie’s Almanack: The Wit and Wisdom of Charles T. Munger, Expanded Third Edition
“If you skillfully follow the multidisciplinary path, you will never wish to come back. It would be like cutting off your hands.”

If I could only choose one, this is it. (Yes, it’s expensive. So are diamonds.) Charlie Munger is the longtime partner of the famed investor, Warren Buffett. If there is a trait to be admired, it is the marrying of theory and practice we talked about above. Munger is the embodiment of this concept, becoming a billionaire with his mind.

In a way, this recommendation is cheating because in a series of speeches and other thoughts, we are introduced to “mental models,” “earning the right to have an opinion,” and provided with a road map to wisdom and a prescription for lifelong learning which (you guessed it) entails more reading. I read the book in 2011 and when I review my notes from it (always take notes) I realize that while I have made progress, it will take 80-100 years to get where I would like to be.

2. The Lessons of History by Will Durant
“The first biological lesson of history is that life is competition.”

A summary of the history of the world in 100 pages. Will & Ariel Durant dedicated their adult lives to writing The Story of Civilization, an 11 volume series with 10,000+ pages. This is effectively the Cliffs Notes.

3. Principles: Life and Work by Ray Dalio
“Is this true?”

This is in the Top 3 of most influential things I have read. This book shaped my belief that we should create the life we want to live.

It may seem deceptively simple, but “is this true?” is one of the best questions we can ask in a given situation. If you spend time around organizations or watch the news, this becomes an increasingly interesting question.

4. Pebbles of Perception: How a Few Good Choices make All the Difference by Laurence Endersen
“Wishing that something which has already happened were different is pointless.”

You could read this book faster than my first three posts. If you only read it for the part on how to pick a spouse it would be well worth the energy.

5. Law 101: Everything You Need to Know About American Law, Fourth Edition by Jay M. Feinman
“The law is not a secret.”

This is probably the most tempting one on the list to skip. The law seems reserved for lawyers, but that makes something essential to our society seem inaccessible and opaque. Vagueness bothers me. If someone says (specifically with a pretentious air) “it’s complicated,” I almost throw up. “Please, educate me.” If someone knows what they are talking about, I will be grateful for the lesson, and if they do not, this will quickly become evident. Feinman lays down the law (couldn’t resist) in an approachable way that will make you sound like a “reasonable person” to your lawyer friends.

6. The Bible
“Everything is meaningless.” Ecclesiastes 1:1

Read it cover-to-cover in a version without “thou” & “thee”. There are popular one-year reading plans available on the internet. If essentially all of Western Civilization has been impacted by this collection of words, then it is worth our time to figure out what it says right?

7. Code: The Hidden Language of Computer Hardware and Software by Charles Petzold
“Code has no drawings of trains carrying a cargo of zeros and ones. Metaphors and similes are wonderful literary devices but they do nothing but obscure the beauty of technology.”

I dream of being able to explain concepts as clearly as Petzold explains computers. Although I picked this up because I had no idea how computers really worked and Amazon’s CEO says they’re going to be a big deal in my lifetime, it is on this list because it is an example of the learning process; how we go from not knowing-to-knowing anything.

8. Gödel, Escher, Bach: An Eternal Golden Braid by Douglas Hofstadter
“Meaning lies as much in the mind of the reader as in the haiku.”

Although the author himself has difficulty explaining what this book is about (because it is about so much), essentially it tries to answer the question: at what point does a collection of atoms take on a “self”? If this seems esoteric and uninteresting, blame me the messenger for inadequately selling you on the reasons you should read it, and push through it.

This is the hardest book I have read (to be clear, I am referring to grasping the concepts—the sentences are simple and well-written) and I am still working my way through it.

9. Letters from a Stoic by Seneca
“If you really want to escape the things that harass you, what you’re needing is not to be in a different place, but to be a different person.”

If you have ever had something turn out differently than you wanted, check this out. I give this book to those close to me going through hard times, and good times. Written almost 2,000 years ago, its wisdom is still as applicable today as it was then.

10. That book you told yourself you were going to read, but haven’t.

If you can tolerate my blog posts, you can finish that book.


1. This is Water by David Foster Wallace
“What it is, so far as I can see, is the truth with a whole lot of rhetorical bullshit pared away.”

David Foster Wallace was a great thinker with tragic clinical depression. His internal battles are apparent in most of his writings, but his ability to dive into the questions behind the questions is unique and wonderful. This was originally delivered as a commencement speech, and has been called one of the greatest of all time.

2. Thirty Years: Reflections on the Ten Attributes of Great Investors by Michael Mauboussin

I’ve noticed that becoming a better investor is nearly synonymous with becoming a better thinker, and often, person.

3. Consider the Lobster by David Foster Wallace
“Am I good person? Deep down, do I even really want to be a good person, or do I only want to seem like a good person so that people (including myself) will approve of me? Is there a difference? How do I ever actually know whether I’m bullshitting myself, morally speaking?”

This sneaks up on you. The title hints at it, but it becomes more than that. I’m drawn to things that force me to acknowledge actions that would be easier left unquestioned. Lobsters and moral philosophy together in one place. Who knew?

4. Letter to a Friend by Hunter S. Thompson
“As I said, to put our faith in tangible goals would seem to be, at best, unwise. So we do not strive to be firemen, we do not strive to be bankers, nor policemen, nor doctors. WE STRIVE TO BE OURSELVES.”

Once I read this, I was almost upset that I could have gone through my life without having read it.

5. How to Do What You Love  by Paul Graham
“Do what you love doesn’t mean, do what you would like to do most this second.”

Read this once every few months until you no longer need to. I still need to.


Enjoy the journey loyal readers. If you are over 30, it’s okay. You can still read them, too.

How to Run 100 Miles in a Day or So


Betty Draper: How are the [bottles] already open?
Ronnie Gittridge: Betty, we don’t want life to look difficult, now do we?
Mad Men, Season 1: Episode 9

Relatively few people want to run 100 miles at one time. That is roughly the distance from Atlanta to Chattanooga, Salzburg to Innsbruck, or mental health to insanity.

I discovered this rare breed of foot races exists two years ago at work; a co-worker came into the office on a Tuesday wearing an air boot on each foot. He had hairline fractures throughout his feet and told us what he had done that weekend. From the comfort of my chair, I recalled the extent of my running achievements: 6.2 miles in the Peachtree Road Race in Atlanta after graduating high school. Therefore, when he said he ran the Rocky Raccoon 100 in south Texas, it made an impression. Or maybe it was the broken feet and air boots. Why did he look so thrilled to be in so much pain?

Perhaps it is because everything for humans boils down to pleasure and pain. The path to each of these frequently starts with the other—you’ll either find this obvious or think about it later. Many things in our lives follow this counter-intuition. Essentially, I believe the longer you can do something painful that has a purpose, the bigger the reward. Pain with no payoff is pointless torture. So, is it pointless torture or does a 100-mile race have a purpose? Right this way.

I spent December 2015 recovering from two events: one physical in November, one intellectual in December. I wrote about it here. If you are new to this thought emporium, start there because most of it is applicable and relevant to this race and it provides proper context to this post.

Although I had sworn off 24-hour endurance races while wet and shaking in the Las Vegas desert at 3:00am last November, once you get a taste of these, nothing else is quite the same. When I got back to Dallas after Christmas, I found myself typing into Google: most scenic 100-mile races. Oregon was at the top of my list for states to visit, so when I found the Mountain Lakes 100 in Oregon on September 24th, I couldn’t resist.


I said last year the “why” is unique for everyone and although the foundational reasons for me are the same as they were 18 months ago, it has expanded and evolved. Fundamentally, it has become a metaphor for everything that I do and equanimity is the goal. But I have also realized going through this type of process helps you understand and accept reality. Eventually, running stops being about running and becomes a placeholder for the way you commit to things in your life.

My most important goal of 2016 had even less to do with running than running, but regrettably provides scant reading interest. It was passing Level 2 of the CFA program on Saturday June 4th. On January 26th, I found out I made it through Level 1 and signed up for Level 2 the following day. Four days later, the Mountain Lakes 100 registration opened. With a few clicks, I had committed myself to 300 more hours of isolation studying before June and 1,000 miles of torture running before October on top of my job and personal relationships. Hey maybe I’ll sleep next year.

DSC_4665.jpgLast year, everything was comparatively new. Waking up for Boot Camp was motivating and exciting. Running 40-70 miles per week was unchartered territory. This year, Week 1 of my Training Plan called for 40 miles. Ground Control to Major Tom. Take your protein pills and put your helmet on.

Some people hire a coach and/or nutritionist. Depending on your level within the sport, this could make sense for you. However, even with an Olympic coach, a glossy meal-by-meal nutrition plan and cutting edge ultra-marathon research, the fact remains: there is no substitute for miles on your feet.

To get the miles you have to be consistent. I try to be consistent across the areas of my life, but I often fail and the discipline doesn’t always translate to other activities. I’d rather run 10 miles than fold clothes. I never skip a run, but my clean clothes would come out of the dryer on Sunday night and stay on my bed until Thursday.

The average laundry-averse male lives 78.4 years, so if I don’t cross that finish line in September I wasted 1.3% of my life. The stakes are high. If you want to play high stakes anything, you must have a healthy respect for the possibility of failure. The higher the stakes, the higher the probability. Those who compete at the highest levels have failed. It is not that they are ok with it, quite the opposite. It’s just that they get over it quickly and move forward. The key concept is they are in the game.

How do you walk that ever-dangerously thin tightrope between confidence and over-confidence? Nothing noteworthy happens without the former, while the latter is disastrous. I had two conflicting ideas at the same time: Of my 130+ training runs, I was nervous I was unprepared (see “miles behind” below) on all of them except 3 or 4 near the end, but simultaneously there was never a doubt in my mind that I would complete the race within the 30-hour cutoff time. One of my favorite things I have obtained over the past 18 months is a deep appreciation for the fact that everything has a process. Once you figure out the process (hard), execute on the process (hard) then you have what you want (easy). A + B = C. This is the heart of engineering and a path to confidence because it is always looking to break down problems to get closer to what we want. I knew what the process was, all I had to do was execute on it.

Another principle that must be learned for successful running but is much more useful in the real world is acknowledging your emotions without being controlled by them. You grow comfortable with the wide range of emotions you experience and this teaches you about yourself. It’s ok to feel anything, as long as you keep running. The most convincing person you will ever meet is yourself telling you to take the easy way.

The carrot to keep you going is the special euphoria after a run. It is comparable to very few things, and it’s uniquely reliable. We can’t help slapping big fat unrealistic expectations onto everything we do, which sets ourselves up for inevitable disappointments (we have to keep doing this though because there are currently no known alternatives to growth). If you have never felt the runner’s high or find running boring, give it one last chance and run a half-marathon before completely writing it off. I only ask that you resist any urge to put a “13.1” sticker on your car.

Enough with the theory guac guy, let’s see your pain. I was injured in January with plantar fasciitis in my foot, a pulled calf, and tweaked knee, but recovered in February and began running short distances with regularity for a couple of months before my 28-week training plan began on April 1st.


The 6 ft. course map and Mount Jefferson the morning of the race


Miles completed: 100
Miles behind schedule: 106

Off to a good start.


An injured friend asked me to run in her place for the Dallas Skyline Half-Marathon on Sunday, May 1st. I had spent the previous 3 days between Alabama and Atlanta for my grandmother’s banger of a 90th birthday party and returned to my apartment in Dallas at midnight the night before the race. With an 8:00am start-time, Sunday morning was brutal. The guys and girls in the white jackets with stethoscopes say your max heart rate per minute should be 220 minus your age. I’m 27, so a dead sprint would be approximately 193. My average heart rate over 13.1 miles was 185. I was in bed for the rest of the day. It was hard to rationalize how out-of-shape I was. My 1:47:29 finish (8:11 min./mile) was less of a time problem than an exertion problem. If it took that much effort, a marathon would be a more reasonable September goal. The only time I’m reasonable though is at work.

Very few endurance races require a fast pace; all of them require you to keep moving. Some brave souls asked, “Can’t you just walk?” If it wasn’t a waste of your time, I would suggest trying. To meet the 30-hour cutoff time necessitates just under an 18-min. mile, and it sounds like you can walk that—you can, when you are fresh and on a flat surface. Once you inevitably slow down to a 20-min./mile uphill then you have to do a 16-min. mile to make up for it, which is probably going to require you to jog, which is more tiring than walking. You can quickly see how this feedback loop spirals into an unacceptable finishing time.


CFA Exam. I didn’t run that Saturday.

My time freed up, but it was starting to get warm.

Training outside in Texas during the summer is difficult to describe and almost unnecessary if you live here. If you’re in Dallas in June, July or August, you can leave an air conditioned room, walk through a parking deck and by the time you get to your car you’re scrambling for the “MAX COOL” button, and you never had direct exposure to the sun.

On Saturdays, I woke up between 4:00-6:00am in an attempt to finish runs by 10:30am before it got too hot. Perhaps I was a wimp, but when the temperatures were in the 90s, every mile I would have to stop for water and walk for a moment because the heat had sucked the energy out of me. One of the worst runs of the year was a solo marathon around White Rock Lake a couple times and up the White Rock Creek Trail. By the time I finished, salt was all over my face. I was dehydrated, and I looked like an extra on the Walking Dead.

Average Week

Monday: Only strength training day (gym)
Tuesday: 4 miles (shortest weekday run; if I’m going to run fast, this is the day)
Wednesday: 6-15 miles (longest weekday run)
Thursday: 6 miles
Friday: Rest day
Saturday: 9-27 miles (longest run of the week)
Sunday: Usually less mileage than Saturday; sometimes the same (preferably within 24 hours of the Saturday run, Heaven forbid your legs have a relaxing weekend)


The only exposure I had to elevation was hiking in Norway for a week.

While we were there, my girlfriend at the time said, “Did you know your eyelid is inflamed?” I said that I had vaguely noticed it. “Well, it’s been like that for a few months.” Oh great. When we got back to the US, I went to the optometrist. After a few questions he determined the cause: when I wiped the sweat out of my eyes hundreds of times over the summer, the salt irritated the eyelid, which is sensitive. Once irritated, the heat aggravates it causing it to become inflamed. A headband mitigates the problem. The solution: stop running. Add inflamed eyelid to the list of things I would have to manage until October.

Back in the US, on Saturdays I began going to the North Shore Trail, a mountain biking course in Grapevine, which would give me the closest glimpse of race conditions. A primary difference between road and trail is the absence of long straightaways in the woods. Pace changes can be measured in minutes, not seconds, when you have to navigate switchbacks and are constantly turning.


A friend encouraged me to drop out of the race and try again next year because I was behind in the recommended mileage of my training plan by 372 miles. There are a few reasons for this, but a rule-of-thumb in the sport is to limit weekly mileage increases to 10% (e.g. if you ran 40 miles this week, run 44 miles next week) and gradually build up. Ain’t nobody got time for that. In the months leading up to April, I was running ~15 miles per week. As much as you just read about me preaching the importance of executing on processes, I was behind and there is no excuse other than if I would have jumped immediately from 15 to 40, I risked injuring myself.

The peak of my training encompassed back-to-back 70-mile weeks.

Monday: Rest
Tuesday: 4 mile morning run @ SMU track (7:15 min/mile)
Wednesday: 15 miles Uptown-Downtown-Uptown-SMU morning run (9:30 min/mile)
Thursday: 6 miles night run (9 min/mile)
Friday: Rest day
Saturday: 25-27 mile trail run
Sunday: 18-20 mile run


The hard work is over. Sort of. Tapering is of interest to athletes because it is inherently counter-intuitive, but really appealing, to think doing less is doing more. When you see your suggested weekly mileage drop from 75 miles to 40 to 20 to 10 the week of the race, it’s natural to anxiously think there is no way this is the right strategy. However, the data supports it. Fine, I will run less.

Now that things were slowing down, there was time to assess the situation. Judging overall fitness on a scale of 1-20, I was probably at a 15—1 being Kenneth Bone, 20 being a Navy SEAL. If I sprinted 100 meters I would be out of breath. But if it was less than 55 degrees with no humidity, I could run 20 miles and my shirt would be dry. Throughout the training, by spending so much time on my legs and largely neglecting my upper body, I was nervous I would turn into a Scrawny Steve. It took longer than I expected, but by early September my clothes started fitting looser than I wanted.

To offset my concerns about getting too skinny, I started to feel “it”. On my runs leading up to the final week, I started to get chills from excitement. Your body knows when something like this is coming. Think coming down the stairs on Christmas morning as a child. I missed my target mileage by just under 400 miles, but I felt strong.

If worrying accomplished anything, I would love doing it. But the only influence I could have on my performance at this point was getting sleep and eating well. The only fear that was hard to shake was the uncontrollable, such as twisting an ankle on the course. Otherwise, when I landed in Portland on Wednesday, two days before my dad’s arrival, I felt completely relaxed. One of my college roommates, Scott, picked me up from the airport and showed me around the city. Over the next day and a half I did touristy things.

Late Thursday night, after taking a break from the hours of preparing my meals for both before and during the race, my best friend sent me the following text: “Motivation from a biologist: pain, fear, and exhaustion even, are just your brain’s representation of its stimuli. They do not objectively exist. They only exist in consciousness as a construct of your mind.”

I read it aloud to Scott and he said, “Yeah, except stress fractures, those are real.”

Race Weekend September 24-25, 2016


“But I don’t want to go among mad people,” Alice remarked.
“Oh, you can’t help that,” said the Cat: “we’re all mad here. I’m mad. You’re mad.”
“How do you know I’m mad?” said Alice.
“You must be,” said the Cat, “or you wouldn’t have come here.”

―Lewis Carroll, Alice in Wonderland

Course Terrain

  • 88.7 miles of single-track trails
  • 9 miles of gravel roads
  • 3 miles of jeep roads
  • .25 miles of pavement

Elevation Gain/Loss

10,800 feet of gain & 10,800 feet of loss = 21,600 feet totalmountain-lakes-100_aid-stations-detailed


Mountain Lakes 100 Course Map

It will be helpful to run through some basics first. The orange part on the map above is the course and the purple lines are roads for the crew to use between aid stations. Your crew helps with everything from refilling your water bottles and providing gear for the next segments to emotional support to get you standing up and back on the course. The Aid Stations (“AS”) are all fairly similar, with 3-10 energetic selfless volunteers providing water, PB&Js, candy, Pringles, salt tablets, pickles, and energy gels during the day, adding soup broth, rice, etc. at night. Chairs are available to sit in and some of the stations have paramedics and heated tents (beware of the chair: comfort is your enemy deep into a race).

A majority of the runners wear a hydration system (e.g. CamelBak). I use one made by Inov8 that has two ½-liter collapsible water bottles that fit into pockets by each side of my stomach with a straw that tucks into slots by my shoulder. The pack has 2 compartments in the back for additional water, clothes, or food. The engineering is unbelievable because when empty, it is essentially unnoticeable.

The course: Starting at Olallie Lake (Mile 0), you head south, completing a loop around a mountain, and return to the starting line (Mile 26). From there you head north to Clackamas (Mile 55) and complete a loop around Timothy Lake returning to Clackamas (Mile 71), then all you have to do is get back to where you started at Olallie Lake (Mile 100.95).

There are 16 aid stations that are on average 6 miles apart—the longest is Segment 3 at 9 miles (also the steepest segment), and the shortest is 3.6, the distance from Aid Station 16 to the Finish Line. Crew members are only allowed to be at 7 of the 16 aid stations, primarily due to logistical issues and road access, so make sure you can live with any gear you have for up to 30 miles.

Due to the “out-and-back” nature of the race, several of the aid stations were passed twice, stopping at it the first time heading north then again when heading south. For example Red Wolf was both AS#8 & AS#13.

Everyone has his/her individual strategy, and although I thought about it, what relevant experience would I be basing my strategy on? First off, the weather forecast showed highs that were colder than the lowest temperatures Dallas had seen in the past 6 months, and if it rained that would change everything I had planned from number of times I changed socks to the type of clothes I would wear. Next, I had never run at ~5,000 ft. altitudes, nor had I run on any long gradual inclines. And finally, this would be 46 miles longer than my farthest run. My dad often provides concise solutions and he stayed in character by saying in late August, “you’re going to have no idea until you get out there.”


Let’s pause for a moment and talk about cognitive psychology. You’ve probably heard the word “framing”. It is an information-processing bias, in which people behave differently based on the way words (information) are presented. In other words, it is everything.

A few years ago, I was lucky enough to talk to a professional golfer about the phenomenon of how golfers (people) compound mistakes unnecessarily. Just because you hit a ball in the water does not condemn you to a bad round. However, most people let the negativity impact the rest of their game and so it does condemn them to a bad round. His remedy was, instead of thinking about a round of golf as 1 game of 18 holes, think of it as 18 individual games, separating the whole into manageable pieces. This powerful framework can make all the difference in the world. When strategizing, the usefulness of the analogy became obvious and I decided that would be the way to think about the race. All I had to do was get to the next AS, which would be on average 6 miles away, and everyone can run that far. With 16 aid stations and the Finish Line, I was one segment short of a perfect comparison.

The night before was unique. The Olallie Lakes Resort is a resort in the same way a tent is a place to live. It comprised of cabins with no electricity, no cell phone service, and no plumbing. Regardless of the absence of amenities, the cabins had been booked for months. After a few attempts, we parked the miniature van on a relatively flat spot for the night (otherwise the blood would rush to one part of your body). We folded the seats into the floorboard, forced an air mattress in between the walls and slept in sleeping bags. I slept from 8:00pm to 1:00am, was up until 2:00 and then back to sleep until the alarm went off at 5:00am. 8 hours the night before a race is 3-4 more than you can usually expect.

Just before the race, tensions were high between pops and I because he realized the importance of knowing the distinctions of my gear later than he would have liked.  I was alone in the back of the mini-van covering myself with Desitin to the point my lower half looked like I was covered in icing, but this is the surest recipe to avoiding chafing and blisters.

Although the community is very friendly, you can feel the individuality of it. We all have our own way to get in the zone. Everyone there knows the next 30 hours will, to varying degrees, influence the rest of their lives. There are two types of participants: ones prepared for these year-round, here to compete and ones like me who consider a finish a win.

The beginning of the race…should you even get excited? It almost seemed like a waste of energy. I could already imagine how desperately I would crave that energy in 64 miles.

There were absolutely no excuses to be found. The conditions were perfect, the forecast showed a low of around 40 degrees and a high of 60 (perfect running weather). The furnace I trained in all summer called Texas turned out to be a #blessing because my body had grown incredibly efficient. I don’t know the math, but if your body makes 5-6 hour runs work in 100-degree heat index weather, then 50 degrees feels like a moving sidewalk with misting fans. Instead of slurping water like Moses after the desert, I was drinking it in a controlled manner like a normal human being.

The trail was so beautiful it seemed as if an ad executive was tasked with creating an advertisement of Heaven, he was given all resources imaginable and this was his final product. From an energy perspective, the first 18 miles felt easier than some 3-mile runs I have been on because I was a tourist. The scenery around every turn was postcard-worthy. However, a benefit to postcards is you don’t have to run up the mountains on them. The elevation was such a drastic departure from anything I had ever run before I laughed with another runner as I told him, “This is so bad, even if I knew it was going to be like this, I would have been too lazy to train for it.”


Segment 3: 9.35 miles & 2,600 ft. of elevation gain (photo by Sandra James)

Everything was going perfectly until halfway through mile 19, where I gained an appreciation of the vague adage about expecting the unexpected. Four other runners and I were hovering around the same pace and came to a manageable incline, which we decided to jog. As we were passing an otherwise unremarkable tree, I felt a sharp pain on my lower left calf and let out an unrestrained “mother F****R!” Before I had time to register what had happened three of the four other people yelled their version of the same sentiment. We warned the runners behind us, “Bees!” while I tallied up the number of stings—3, my favorite number.

The mindset required to complete an event like this can be summed up by the guy’s answer to my question:

“Do bee stings affect running?”

“Does it matter?”


After AS#3, there were some gunshots in the woods, and while I don’t traditionally keep track of hunting seasons I assumed that was the explanation. An older man—who was already bleeding from an apparently nasty fall—was running in front of me as we were passing another pristine lake with birds resting calmly on the water nearby when all of a sudden my body impulsively froze after hearing a gunshot aimed at the birds less than 50 yards from us; the bleeding man, the flock and I didn’t wait around to investigate. If getting stung by bees was low on my list of things to expect, guns were even lower.

I didn’t listen to music, and I only saw 2 people on the course with headphones. Part of the reason is simplicity, because that is one more thing you have to keep up with, but mainly this is a unique experience that is worthy of full attention. I came a long way for this, and good or bad, I wanted to savor the moment.

A veteran ultra-marathoner I ran with for a few miles said, “At Mile 26, you want to feel about the same as you did when you started the race.” That was true as of Mile 20, but when I returned to Olallie Lake (Aid Station #4) at Mile 26, although I felt as good as I could have expected to feel, it wasn’t like I did at the beginning. By then, Paul had arrived—he drove down that morning from Seattle to pace me for the last 30 miles. He rode with my dad to the other aid stations and would ultimately try to get as much sleep as possible before it was time to join me at the Clackamas Ranger Station (AS#12, Mile 71). He was going to have an unusual day. Because of the uncertainty around how I’d feel late in the race, who knows what time I would be there? The range was probably midnight to 6:00am. Imagine trying to get a decent night’s sleep before running 30 miles when your alarm may go off at any time over a 6-hour period and you need to be ready to run an ultra-marathon as soon as you woke up.


Aid Station #4


Spirits were high until I left AS#5 (Mile 29.65). This is when the race really starts because you won’t see your pit crew again until AS#9 (Mile 55), 25 miles later. My stomach started to hurt while I was trying to force a chicken quesadilla down, knowing I needed to get calories early on to set the foundation for the rest of the day, while walking a seemingly never-ending incline. When studying the course map and elevation changes, the big mountains draw the most attention. The little ridges in the chart go unnoticed, until you’re on them. I would get into a good rhythm then meet a hill, all but forcing me to walk it. I was alone for an hour or two.

During a stretch in the late afternoon, I noticed one of my water bottles was missing. It is the exact panic you would experience if the gates were closing to your flight and you couldn’t find your cell phone. I went back to look for it and the sun was setting. I didn’t want to think about the potential implications of not finding it. Within 5 minutes, I saw a woman was walking up the hill towards me holding it. We can board the plane.

Regarding technical trail running, everywhere you put your foot matters. I estimate that stepping on a rock or tree root impacts the bottom of your feet as much as running 2 additional miles.

The most depressing part of the race was the stretch from Mile 45 to 55. At Warm Springs (AS#7), my feet hurt. By feet I mean the ball of my right foot and by hurt I mean I started to breathe differently when my foot hit the ground. And it wasn’t just my feet. If my knees or leg muscles felt that way on a normal run, I would have stopped and taken at least a day off. You’d like to think that by crossing the 50-mile mark at AS#8 you can breathe a sigh of relief, “over halfway”. Unfortunately, that little vessel of satisfaction smashes against the rocks of reality when your GPS watch ticks to 54.01 miles over an hour later, and you realize you have over 46 miles left to run. It started to feel like pointless torture.

Speaking of GPS watches, current technology allows for precision down to the foot, yet somehow the watches will vary from the aid station signage by up to 2 miles. This was particularly frustrating for me because it was another source of uncertainty and stress. It’s like life before Google Maps, if I had paper directions and they said turn at the road on the right in 1 mile, and my odometer showed I had been driving for 2 miles with no roads on the right.

The aid stations are complicated to strategize around because they are both necessary and disruptive. Each minute spent at one is one minute not spent getting closer to the Finish Line. But if you don’t spend enough time there, what do you have to look forward to when you head to the next one? If you don’t get enough energy and rest, do you jeopardize finishing the race? The only place time goes faster than at an aid station is in one of those game show tanks with money blowing around. The elites will aim to spend 2 minutes or less at each one, which is about how long it takes me to get the 3 water bottles out of my pack, hand them to a volunteer to be filled, and put back into their pockets. If you change a piece of clothing or socks, add 3 minutes.

Nutrition for this race was similar to WTM: chicken quesadillas, CarboPro/protein shakes, and Amino Energy w/ water. In a way, I improved on making sure I got calories in, but I should have consumed more caffeine. A substantial percentage of my calories came from the aid stations. I ended up eating a lot of PB&Js in the first 40 miles, and you can only eat so many before they start their inevitable path through the pipes. The soup broth was an unexpected source of warmth. I can still remember the feeling in my palms clinching the cup. Ultimately, I guess I managed to take in 5,000-8,000 calories, but I suppose I burned somewhere in the 13,000-16,000 range.

I drank 1.0-1.5 liters of water between aid stations and then another .5-1.0 liter at each one. I also may have set a course record for number of pee-breaks. The most conservative estimate would be 35 times on the low-end. Several runners reassuringly told me this was a good sign, indicating my “system” was working well. Good, bad, or meaningless, I used the opportunity to lean against a tree to rest while my body did its thing. Again, there’s a downside to all this relaxing beyond the time lost. I could have fallen asleep on any one of those trees. If I could fall asleep standing up peeing, you can imagine how every fallen tree on the trail that runners had to climb over looked like a suite at the Ritz. I heard someone went to sleep in the woods. This takes a toll on the psyche.

At times, the isolation and exhaustion were so deep that I found myself wondering, “Is this even a real event, or am I getting Punk’d and I’m out here running through the woods for the amusement of a studio audience?” The insane part is, even if that were true and at Mile 71 you stopped the 108 people who ultimately finished the race and told them that there was some joke being played on them…they may have laughed, but they would have finished the race. You have invested your soul into it by then.

What’s it like running in the dark? Watch The Blair Witch Project. Headlamp and a trail.

Regardless of your degree of independence, I can assure you that although solitude is profoundly enjoyable, invaluable and necessary at times, people need people. Solitude turns into loneliness the moment you decide you are ready to see people and they aren’t there. The worst part of loneliness is that one second can seem like an eternity, whereas when you are with someone an eternity can seem like a second, or at least a second can still feel like a second (excluding extreme cases). This is especially true with pain and suffering. If your headlamp is the only light in the woods, the hairs on your arms are standing straight up begging for warmth, and you haven’t seen another sign of life in over an hour, the eternities start to add up.

The exhaustion had practical effects. I thought about my feet for entire segments, only to get distracted by food, music and people and forget to ask for pain medication at the aid stations. When I stopped moving, I felt the residual burn from the bee stings. Thinking back to my friend’s text, the pain and exhaustion started to feel like they in-fact objectively existed.

Talking to the other runners is a wonderful part of the event. There are no boring people out there. Whether you spent 30 seconds or 4 hours with someone, you would enjoy the time together and then you would go on your way at different paces, with only positive feelings remaining. Few areas of life offer such clean breaks.

I met Stewart, a 42-year-old from Mount Airy, NC, around 5:00pm (Mile ~40). Trekking poles in-hand he was moving, his walking pace was faster than some people’s running pace at this stage. Stewart is the type of guy you would want next to you in a war. If you hear him talk for 5 minutes, you understand without him ever having said so that there is a better chance of the mountains flattening out than him giving up. On-and-off we spent the next 30 miles, or 8.5 hours, together. In the thick Oregon forests, twilight lasts for only a moment and by 7:00pm, it was completely dark. I had talked to him for several hours before I ever saw his face. Although we were close for a long time, “together” is misleading. I had to stop to pee so frequently that it seemed like I was primarily running to catch up with him, then by the time I did I was out of gas and had to walk hard to match his pace. The further in the night we got and as our spacing grew, the less time he spent talking and the more time I wished that he found something to say.

I had heard/read about the hallucinations from other Ultra runners and had largely avoided them last year. Not this time. It was weird. Rocks were dogs and leaves were sheets with ghosts on them. When I ran past them and the light was focused on them, they were back to rocks and leaves. I needed my brain to finish, and when it started letting me down, I started questioning everything.


Volunteer at the aid station in costume

The question gets asked, “How do you keep going?” I could go on and on about Stoic philosophy and embracing the transient nature of pain, but the essence is almost unsatisfying in its simplicity and a clothing company trademarked the idea: Just Do It. Whether you are at Mile 37 or 91, are you going to take the next single step? If you are going to quit at 37, why did you do the previous 36?


The most surreal part of the weekend was the approach to the Timothy Lake Dam Aid Station. The back part of the course feels more secluded than the rest because everyone’s pace is different—145 people spread out over ~50 miles may mean hours without seeing other runners. Judging from the map, the trail is right on the water, but whether the lake is visible or not during the day is little consolation for the fact that at night it is not. This is demoralizing when you are hoping for some scenery to disrupt the monotony of night forest hiking. By this point, I was in a series of running spurts that quickly extinguished my energy and was forced to return to walking, which was more painful on my feet than running. So here I am, surrounded by darkness, and suddenly, I emerge from the woods onto what felt like a massive illuminated fashion show runway made of concrete, lined with red, white and blue stringed lights bordering the railing on the right side of the dam. On the left, there was the absolute silence of the lake. On the right, the white noise of the water rushing through the dam. The primary source of light was the stars above. It felt like I was walking through the world’s biggest planetarium; the only place I had seen this many stars blanketing the sky was in the Australian Outback 4 hours from the nearest gas station. The stars had been visible for the entire night through the trees, but I could only catch a quick glimpse without risking tripping over a rock on the trail. I took this moment to walk backwards, the only time this would be possible, allowing me to give the muscles in my legs used to go forward a brief rest and have a little enjoyment for the first time in hours.

Adding to the dream, the 3 volunteers at the aid station were dressed in Halloween costumes and warm jackets listening to music. From their attitudes, you would have guessed it was 2:00 in the afternoon, not morning. Stewart spent less than 30 seconds there, while I had to collect myself for a couple of minutes before I could convince my feet they should move again. I tried to generate heat while drinking broth and watching my breath. Aside from a brief nod at the next aid station, that was the last time I saw Stewart.

My watch died at Mile 69, nearly 18.5 hours in. It’s advertised with a 24-hour battery life. C’est la vie.

On the hunt for food & Advil

On the hunt for food & Advil

Clackamas Aid Station #12 (Mile 71) ~2:30am

This was an important Aid Station because any gear adjustments made would have to last until Mile 97, or practically the end of the race. I was on a mission and I couldn’t risk forgetting what I needed. “[Dad] take the watch and plug it in so it can charge while we’re doing everything else. I need Advil now. I need to drink at least half a bottle of [my caffeine drink] and a full protein/carb shake. Let’s make sure I have my backup headlamp.”

The EMT gave me 4 prescription-strength Advil while someone else was taking care of my water bottles. In hindsight, it was comical that he was trying to sell me on why this dosage was safe because of the amount of fluids and food passing through my body. At the time, my feet were in such pain if he offered to saw them off and put prosthetics on that would allow me to finish the race I would have heard him out.

This was also the coldest part of the night.

Paul was suited up and ready to go. The three of us came over to the van and my dad had a chair set up and everything I could possibly need laid-out across the back. I decided to stay in the same shoes, they were the newest and had the most cushioning. My jacket had sealed all the moisture inside of it so my base layer compression shirt and long-sleeve shirt were wet. I thought nothing of taking my clothes off, the cool air deceptively felt refreshing on my skin, before changing into dry shirts. I reapplied Desitin and SportShield everywhere. I slid pants on over my shorts. My watch had charged to 17%. I put my gloves back on.

I didn’t realize it but my teeth had started chattering. I chugged my shakes and we were ready to go. We started walking off towards the trail, when it hit me, “Wait, I am really cold.” If I had ignored the hypothermia symptoms last year, I would have certainly been forced to drop out of that race 9 hours into it. Knowing that, as much as I wanted to see if running would warm my blood up, it was risky so I told Paul, “I need to go back to warm up.” We got in the front seats of the van and turned the heat on. I was wearing a jacket, so if I got too warm I would start sweating and then as soon as we got outside it would be even worse than the previous cold. We stayed in there for 3-4 minutes and although the clock was ticking and this became my longest pit stop, it was worth every second.


30 miles to go.

You have to respect the pacers, especially Paul. Although he hadn’t gotten the results at the time, he had qualified for the Boston Marathon with a 3:02 marathon in San Francisco. These last 30 miles nearly matched his longest run to-date and here he was, helping me finish a race in the middle of the night that was going to be at a considerably slower pace than he was capable of. He not only did some research to discover the best way to pace someone was by running behind them—allegedly the runner feels pressure to move as fast as possible—he also had memorized most of the elevation changes, so he would suggest appropriate jogging intervals in anticipation of the hills, where I would need to walk. Having someone of sound mind that you could outsource your thinking to was indescribably helpful. Those are also some of the purest, open and honest conversations you will have.


If you want to simulate the exhaustion felt at this point in the race, put your favorite running shoes on, take 6-7 Benadryl and go for a 16-mile run.

I didn’t know it was possible to fall asleep while running. As Paul later suggested, it’s analogous to falling asleep while driving. It’s between 5:30am and 6:00am, and the only light I had seen over the past 11 hours, outside of the Aid Stations, is the 250 lumens coming from my headlamp. The specs said this thing would shine at the same intensity for 60 hours. Given it would only be dark for a fraction of that time, the risk-assessment side of my brain thought 49 hours was a pretty good margin-of-safety. Wrong. Paul told me my light was dimming. I did not want to disrupt the pace to stop and get my backup headlamp out. The intermittent hallucinations I had experienced from midnight to 3:00am gave way to full-on dreamlike states. Later, I was staring off at the trees in front of me and the trail seemed to twist and turn like an endless video game, my body effectively on auto-pilot taking each step. Unwittingly, I was enjoying the battery dying because it was getting darker, allowing my body to fall asleep. Before I knew it, I tripped over a root in the trail and my head had apparently been nodding because it popped straight up with eyes wide open, returning to consciousness. “Are you okay?” Paul asked. “Yeah,” without realizing what exactly happened…until it happened again moments later, except this time I tripped on a rock. This repeated itself a few times before I started to get irritable. How far was this damn aid station and when the hell is sunrise?

My watch died again.


Worst moment of the race.

We get to the small aid station and I sit in the closest chair. I ignore the loud music and the guy in the mascot costume trying to cheer me up. Despite the extreme tiredness, throughout the whole race I could talk coherently, in full sentences. The volunteer tries to make eye contact thru the small slit in my eyelids. I ask if there is a heating tent at this aid station. He says, “Yes, but please don’t go into it. The sun is rising and you will feel much better in just a few minutes.” I could see the sky was lighting up but I still couldn’t see anything in the woods. I felt pathetic and weak. My arms pushed me out of the chair, I stood up and we walked away from the heating tent, towards the trail.


Best moment of the race.

I could see the trees. The sun was up. There are no words to describe the contrast in mental/emotional states and energy levels that occurred the moment my body realized it was daylight. It was then that the prospect of finishing the race went from abstract to concrete. We were going to do it.

The only question was: when? The miles were slow. Our average moving pace was 17:10/mile. The Advil was barely masking the stinging in my feet, so around Mile 84 Paul gave me 2 ibuprofens and a B-12 vitamin. Surprisingly, running felt better than walking, maybe because the impact was felt over a shorter period of time. So you may think, “what a convenient problem, why don’t you just run the whole time then?” I ran out of juice. Short bursts were quickly doused. Now that it was light again, you could see the inclines up ahead.


The only substantial moves being made at this point were in one direction, down. At best you maintain. The difference between Saturday morning and Sunday morning was the difference between seeing your favorite food and seeing your favorite food after it gave you food poisoning. The scenery interested me in the way the lines of a page might interest you if you were writing 100 sentences for punishment. Sure, you notice them subconsciously, but you are really ready to finish the sentences.


Aid Station #15 (The Pinheads) Mile ~90 Chugging pickle juice to prevent/relieve cramps

At the final aid station (#16), my dad was expecting us–he had parked the van as close as possible to the tent. I changed shirts, removed any unnecessary weight from my pack and took off my pants. It was warm again. It was past 11:00am so if we were going to make a sub-28 hour finish we needed to go faster than we had all night.


Paul and me approaching Olallie Meadows, the final aid station

The last mile was longer than a mile. Imagine a movie scene where the long-lost characters are running at each other in dramatic slow motion to reconnect and the scene goes on for 11 minutes and 3 seconds. Every time we saw a turn in the trail I thought that was the final one before getting to the pavement, which would have meant we were less than 1/10th of a mile from finishing. My pace was faster than any of my previous 75 miles. Knowing I was running on fumes—physically and mentally—I was nervous that as each turn was met with more trail and rocks instead of asphalt that the disappointment would manifest itself in my body collapsing. Paul found a subtle way to get me there. “At this pace, we will finish 45 seconds before noon.”

When it came, I didn’t have to convince myself I was motivated. The trail changed to pavement. The morning silence became cowbells and cheers. The trees became people. Paul went faster so I went faster. Then I saw it.


Miles: 100.95

When I crossed the Finish Line, one of the event organizers handed me the universal finisher’s prize for 100-milers, the Belt Buckle. We took a picture, and then I went up to my dad and his smile let me know that it was over and I could smile too.

I needed food, so I inhaled a few pancakes and pieces of bacon, but existentially, I wanted nothing. My dad asked me what I wanted to drink, and they had a keg of beer and freshly-brewed coffee, two things I like. I thought I wanted both so that’s what I said, but after a sip of each, I set them down.

I took my socks and shoes off. I sat on a rock, put my feet in the cold Olallie Lake and looked up at the indifferent Mount Jefferson.

Does a 100-mile race have a purpose? Of course not.


The Financial Wisdom of Rap Music


Fred Jung: Money isn’t real, George. It doesn’t matter. It only seems like it does.
Young George: Are you gonna tell Mom that?
Fred Jung: Yeah, that’s gonna be a tricky one.

— Blow (2001)

Disclaimer: These are rap lyrics and the songs may be offensive. If Starbucks’ Red Cup at Christmas bothered you, perhaps you will find this more appealing.

My evolving theory is that rap music is the purest commercial form of ego expression (perhaps its own post one day). In the proper context, it also offers valuable financial guidance. If I can combine three things I like: finance, rap, and offering my unsolicited advice, I will take the opportunity.

The inspiration for this post was Kanye West’s recently-publicized $53 million debt burden. Before we get started, one of the most important things in your financial life is to simply care about your money—hopefully somewhere in between Paris Hilton and Ebenezer Scrooge. After all, it is the physical representation of your work, it is limited, and many people in the world are trying to shift it from your bank account to theirs. If you are under the age of 35, have less than $2 million (if you have more, be careful), and finance is not your Love Language, then these ideas may be beneficial to you. If you fall in this category and it takes you longer than 10 seconds to tell yourself 1) what your monthly cash flow is; 2) what your fixed monthly expenses are; and 3) what your net worth is, then you should figure those three things out—after you read this of course.

All right, here we go.

I got the key to the boat, I got the key to the jet 
I got the key to success: Get money, invest
Read up with the rest

— Lil’ Wayne, Over Here Hustlin’ (2006)

Work. Read. Invest.

Weezy F Baby implies here that the “F” is for finance as he succinctly provides the simplest recipe to all material pursuits. However, simple rarely means easy, especially with that “get money” part he skims over. Getting money is hard and investing it wisely is arguably harder.

The #1 thing you can do to improve your odds of success is to acquire wisdom and learn more, specifically through reading. A lot of people think it’s boring but it’s all about getting interested. If you won the $1 billion lottery in January, the next day you would have thought tax law was the most interesting thing in the world.

Book suggestion: If You Can: How Millennials Can Get Rich Slowly by William Bernstein (it’s $1 on Amazon)

Every day I’m hustlin’

— Rick Ross (2006)

Earnings power.

The difference between someone like you & me and someone like Kanye West, is if we were $53 million in debt, we would have problems coming up with that much money even if we had a shotgun. Kanye, on the other hand, has to tell his agent to schedule a 2017 tour (perhaps “Yeezus: Water into Money”) and suggest Adidas bump up the release date of his next shoe. This is called earnings power and it is highly dependent on your skills. If you are struggling to come up with blockbusting offensive lyrics and your wife’s Emoji app is making less than $1 million per minute, then you may need to get to work on your earnings power. Our society rewards specialization, so become the best at something. Imagine this scenario: there are two children and all they want to do for one year is play an instrument. The first one gets a piano and a guitar for Christmas where he spends half his time on both, and the second one gets only a guitar and spends all of his time playing it. When next Christmas rolls around which one is a band most likely to hire?

Regardless of what you choose, remember what Rick Ross is doing.

Make a little money, leave a little on the dresser

— 2 Chainz, Dresser (2014)


In order to save, you unequivocally have to spend less than you make. If you make $100 this year and you spend $101, next year you can only spend $99, unless you have cash or borrow more. However, if you borrowed the extra $1 you spent, then you also may have to pay interest to whomever lent you that $1. A 6-year-old gets this concept, but the average American household had $15,762 in credit card debt and $130,922 of any type of debt as of year-end 2015.

You have probably heard the concept of good debt and bad debt. The difference is what you’re using the debt for and how expensive it is. If you have debt with an interest rate higher than 5%, your best strategy is likely to be paying that off before thinking too much about leaving a little money on the dresser. Begin with the highest interest rate debt (e.g. credit cards) and move down to the cheaper debt (e.g. student loans). Once you have your debt level where you want it, we can begin talking about being on the other side of those interest payments and making them work for you–we will cover this in #7.

You can have anything you want. Just not everything you want. If you like bags, buy the best bag. If food is your thing, shop at Whole Foods. If you’re a stalker, buy the nicest binoculars. You get the idea. But you have to be disciplined in the other areas. It’s expensive to be a stalker trying to fit both your organic groceries and Zeiss binoculars into your Louis Vuitton bag.

How about something financially impractical, “What if I want a jet with a fur interior?” If we break that “want” into its component parts, we will find what it is you really want, which is ultimately something you can obtain with the right amount of focus and sacrifice.

I have never met anyone who regretted saving money, except gold bugs. In fact, a recent survey showed 53% of people said their biggest financial regret is not saving enough money. Well, the good news about that strange statistic is: unlike Lil’ Wayne’s Lean habit, you can control it.

I had a dream I could buy my way to heaven
When I awoke, I spent that on a necklace

— Kanye West, Can’t Tell Me Nothing (2007)

Restrict impulse purchases.

Millennials are smart and know instant gratification is old-fashioned—that’s why soft drink consumption is down in the US.

Most things financial require discipline, this one in particular. There are budgets online you can find, but entering your monthly expenses into a spreadsheet probably falls inside one of Dante’s circles. Simply be mindful of every purchase you make. One easy gimmick that works well is: when you come across something big you want, write it down. If you still want it in 60-90 days, then wait another 30 days.

I heard it’s not where you’re from but where you pay rent
Then I heard it’s not what you make but how much you spent

— Outkast, ATLiens (1996)


Everyone has an opinion on housing. If you are considering buying a house I encourage you to think deeply about that decision. If it is because you think it is an investment or you are dying to post a picture of your new home on Facebook, watch The Big Short five times. If it is for starting a family, your studio apartment is in the worst school zone in the country, and your mortgage payment is reasonable…then you may convince me that home ownership is for you. You will probably want to shoot the messenger here when he reminds you that the rule-of-thumb back in the day for what to pay for a house was 3 times your salary (i.e. if you made $100,000 your house should be ~$300,000). The only reason that number may seem low to you is because debt is extremely cheap today and the bank will give you more money. Remember too, things never cost what they cost. What I mean is most things require maintenance. My coworker owns a home and replaced an A/C unit that cost more than my annual rent. Sadly, within a year of that, his house also flooded and the repairs were about 4 years worth of my rent (insurance didn’t cover it).

To address the investment aspect, name 3 people who have moved into a less expensive home once they made a profit from selling theirs in order to use the cash. Odds are you couldn’t. However, you could probably flood my inbox with people who sold their house for more than they paid and then moved into a bigger home. The problem is, for it to be a true investment gain, you need more purchasing power than you had before you bought it, and it is very hard to use your house to buy things. When calculating your profit, you must also include all of the money you put into the house in your cost basis. Human nature is such that we are very good at remembering the points we score, but we conveniently forget some of the points scored against us.

In practice, the closest most people come to cash from the equity in their home is in the form of a home equity line of credit (“HELOC”), which—although nice—is not the same as cash.

I’m neither a housing Grinch nor a multifamily tycoon with an agenda here (I didn’t even go into the hassles of home ownership like cutting the grass). It is good to question why we do the things we do and especially the merit of what I am saying. If you have given it the appropriate amount of thought and really want a home, get one. If it feels like the next step in adulthood, perhaps you should consider alternatives.

Book Suggestion: Irrational Exuberance by Robert Shiller

Be having dreams that I’ma gangster, drinking Moets, holding Tecs
Making sure the cash came correct then I stepped
Investments in stocks, sewing up the blocks to sell rocks

— Nas, New York State of Mind (1994)


Ok, so you’ve saved all this money and you’re thinking to yourself, “Wow, this savings account earning less than 1% interest isn’t exactly Wolf of Wall Street money.” Well, there are 3 legal ways to get rich in this world:

  • Being in, or marrying into, a rich family
  • Using leverage (other people’s money) and being right
  • A combination of saving money from your labor and investing it in risky assets to earn a return. Everything that is not risk-free (e.g. Treasury Bonds) is by definition risky.

It is time to open a brokerage account.

If this is new to you, I would like to provide some practical advice to make this a realistic next step for you: I prefer the more traditional self-directed firms (Bank of America’s Merrill Edge, Scottrade, E*Trade, OptionsHouse, etc.) compared to the trendy options (Betterment, Wealthfront, etc.), but obviously do your homework and pick the option suitable to your needs. You will have to complete some paperwork and send it in, but it is worth your time.

Side note: Figure out the incentives. This applies to everything involving a fee or commission in the world. Most low-cost brokerages require no face-to-face interaction and you handle everything at your computer–they simply get a small commission for your trading activity. If you engage a financial advisor they will be more consultative and hands-on, which means they cost more. In the same way you never ask the barber if you need a haircut, you want to make sure you understand how your financial advisor gets paid (prefer fee-based over percentage-of-assets-managed if you can). Some get paid on the number of trades you make, meaning they are more interested in your activity than your wealth. Among the many questions, ask if they have their money invested in the products/fund that they are asking you to invest in. Finally, there are some financial advisors that provide much more than simple investment advice and products. I personally know some that eat/sleep/breathe their clients’ well-being and help them with everything from retirement and estate planning to taxes and trusts. This is a rare breed, so proceed with skepticism.

After you have done your homework, you will inevitably ask, “What do I invest in?” Only you can decide, but I’m about to tell you two of the most important investment ideas in the world:

  • Buy low-cost broad market index funds (e.g. Vanguard’s S&P 500 ETF; ticker symbol: VOO). This part is relatively easy.
  • Hold. This part is not so easy.

There is an entire industry dependent on people not doing those two things. The only reason money managers should get paid is if they 1) consistently earn risk-adjusted returns that beat their benchmark and/or 2) prevent you from panicking and selling at the wrong time.

There are several other blogs, books, etc. that do a great job describing the benefits of and differences between 401(k)s, IRAs, etc. but the one thing you should do immediately is open up a Roth IRA (unless you make more than $131,000) and contribute as much as you possibly can to it (up to $5,500/year). 2015 contributions can be made until April 18th, 2016! This is money that will never be taxed again.

Your money’s too young
See me when it gets older,
Ya bank account grow up

— Jay Z, Money Ain’t a Thang (1998)

Patience & compound interest.

Let’s say you are 30 years old and have $75,000. Here is what that might look like when you’re 70 under different investment scenarios—if you have ever been to a financial advisor they LOVE showing you this type of simulation:

  • 40 years compounded at 1% (current rate on Savings account at Ally): $111,665
  • 40 years compounded at 8% (hypothetical return going forward): $1,629,339
  • 40 years compounded at 9.7% (historical annual return on S&P 500 1965-2015 assuming reinvestment of dividends): $3,043,171

There are important lessons baked into these examples. Not doing something is doing something (Option 1) and it is expensive because of what you could have done with the money. If the inflation rate turns out to be more than 1% in Scenario 1, the $111,665 in the future won’t buy you what $75,000 would buy you today. All of your friends at the Glacier Peaks Retirement Community are going to be riding around in their brand new Tesla 9000 flying electric golf carts while you’re trying to sell your extra arthritis medicine at a lemonade stand.

At first glance, the 1.7% difference between Scenario 2 & 3 appears to be too small to matter, but over time that difference is $1,413,832. Just for fun and to really make the point, if you got Warren Buffett’s rate of return from 1965 to now (20.8% compounded annually) then your $75,000 would be worth $143 million. If you don’t like finance, you now know why people do.

And finally, I often hear “I’ll start saving more when I’m older.” In Scenario 3 above, the value of the investment is $913,356 when you’re 57 and grows to $3,043,171 by the time you’re 70. So those 13 years are where most of the growth occurs. If you waited until 40 to begin, to achieve the same goal would take you until you’re 80.

The main flaw in models like these is the growth doesn’t happen smoothly in real life. One year you’re up 10%, next year you’re down 6%, etc. At some point we are all tempted to sell an investment when it is down. If you are in a broad index, it is unlikely that all of the composite companies go bankrupt, so you can sleep comfortably knowing that over time, the odds are in your favor. I call this the Rip Van Winkle style of investing: Go to sleep for 30 years. But unlike Rip, you wake up with much more money than you had. Without getting too far into behavioral finance, never sell something out of fear. Figure out why it is down and whether it is temporary or permanent. Temperament is more important than intelligence in investing. 

$1,000 shoes and all they do is make my foot hurt

Que, Woodwork (2016)


It has been said that envy, not greed, makes the world go ‘round. Once you get up Maslow’s pyramid, buy things that enhance your life, not what appears to enhance someone else’s life, and especially not what the world tells you to want. When people don’t know what to do, they look to others to figure it out. I know people that couldn’t care less about watches who want a nice watch because that’s what other people do.

Another way of thinking about your expenses/habits/life is asking yourself what do you have to show for it. That can take the form of either memorable experiences or tangible possessions.

In Maryland once, I met the guy who did the landscape architecture for Sisqo after the Thong Song came out. Apparently, the lingerie lyricist spent over $1 million on the garden alone because he thought it was something celebrities should have. Unable to discover Victoria’s Secret, Sisqo had to sell his home.

All his cash, market crashed
Hurt him bad, people get divorced for that

— Kanye West, Pt. 2 (2016)

Money (or lack thereof) causes stress.

Prudently arranging your financial affairs may not get you a reality TV show, but it may give you peace of mind, provide for your family, and allow you to do things you would like to do. If you are stressed out about money, there is no Sleep Number that makes you sleep well.

When you walk out of the movie theater after watching a romantic comedy, you think that people fall in and out of love for noble reasons. Saying money doesn’t buy happiness can miss the point. If you are a billionaire and your spouse is unfaithful, the billion dollars is irrelevant. But it would cut the same whether you had one dollar or ten billion. So, you might as well have more money.

Having said that, beyond a certain financial level, you may drift into a more complex debate about the marginal benefit of adding dollars to your net worth to the sense of purpose you have in your life. If you come away from that debate feeling your only purpose is to make more money, then #10 is the last thing the Good Witch wants you to know before you walk down your road of golden bricks.


— 2 Chainz, A Milli Billi Trilli (2015)

The hook involves Mr. Chainz changing the chorus during the song from wanting a million dollars at the beginning, to a billion dollars in the middle, and finally to a trillion dollars at the end…

It is never enough.

24 Hours in the Desert: The World’s Toughest Mud Run

Plemmons_WTM 2015 Cliff Sunday

If you want to view paradise, simply look around and view it
Anything you want to, do it

— Willy Wonka, Pure Imagination (1971)

The 24 hours threw me off.

It started with a phone call in February to my friend Sam I hadn’t spoken to in years. Before the call ended, as a last-second thought, I asked how he stayed motivated to workout with a busy schedule. He said he “throws a big goal” in front of himself, having a purpose helps him stay driven from workout to workout. Of course I asked him for an example, and he said the past two years he has done a mud run at Lake Las Vegas “like the Tough Mudder events you’ve heard about, but this particular one is 24 hours.”

Like you, my initial reaction was, “that’s f***ing ridiculous.”

It took me a moment to understand what he was saying, and another to accept that it was possible. Less than 6 months before the conversation, running more than 10 minutes on the treadmill would have been a non-starter for me. So thinking about running a 5-mile obstacle course for an entire day seemed like it might as well have been swimming from New York City to London. Once I recovered from the initial shock (the second time he did the race he finished in the top 5%), I congratulated him on the massive achievement and we hung up.

Then it marinated.

World’s Toughest Mudder (“WTM”) 2015 description: The goal is to complete as many full 5-mile laps as possible in 24 hours. Each lap has 800 feet of elevation gain and 13 water obstacles, meaning roughly every ½ mile you are swimming or wading through freezing water. The temperature was 65 degrees and sunny on Saturday but dropped to 39 degrees in the middle of the night before creeping back into the 50s by noon on Sunday. The first 60 minutes is a “Sprint Period” with no obstacles. At 3:00pm an air horn goes off that can be heard around the course signaling the opening of the 21 obstacles. You must be on the course at 2:00pm on Sunday actively pursuing a lap to earn the Black Finisher Headband. You have until 3:30pm to finish your final lap.


The why is unique for everyone.

It may be useful to walk through my decision-making process, which has largely been influenced by Ray Dalio’s Principles. I want my life to be full of interesting experiences and this impacts my choices, especially big ones. I’d prefer to approach life as an endless set of projects instead of one continuous event. I never want to ask, “How did I end up here?” and be disappointed. When faced with a decision, it’s helpful to imagine you are 85 years old looking back on your life. Which choice would you regret least? Then there’s your answer.

I believe in discipline; maybe even borderline masochism. I also like the idea of delayed gratification. I’ll give up one marshmallow now to get two later. This seemed to fit the bill.

I officially signed up July 2.


The Pit on Friday Nov. 13, the day before the race

And not only so, but we glory in tribulations also, knowing that tribulation worketh patience.

Romans 5:3


Burpees. Run 10 miles 5-6 days a week for 10 weeks. (You can skip the rest of this section.)

If you want more detail… There are two parts: the obstacles and running. I don’t have a YouTube fitness channel or a protein shake sponsor but I have been playing sports for a long time and workout regularly, therefore, I figured the obstacles would be manageable, and that I should spend the majority of my time interval-cross-training and running. The goal is to catch your breath while running.

I am not a runner. At least I wasn’t. I never understood it. Runners typically look hungry and it is hard to see the appeal beyond the observation from philosopher king Ron Burgundy, “apparently you just run, for extended periods of time.” Then in late 2014, some coworkers signed up for a half-marathon that I reluctantly agreed to enter. From then on, it has essentially been impossible to stop. The post-run high is real and it is as addictive as anything else.

WTM 2015_The Pit

In her New Yorker article on running, Kathyrn Shultz said, “the essence of the experience remains invisible.” She’s right. The Katy Trail, where I did all of my weekday runs, was a great place to reflect and listen to music—highly recommended if you can avoid the armed robberies. Most of my thoughts on runs are positive and it’s one of the most enjoyable parts of the day. The first 2 miles of any run are the worst for me but it gets better from there.

Although I officially registered in July, I started training in May. That’s a long time between Day 1 and Race Day. I thought about it for hours every day. It was a weird experience because I was putting my body through amounts of pain I had never felt, and for what? An abstract idea? I had no base case to compare it to. I had never done a mud run, obstacle course, or even a marathon. For lack of a better word, it didn’t exist.

On top of this and work, I was studying for the CFA exam that has a suggested average study time of 300 hours. 2 marshmallows.


The dust

Usually I sleep well, with the worst part of my day being waking up to an alarm and pulling the covers off. For weeks in August though, I slept horribly. I would wake up in the middle of the night, paranoid and sweating, knowing I was unprepared.

If I got tired during a workout, I would feel guilty and think to myself: Oh, you’re tired? After an hour. That’s great. You’ll probably meet your expectations if you’re expecting to come in last. I needed to significantly pick up the intensity. One of my coworkers is serious about fitness and goes to Jay Johnson’s Boot Camp, a 5:30am class in various locations around Dallas. All you need is a mat, weights and water. Think P90X but outside and more aggressive. After my first class I lay on the concrete and stared at the stars until I could breathe normally. I finally felt like I was on the right path.

September & October

Now, if this was a sales pitch, here is where most of you slam the door in my face: giving up alcohol. There was no other way around it for me. I know people that don’t get hangovers. I envy them and consider that a super-power.

You young professionals out there might think, “if I gave up alcohol, I would be a millionaire.” Not so fast. All things being equal you would save money, but all things are never equal. You can throw as much money at this event as you want. During training, I went through 4 pairs of shoes. When you need a backup for every piece of gear and you realize you have spent $175 on socks and $164 on 4 pairs of compression shorts, frugality is easier said than done. There is the gear expense and then there is the time expense. Time is money, and all clichés are true.

Dating: out the window.


You have new things in your life to balance that you have never considered, like maximizing your glycogen stores and not shitting in your wetsuit. You wonder what a grown man would be doing with Desitin (the baby diaper rash cream). You almost forget what hangovers feel like.

Average weekday

4:45am: Alarm goes off. Set snooze button for 3 minutes
4:48am: Get up. Clif Bar, pre-workout shake, fruit cup
5:30am-6:30am: Boot Camp (2.5-3.5 miles)
7:15am-7:30am Drink protein/coffee shake while studying
8:30am-6pm: Work
7:00pm: Get home, Clif Bar, pre-workout shake, fruit cup
7:45pm-8:45pm: 7-mile run
9:15pm-10pm: Dinner, shower, etc.
10:30pm: Sleep

Rinse, repeat.

On Saturday mornings I would do a long run (9-20 miles), usually around White Rock Lake and Sundays go to the gym for muscle-ups (back), jump rope (endurance), and dead-hangs (grip strength for obstacles).


The diet is ironic because you would think running 7-10 miles a day you can eat whatever you want, but it’s not that simple. The longer and more intense your workouts become, the more sensitive your body is to the inputs. If I ate a huge burger at lunch, my night run would be sluggish. Mexican for dinner? Good luck running up 24 flights of stairs at the Omni at 6am.

Breakfast: Blend up an ice-coffee-protein shake, green smoothie and ~7 eggs (1 egg, 6 egg whites)

Lunch: 2 salads w/ chicken or sandwiches (always double the meat)

Dinner: Chicken/fish with brown rice/sweet potato and avocado

I keep turkey jerky, apples, and other snacks at my desk, then deli turkey and Greek yogurt in the refrigerator. I probably never went two hours without eating except when I was sleeping.

Ideally, you want to practice how you play. Living in Dallas made things like running in a wet suit or finding a hill impossible. For everything else, I tried to replicate the course conditions. Safe to say I failed at that. On some long runs, I would stop every quarter-mile to do pushups or burpees. On really long runs, I would eat a chicken quesadilla halfway through.

The peak of my training was October 17th & 18th when I ran 40 miles in a weekend, 20 on Saturday, 20 on Sunday—which made 74 miles for that week. From there, I tapered down.

Plems_WTM_Wetsuit 1

Throughout the entire process, I must have asked a hundred questions to the two guys I knew who had done this before. I would text them anywhere from 7am to 11pm asking anything from what happens if you throw up to where to clip your strobe light.

This consumed my life. I even came down with what we’ll call the Crossfit Syndrome, where you can’t help but post workout-related social media updates that no one aside from yourself cares about.

Food 1

Meal prep

Around Halloween, most of the hay was in the barn from a physical perspective, leaving the mental preparation. You want to avoid comfort because you will get soft. The 2-3 weeks before the race I stopped taking hot showers.

My friends and parents were extremely supportive. One friend, a former triathlete, wanted daily updates on workouts, without regard to his imminent heart surgery. My dad was going to leave in the middle of his two-week annual hunting trip to Illinois to fly to Vegas, be my pit crew then fly back to finish his hunt. My mom asked about the training every time she talked to me but waited until October to ask why I was doing it. She also said, “No matter what happens, you should be proud.” I said, “That’s ridiculous. Failure happens and you have to be honest with yourself about it. I’m not going to shoot an arrow and paint a target around it.”

When I finished packing I gave myself an ultimatum: you are either going to finish or go to the hospital. That meant leaving my sleeping bag at home.

Feeding Lion

The frost. It sometimes makes the blade stick.

– Gladiator (2000)

The Race

I flew into Vegas on Friday afternoon, with more luggage for a one-day race than I brought for a month-long trip to Europe. I had called Southwest on Wednesday to let them know I would be bringing several plastic bags of white powder labeled “protein,” “CarboPro,” and “caffeine” through security.

My uncle met me at the airport and drove me to Lake Las Vegas where I checked in to the hotel, which was walking distance to the course, if you had a lot of time to walk. By the time we set my tent up, my dad had flown in and taken a shuttle to the hotel. The hotel, aware of the race, had a carbo-loading buffet with pasta, pizza and salad for $20. My dad summed up the experience with his observation: this is really bad food. But it had the calories and got the job done.

Sadly, this was the same night of the Paris attacks, but due to traveling, the time difference, etcetera, I was too tired to watch TV. Fortunately, I did not have race anxiety and slept through the night until 5:30am.

For the first 4 years, the race started at 10:00am. This year they moved it to 2:00pm. I viewed this as an advantage because you would have 4 more hours of energy during the night, the most exhausting and cold part of the event. The downside to a later start is that your total waking hours would be much longer and due to the quick sunset the total time spent in a wetsuit is about 22 hours, meaning slower laps.


The Gamble: Roll a die to determine which obstacle you climb

We went to the Pit as soon as it opened at 10:00am to put my food, water, and gear in the tent. Before any race, you want to be off your feet as much as possible, not carrying cases of water and gear a half-mile. Note to Mudder Headquarters: fix this.

1:00 PM: All participants had to be at the starting line. An hour before the race? Are you kidding me? The GoPro I bought specifically for this was on the fritz so I unsuccessfully messed with it for a few minutes before talking to some veterans who had run all 4 previous WTMs.

The rule-of-thumb is if you are able to go the full 24 hours, you will most likely finish in the top 10%. That means 90% of the people will not. Judging by appearances, at least 50% of the people were more prepared than I was. They looked like they were either ex-military or serious Obstacle Course Race competitors. The only consolation I had was knowing I had put a lot of hours into getting my mind and body ready for this.

The WTM emcee started talking at 1:45PM, and I couldn’t have been more ready. The only thing I remember him saying was, “You don’t finish at the Finish Line. You finish out there. And you make it to the Finish Line.”

Lap 1 Saturday 2:00 PM (50:32 min)

My body had so much energy that when the race started I was relieved it had an outlet. Most runners say you want to be the tortoise instead of the hare, but here the hare gets rewarded at the beginning because  skipping obstacles in that first 60 minutes is an advantage, even though it’s a long race. By this point I knew my body well enough that it was going to take a few miles to warm up. At Mile 4, my calves felt the 800 feet of elevation, and I instantly regretted training in Texas. Overall, I felt good though and came into the Pit for a quick protein/Carbo Pro/chia seed shake (thanks for the suggestion Trevor Cichosz).

Lap 2 (1:10:04 min)

When I heard the air horn, I was ~6 miles in. I came to my first obstacle and thought to myself, “How many people fall off that thing?”

WTM 2015_Obstacle_Balance


Next obstacle: Operation — named after the board game. On Friday night, walking back to the hotel from the Pit I saw the “Warning: Electricity” sign next to the walls and told my uncle, “that’s going to be the easiest obstacle. They can’t take the risk someone gets electrocuted and dies.” I ate my words. You take a 10-ft hooked metal pole, put it thru a metal-lined 8-inch hole, and try to retrieve a ring on the opposite wall, all while standing in water. I grabbed the pole, put it in the hole and about 8 seconds later the pole grazed the side of the hole, sending 10,000 volts through my entire body. This happened 3 more times. I was so pissed off I went straight to the penalty: carry a 50 lb. bag of concrete a total of 300′ and through a 30′ corrugated pipe before dropping the bag off and heading to the next obstacle. I was only going to become less focused as the race went on, so I went straight to the penalty every lap.

Lap 3 (1:29:26 min)

This was the first “normal” lap with all the obstacles. I thought I would be too focused to talk. However, talking to other people is one of the only distractions from the pain. Midway through the lap I also developed the mantra that kept me motivated for the remainder of the race: Don’t bitch out.

Lap 4 (1:42:01 min)

I felt like I could destroy ISIS.

Lap 5 (1:51:48 min)

The significance of being wet and how it affects you physically and mentally cannot be overstated — it was by far the most difficult aspect of the race. Being cold is one thing. Being wet is another thing. Being cold and wet for an extended period of time is indescribable. The closest thing I can think of would be that first sensation when jumping into a pool lasting for hours.

When I crossed the finish line, I was shivering like Leo when he told Rose to never let go. I came into the Pit and I could tell by the look in my dad’s eyes that I wasn’t doing well. He knew better than to suggest I stop, but he also made me realize unless I warmed up it might be out of my control. I got into the tent, stripped everything off except my compression shorts and put a blanket around me as I sat cross-legged trying to generate heat. Somehow it worked. I noticed myself shaking less and able to think about something beyond warmth. I asked my dad to get the plastic bags ready (they help your feet slide through the neoprene leg holes). I got into the 5mm wetsuit, he helped zip me up and I put the separate hood on. My eyes were the only exposed part of my body. This all took 34 minutes and was my longest pit stop, but I needed every minute of it to get myself ready for the next 16 hours.


King of the Swingers

Lap 6 (2:02:41 min)

This was the most (relatively) comfortable lap of the entire race. I even looked forward to the water obstacles to get some fresh cold water in my suit. That changed. My muscles started cramping and locking up in areas I had never had problems with. I was tired. I had waited until about 10pm before taking any caffeine. If I took it too early I was afraid my body would stop reacting to it.  On a given day, I usually put 2 scoops of a pre-workout powder in water and take one shake before Boot Camp then one before my night run. During the race, I had 14 scoops and four 5-Hour Energy drinks. By noon on Sunday I had taken 3 days-worth of recommended caffeine servings. If anything, it helped keep me from falling asleep, but other than an initial boost from 10pm to midnight I barely noticed it.

The Cliff opened at midnight. I knew it was close because the guy next to me anxiously reported it was 11:55pm. Shortly thereafter, a race official appeared ahead of us, picked up the course marking stake and moved it a few feet to the right. It was midnight.


The 35′ free fall lasts just a moment longer than it feels like it should. What helped me was focusing on one of the spectators across the lake. Depending on your perspective, The Cliff was the easiest obstacle on the course. However, the guy with blood pouring out of his nose on Sunday morning sitting on the rescue pontoon boat unlikely had that perspective.

Lap 7 (2:20:03 min)

Then came the inevitable. I hit a wall. This was much different than running. I had the expectation that I would transcend the pain and enter this meditative state, like a monk. In a way, that is what happens, but not really. The pain is acute and sustained — the only “break” is when your mind briefly gets distracted while it’s focused on completing an obstacle. The paradox is the race would be objectively easier without the obstacles, but you need the obstacles to disrupt the monotony. Rolling under barbed wire, feeling the rocks in the mud hit your bones was not conducive to reflection as much as it was to dizziness. Crawling up an inverted tube with water spraying you in the face from the top went from comical to demoralizing. The mud in my wetsuit was getting heavier.

In nearly every part of your life, someone can lie to you. In the desert, 12 hours into this race at 2:00am, 39 degrees, soaking wet, the person next to you cannot lie. More specifically, their body can’t. The guy in the pink spandex thong is nowhere to be found. The logo on your clothes doesn’t matter because it is covered in mud. No matter how much someone loves you and wants you to succeed, they can’t climb that wall for you. It is you. Alone. Against yourself.

Plemmons_WTM 2015 Mustard

Mustard & bananas help reduce cramping

Midnight to 5am was hard. And by hard I mean the hardest thing I have ever done. While crawling through the corrugated pipes, what I wanted more than anything in the world was to lie there and close my eyes for 5 minutes.

Lap 8 (2:17:55 min)

My body was rebelling against me. The plan was to power-walk up hills and run the flat parts and downhills. Cue Mike Tyson: “Evweeone has a pwan until they get punched in the face.”

The buoyancy of the wetsuit allowed me to float on my back on the longer swimming obstacles like Hump Chuck and Statue of Liberty (75 meter swim with a lit tiki torch), which offered some relief to my legs. The lifeguards looked tired.

You question the sanity of your strategy to keep warm by urinating inside your (borrowed) wetsuit.

Lap 9 (2:04:31 min)

The most uplifting moment of my life may have been sunrise on Sunday morning. I don’t remember where I was on the course, I only remember feeling like it was going to be dark forever and seeing the light made me realize I had made it through the hardest part. Only 8 more hours to go.

Lap 10 (2:16:43 min)

I picked up my 50-Mile Brown Bib and felt like I was out of the woods. The next tangible reward was the out-of-reach 75-Mile Silver Bib and I was past the point of considering it a failure if I had to stop. It was certainly the hardest I have ever worked for a piece of clothing. My dad had no idea what he was getting into when he said he would do this. He didn’t know the 2pm rule (remember you have to be on the course pursuing a lap). I said I wanted to get 60 miles. He said, “I do not want to be out here at 3:30pm.” By this point, he had been awake for over 30 hours.

Plemmons_WTM 2015 Brown Bib

50 Miles Pit Stop

Lap 11 (2:54:35 min) Total Miles: 55

The last lap was supposed to be a celebratory one. Instead, it was the second coldest because of a costly mistake. On Lap 10 the sun was up so I decided to switch into my shorty 2mm when I got to the Pit because I was getting hot.

I forgot the wind was supposed to start at noon.  This lap had to last 2.5 hours to make it past 2pm. I intentionally took my time on this one, but the slower pace resulted in my body losing heat faster than it was making it. People said if you tried to wait by the Finish Line for a few minutes, they would make you go through and start a new lap. No thanks. With no good options, I just kept freezing. Coming up to the Cliff, the final obstacle, I was met with a 30-minute bottleneck. Listening to 50 people in front of you smack the water one-by-one was exactly the punctuation mark this damn thing needed.

2:18 PM Sunday

I make it to the Finish Line. Shaking. A girl gives me the coveted Black Headband, they take my picture, and I go directly to the medical tent to get a blanket. I can’t see my dad because the wind was blowing at least 30 mph kicking off a dust storm. When I was warm enough to leave the med tent, I found my dad and changed into dry clothes. I have never been so comfortable being naked in front of hundreds of people. My dad’s text to my mom clearly showed he shared my misery, “Thank God we stayed for the sandstorm!”

When it ends you might think there would be a celebration of some sort or at least a pat on the back. The ceremony is the next day so what you see is an anticlimactic scramble through a dust cloud to leave. I felt drunk. I was uncontrollably irritable, Siri telling me to “Turn Left Now” made me want to throw her out the window. All I could think about was getting into a bed. After getting Chipotle. I wanted to tell my dad how genuinely grateful I was for his support, but it came out as “EXTRA GUAC!”

As we walked in to my uncle’s house I felt it sink in. It was over. He and my dad were patient — I could hardly walk or talk — so they helped me get around and finish my sentences. We shared a couple laughs while we ate and checked the race results, then I hobbled into the bathroom to take a shower.

I can’t remember if any of the laps were fun. When the mud washes off though, you are a different person.




(After) 37 hours with no sleep & wetsuit-hood-hair