Why You Should Plan a Heist

You can plan a pretty picnic, but you can’t predict the weather.
-Outkast, Ms. Jackson (2000)

The operative word in the title is plan. Don’t do a heist. If you need further persuading, watch the ending of Dog Day Afternoon. Besides, you can get much more money from bankers if you give them a colorful PowerPoint presentation.

A famous joke by the (former?) comedian Dane Cook begins: what a guy wants most–even more than sex–is to be in a heist.

This thought has hung around in my mind for over a decade, but for a different reason than the one implied by the joke. It is actually a useful metaphor for three things: trust, temperament & systems thinking. Let’s call this the Heist Heuristic. (Your imagination can determine the details of your custom heist scenario).

1. Trust

We like to give people the benefit of the doubt, but sometimes we end up giving them too much credit. You can figure out the most trustworthy people in your life by asking, “If I just pulled off a heist, who would keep it a secret?” Or, if you are interviewing someone, think to yourself, “Would I trust this person to _____?” Fill in the blank with the job description, but assume that the job is their role in a heist scenario with you and if they mess it up, you spend the next 10-15 years in prison. This started out as a joke, but over the years I have noticed the clarity this deceptively simple question can provide.

2. Temperament

Remaining calm under pressure is, in my mind, one of the ultimate human qualities, because of what it entails, including the preparation required, worldly benefits over time, and the pure authenticity of it. Many things can be faked, but temperament–like wit–isn’t one of them. In the financial markets, it has been said that temperament is more important than IQ. If you have what it takes to stay calm in a heist, you most likely have what it takes to remain rational in stressful situations (e.g. deciding to hold a position while you are losing amounts of money that nearly make you throw up or while patiently watching others make money faster than you). In more prosaic affairs, maybe you will calmly talk through disagreements instead of throwing plates? Now, planning a heist alone won’t make you calm. In fact, beyond having a natural disposition, experience in high-stress situations is usually the primary way to develop this trait, but the more you have thought through potential outcomes in a scenario, they are by definition less likely to surprise you, allowing you to maintain composure. Plus, the world will often find a way to put you in such situations, giving you plenty of practice for increasingly stressful situations in the future. If you never have to use this developed skill, even better.

We will revisit temperament in future posts, especially once we introduce poker as a mental model.

3. Systems Thinking & Complex Adaptive Systems (“CAS”)

System: An organized entity made up of interrelated and interdependent parts

When I first heard the term “Complex Adaptive Systems” I thought a special kind of pretension was required to come up with something that douchey. But, like many things seemingly esoteric, once you understand it, you can never go back. Nor would you want to. This one takes a little more explaining, so you will have an opportunity to use your patience from the temperament section.

Initially, I planned on writing a separate essay on Systems Thinking, but Donella Meadows does such a good job in her book Systems Thinking: A Primer, that I would essentially be paraphrasing all of her thoughts without adding much value. If you incorporate the lessons from her book I guarantee your understanding of the world and decision making will improve. Here, I will simply introduce the concept as a reference for future conversations about CAS and explain why a heist is a convenient metaphor for situations we face.

The idea underlying systems thinking is that there are a lot of factors to consider for any given situation and, with complex adaptive systems, they interact and change. The reason this is important is because humans are necessarily reductionists and want things to be framed in the simplest terms (yes or no, good or bad, Mayweather or McGregor, and so on). Unfortunately, the world generally resists this simplification. As soon as we say something like “Real estate prices always go up!” everyone adapts to this premise by bidding up real estate values and next thing you know it’s 2008 and home prices collapse like a European soccer player after getting grazed by an opponent. The [people, in this case] adapting part is what makes it complex instead of complicated. Let’s pause for a moment to make sure we’re together with the definitions in this context. Getting gasoline to make your car move is complicated, but it’s not complexThe gasoline doesn’t figure out that it’s about to be lit on fire to sacrifice itself for the greater good of your engine, then adapt by teaming up with the other gasoline molecules and finding a way out of your tank (wild if it did though right?). Complicated processes follow a set of (generally) unchanging rules–difficult to learn, but reliable once learned. A football team is complex because the players and coaches have personalities and the way those personalities interact and evolve is inherently unpredictable. We are watching that play out right now with Tom Brady, Bill Belichick, and Robert Kraft.

Many systems take a long time for the symptoms to show up (like the negative ones of the financial crisis or the the positive ones of worldwide internet access), but in a heist the timing is accelerated and the stakes are amplified. This forces intellectual humility because as soon as we starting thinking through our plan, we realize how many factors are involved and how their interactions can drastically change the outcome. Even the simplest (most boring) of heist strategies, a note handed to a bank teller with the instructions “Put the money in the bag” could result in a wide range of outcomes depending on the teller’s mood, whether someone else notices it, and if so, is that someone a cop, and on and on we go. The consequences have consequences.

Next, and equally important, is the idea of feedback loops. Since the heist metaphor has served our purposes so far, let’s keep using it. In the movies (my favorite being The Thomas Crown Affair, followed closely by Bandits), the robbers usually use one particular feedback loop to their advantage: the spread of fear. This is an example of a positive feedback loop, where one person being afraid makes it more likely that someone else panics, which then means it’s even more likely the third person will get scared (a more tame case being more people use Instagram because more people use Instagram). From here, they can take advantage of a negative feedback loop. The classic example for a negative feedback loop is a thermostat keeping your home a certain temperature, but that example is boring, so we’re going to pick up right where we left off. Like any other working professional, random people screaming in our ear prevents us from doing good work, so after an intimidating shotgun blast through the ceiling, the hostages have gone from freaking out to being paralyzed by fear; now we need them to stay quiet. Any time one of them opens their mouth, they’re carted off to another room, never to be seen from again. This promotes stability, which is exactly what we want given that there are so many other things that could go wrong.

Returning to positive feedback loops, be mindful they can go in both directions, which may sound counter-intuitive. Suppose a college–let’s pick a random one like Penn State–had a head coach that let another coach touch boys. When people find this out, they stop wanting to play football there. The team gets worse and now even fewer people want to come play football there because no one wants to play with a bunch of losers and pedophiles (positive feedback loop to the downside). Positive feedback loops: instability (or big returns), negative feedback loops: stability.

There is much more, but as I said, I simply wanted to get you thinking about the topic if you don’t already. While there’s still no way around sounding like a pretentious douche when saying it, adding this framework to your mental toolkit will probably be beneficial in your life, although it is impossible to say exactly how. You will start noticing complex adaptive systems and feedback loops everywhere, which will likely inform your understanding of situations you’re in and how to appropriately respond. Your curiosity from there will carry you the rest of the way.

Now, I don’t want to walk by a television in a few weeks and see there’s been a 20% increase in heist activity. But what would be great is the next time you saw an armored truck, you thought about who you can trust, your ability to manage your mood, and the complexity surrounding us.

See also:

Thinking in Systems: A Primer by Donella Meadows
The Fifth Discipline: The Art & Practice of The Learning Organization by Peter Senge
What Does Charlie Munger Mean When He Says Something is a Lollapalooza? by Tren Griffin
More Than You Know: Finding Financial Wisdom in Unconventional Places by Michael Mauboussin
The Thomas Crown Affair(1999 version is better than the 1968 one, sorry Steve McQueen fans)
Bandits (2001)

An Alternative to New Year’s Resolutions

The world never tells you that you’re wrong; it only gives you outcomes. 

-Shane Parrish, Farnam Street

Kierkegaard, in Either/Or, makes fun of the “busy man” for whom busyness is a way of avoiding an honest self-reckoning. You might wake up in the night and realise that you’re lonely in your marriage, or that you need to think about what your level of consumption is doing to the planet, but the next day you have a million little things to do, and the day after that you have another million things. As long as there’s no end of little things, you never have to stop and confront the bigger questions. Writing or reading an essay isn’t the only way to stop and ask yourself who you really are and what your life might mean, but it is one good way. And if you consider how laughably unbusy Kierkegaard’s Copenhagen was, compared with our own age, those subjective tweets and hasty blog posts don’t seem so essayistic. They seem more like a means of avoiding what a real essay might force on us. We spend our days reading, on screens, stuff we’d never bother reading in a printed book, and bitch about how busy we are.

-Jonathan Franzen, Is It Too Late to Save The World?

It is safe to say the New Year’s Resolution is dead. Gyms will still likely see the customary uptick in new memberships in January, where the lines will be blurred between legs trying to escape yoga pants and a busted can of biscuits. We may eventually get lunch with that person we said we would the past 7 times we bumped into them at the grocery store. We might even “enjoy life to the fullest” (perpetually in the Top 5 most common New Year’s Resolutions)…whatever that means.

Odds are we won’t.

It would be great if The Resolution was dead because people realized that an arbitrary date was unnecessary in making necessary life changes. Instead, I think it died because doing what you say you’re going to do is hard and people get discouraged by the demands of changing their habits. At any rate, all of us are prompted by the New Year to think at least a bit about the upcoming year. Companies do this too, but their process is a little more formal. They look forward, budgeting for the upcoming year, and looking forward is what all of us must ultimately do. But many companies, and all public companies, also look backward and write letters to their respective shareholders (owners) explaining how the year went in an annual report. If you’re a stakeholder in the company or in finance, you may read them. If you have no (financial or intellectual) interest in the company, you would never read them.

Although not entirely necessary for this post, it would be worth reading one (Google your favorite public company’s shareholder letter). Management talks about the company’s financials, risks, competition, etc.–all things that impact the performance of the business.

Most businessmen I respect believe that the most appropriate place for projections is the trashcan. My own experience has certainly reinforced this idea as I have never seen a case of someone projecting that they are going to do badly (because they normally want something from the people they’re showing the projections). Therefore, we look to the past to come up with the best way to move forward. The past doesn’t predict the future, but it’s usually the best we have. Since successful investors and companies think this way I got to thinking, why don’t people do this for themselves? Replace all of the business components with a person’s. In the way that projections are often (though not always) less useful for a business than their historical performance, looking at what I did yesterday is often a better predictor of what I’m going to do tomorrow than what I think I’m going to do. At the end of 2015, I did this and found it useful. I have since shared the idea with a few more people and their reaction influenced me to share it more broadly.

Below, I’ll suggest some categories and questions to get you going, but since this is an individualistic activity, you can ignore mine and come up with your own. The temptation is to quickly skim it over and answer them in your head like a What Kind of Cheeseburger Are You? personality quiz on Facebook, but the idea here is to open up a Word document, put pen finger to paper keyboard, and get the thoughts outside of your head. If you’re still enjoying the holidays, you’re in luck because the real purpose of binge eating at this time of the year is to cause such physical lethargy you have no other option but to allow your brain to confront the bigger questions Franzen alludes to in his quote above.

We’ll start with the most popular New Year’s Resolution category. Two questions can carry a lot of weight here.

  • How did you treat your body this year?
  • Is your body fat percentage higher or lower than it was last year?
    As far as how I treated my body, one area I tried to work on in 2017 was getting enough sleep. I (used to) idolize people who can operate at a high level without much sleep, but after trying that out for a year or two, I realized this is either impossible and/or it simply doesn’t work for me. We have all heard an idiot say, “I’ll sleep when I’m dead.” When have you ever slept 4 hours each night for a week and on Friday felt like you’re performing physically or mentally at the same level as you would have if you were fully rested? Extrapolate that for a meaningful period of time and there’s no way that’s a sustainable game plan. Jeff Bezos, the boss of that online company the retail industry loves, makes getting 8 hours of sleep a top priority. If Jeff can find time to make everything happen that he does in 16 hours, I suppose I have no excuse.

Coming off the holidays, this may be a delicate one. Some people may be crying as they leave their families returning home, while others are getting to the airport 3 hours early to get away from theirs. Assuming you have family and respect them, did you strengthen your relationship with them? Any new additions? Did your roles and responsibilities within your family evolve? Do you want the same things?

There must have been a writers’ conference on New Year’s Day 2017 that determined the theme of the year was tech. Given that I can barely go to a website or read a book these days without seeing a version of how Artificial Intelligence or FANG (Facebook Amazon Netflix Google) is in the process of taking over the world, on one hand I’m convinced a robot is going to take my job and Mark Zuckerberg is going to have me tilling fields in Farmville. On the other, an automated phone system has literally never solved a problem of mine so I’m a little skeptical of impending mass unemployment. So, assuming we still have a few years left, perhaps we should ask ourselves the following: Am I getting better at what I do for work? What skills did I acquire this year? What did I create?

I was trying to order a pizza on the phone the other day from Mellow Mushroom and the guy kept calling back the wrong order to me. As I bit my lip, I was reminded of something the stoic philosopher Epictetus said 1,900 years ago, “If someone succeeds in provoking you, realize that your mind is complicit in the provocation. Which is why it is essential that we not respond impulsively to impressions; take a moment before reacting, and you will find it easier to maintain control.” There’s a related idea that when you’re right, you can afford to keep your temper, and when you’re wrong, you can’t afford to lose it. A distinguishing factor between a child and an adult is the management of our emotions. Children cry when they are hungry, adults (usually) don’t, although they have the same fundamental desire. This is a never-ending tension, as we are emotional creatures and everything that happens causes us to deal with them. The good news is we can train our emotions (think yoga). It takes some work, but over time the more we align them with rationality, the more likely we are to get what we want.

Are we really going to learn Mandarin Chinese? I have Rosetta Stone installed on my computer, but unless I move to China, the odds of me learning Chinese are about as good as Kim Jong-Un beating Dennis Rodman in basketball. There’s nothing wrong with lofty goals, but the whole idea of this post is that many resolutions are sufficiently difficult to the point people give up on many of them before they have even gotten all the glitter off. Instead of coming up with big goals, it’s amazing what can happen over time if we simply try to go to bed smarter than when we woke up. We can ask ourselves the following questions to get a feel for whether this happened or not.

  • What did you actively learn this year?
  • What books did you read?
  • Can you explain the big ideas in them to a six-year-old?

This one is easy. Take all the money you can get your hands on and buy Bitcoin! I’m 100% kidding, don’t do that. The only thing more polarizing than cryptocurrencies in 2017 was Donald Trump, so is an end-of-year blog post culturally relevant without mentioning them? I am not going to talk about them long at all here because I’m unqualified to have an opinion on Bitcoin specifically, but I can tell you that the odds of you having sustainable and repeatable financial success in something you are not an expert in are significantly low. Paraphrasing Charlie Munger from a recent interview at Michigan’s Ross School of Business, you have people being lured into the concept of easy wealth without much insight or work. Whether it’s 2017 or 2017 BC the idea of easy money is seductive. Even though it’s less fun, it pays to be skeptical. Getting rich slowly is a better goal than getting rich quickly.

Moving onto more prosaic matters, we all worked hard this year and maybe we even got paid for our work. Money buys things we want, getting things we want makes us happy, boom! Money buys happiness. If we want to be happy, we’re probably going to have to think about our finances.

  • Is your net worth (value of what you own minus what you owe) larger or smaller than it was last year? By how much? Why?
  • What was the highest and lowest quality financial outflow you had this year?
  • Did you reduce debt or add debt?
    • Most credit cards/bank statements have an Annual Summary that breaks out spending categories.

For more on personal finance, check out The Financial Wisdom of Rap Music.

Since we covered relationships earlier in the year with The Millennial Marriage Manifesto, we’ll stick to friendships here. I increasingly try to only spend time with people I like and admire. That seems obvious, but is it? The older you get the more you ask yourself the types of qualities the people you want to be around would have and realize that your friends are inevitably a reflection of yourself. You may have heard “You’re the average of the 5 people you spend the most time with.”

  • Who are those 5 people? Are they different this year than last year?
  • Did you develop deeper relationships with your existing friends? Make new ones?

While we’re talking about new friends and resolutions, in March I went to Cuba with Garrett Gravesen and a group of guys for what we ended up calling the First Annual Entrepreneurship Summit (going to start formally naming all of my vacations). Since then, he wrote a book called 10 Seconds Of Insane Courage and I had the opportunity to help edit it. Garrett lives the belief that big decisions are made in moments–10 seconds to be exact–and that your courage in those moments will determine the trajectory of your life. I’m such a big proponent of careful evaluation that the seemingly contrasting thought is compelling because regardless of how much thought goes into a decision, ultimately you must make a decision. You’ll have to read his wild stories for yourself, but viewing your decisions over the year through this lens will be illuminating.

What did you do to have fun?
This category reminds me of Kanye West’s song Paranoid “You worry bout the wrong things, the wrong things” because people who aren’t thinking about this are the ones that should and the ones who worry about whether they’re having enough fun are likely already having enough. My disposition is geared more towards delaying gratification because I feel like the payoffs are better, but the future is uncertain so we could get hit by the proverbial bus and never get to the long-term which is why we should try to have fun along the way.

In addition to the ones above, some don’t fit squarely into any particular section, like acknowledging my terrible habit of mindlessly looking at my phone too frequently. I also have started asking myself, “What is the dumbest thing I did this year?”

If you’re like me, you’ll find two things:
1. These are all interrelated.
2. By going through the process of writing these down, any changes to be made will be so glaringly obvious to you that making a formal resolution will be unnecessary. If I looked down and someone had run over my foot with a lawn mower, I hardly need to make a resolution to go to the hospital.

The opening quote from Shane Parrish at Farnam Street about outcomes is one of my favorite ideas I came across in 2017 because it seems there’s so much sensitivity in the world that the idea of someone being wrong or making a bad choice is almost taboo. It’s a subtle nudge that gets us thinking about our choices and what happens because of them while removing the black and white idea of right and wrong. Being mindful of this quote will be helpful as you go through your letter.

What would be interesting is if you made this an annual tradition and in 10 years you looked back through them. You would have a decade of personal development in front of you and a pretty good map of how you got to where you are in your life.

See also:

10 Seconds Of Insane Courage by Garrett Gravesen
Rise of the Robots: Technology and the Threat of a Jobless Futureby Martin Ford

How Kim Kardashian Got Famous: A Way to Think About Almost Everything

Got a truck full of dope, plug on the coke
Renzel done came up, prosecutors want to know
Is everything dope? Is everything dope?
How does everything go?

-Rick Ross, D.O.P.E. (2015)

Mechanism (mekuh-niz-uh m)

1. an assembly of moving parts performing a complete functional motion, often being part of a large machine; linkage
2. the agency or means by which an effect is produced or a purpose accomplished

Today, we’re going to use something boring to introduce something interesting. I’ve been reading a lot of loan documents lately (I know shoot me, right) and thank God I work with smart attorneys (corporate, not criminal, at the time of this writing) because loan agreements and the other legal documents involved when businesses want money are often hundreds of pages long, and unlike the Terms & Conditions in our Verizon contract, you actually have to read them. As important as they are, time often does not allow me to read every word. Like other bankers & businessmen, I find myself needing the information translated from Legalese into English. This is one of the reasons we happily pay lawyers.

Here’s the interesting thing: Although we generally think of legal contracts as jargon-filled and effectively unreadable to a layperson, they are still written in English. When we say, “We just signed our life away,” somewhere buried in the document spells out, in a language we can understand, exactly where we signed our life away and on what terms.

In any situation, we tend to care about what is relevant to us, right? Well, in my case I may care about what actions the bank I work for can take and when. Therefore, I need to know the exact words in the document that allow me to do that. In your phone contract, amidst all those small-print words, there are a few key ones that address the things you ultimately care about: how long it lasts, how much you pay per month, and what happens if you don’t. So if you don’t pay your phone bill, there are two important things at play: 1) The contract that gives Verizon the right to do things, like cut off your service; and 2) The physical signal no longer being sent to your phone.

Let’s call those important things mechanisms, which would fall under the bold definition at the top. If I’m you, I’m thinking “Okay, I stopped checking my newsfeed to read about mechanisms?” BUT stay with me because I think we’re onto something more general as an approach in trying to understanding almost anything. By asking in your own words or way, “What is the mechanism?” you can cut through the fluff to the substance in most situations. The substance is usually built on basics and most situations are ultimately about the basics. If someone knows, they will be able to tell you (now they may have an interest in you not knowing, which is often, in which case they won’t tell you) and if they don’t know, they will be unable to answer the question or the answer won’t make sense. There are similar phrases with a similar goal of getting to the fundamentals quickly: “What’s the point?”, “What’s the bottom-line?”, “How does it work?” Let’s look at an illustration to see the subtle differences between those and what we’re talking about.

Suppose you’re at the mall. You walk into one store and before you know it you practically need a restraining order to keep the salespeople out of your personal space while in another you could get a leg amputated and no one would be there to notice, much less answer a question on some Size 2 leggings. What explains the difference? One gets a commission and one doesn’t. You would normally call that an incentive, and it is. However, I would say that what we are more generally trying to figure out is the explanation & cause of the salesperson’s behavior (“Why they all up on me here but not there?”). In this case it happens to be an incentive (her commission or lack thereof), but it just as easily could have been one being excited after a recent promotion and the other had just gotten E. coli from lunch at Chipotle, and it is because of these different possibilities the term mechanism is more encompassing. We probably think in these terms intuitively quite a bit, like with Rick Ross in the opening quote knowing the value of dope logistics, but the more explicitly we think this way in complex or new situations the better positioned we are to figure out the truth, especially when we need to know it sooner than later. It’s this intersection of why & how that I’ve found so interesting lately.

And like most things I find interesting, someone else much smarter than me has already thought about it more than I have. I found this out when I started reading The Gene: An Intimate History by Siddhartha Mukherjee, which I picked up for two reasons: 1) my best friend is a biochemistry & genetics major getting his PhD, so I figured I better learn a little bit about genetics if I want to talk to him and 2) I liked Mukherjee’s approachable writing style in his Pulitzer-Prize winning book on cancer, The Emperor of All Maladies.

So what are the odds that before finishing the prologue I saw a variation of that engineering term that had been on my mind?

DNA is identified as the source of genetic information. The “action” of a gene is described in mechanistic terms: genes encode chemical messages to build proteins that ultimately enable form and function. 

I didn’t count, but Mukherjee goes on to use the word throughout the book, a lot. His point is that this idea of focusing on the action or mechanics was shared by many of the world’s best scientists & led to the discovery of how heredity works!

No one will ever mistake me for an expert on genetics, but an important takeaway from the book was the reinforcement of this mindset that has already drastically helped me filter what I hear & see. When someone is telling you why something is the way it is, look for the mechanisms that allow it to be that way. A complicated issue like opioid drug addiction in the United States can be better understood by looking to the possible mechanisms. Here are a few:

  • Why does this exist? Drugs make people feel good (shocker right?).
  • Why is this a problem? They have negative side effects that may eventually outweigh the positives.
  • What explains the number of people this affects? The availability of addictive substances.
  • Why are they available? Doctors frequently writing prescriptions to many patients for a variety of different conditions.
  • Why would that happen? A combination of thinking that is the appropriate solution to the patient’s underlying issue and making money by doing it.
  • What allows the businesses & doctors to do that? Their credentials, experience, governing bodies, and so on.

The reason this is worthy of our consideration is because of the time and energy spent addressing symptoms instead of root causes. Sticking with the same example, you’ll see news stories involving drugs that seem to ignore the part about people taking them because they make them feel good or the people providing the drugs making money from it.

The gut reaction that this is all too obvious to talk about is due to something called the illusion of explanatory depth (“IOED”) which is a confident, but mistaken feeling of knowing. If you ask 50 people if they know how a washing machine works, they’d probably say yes. But if you asked them to give detailed step-by-step instructions on how it works, most would look at you like Simple Jack in Tropic Thunder. If we are aware of this IOED, we will instinctively start looking for ways to fill in those gaps.

If you do this for a while, as weird as it sounds at first, a couple of things will start to happen.
1: You will become dissatisfied with things that have vague mechanisms and will push for greater clarity (e.g. “Oh, so you two were just hanging out?”)
2: You will start realizing that many of these hinge on the definition of a single word or phrase. Recall Bill Clinton and his famous “Depends on what your definition of is is.”

Arguably, doing anything other than focusing on the mechanisms is superfluous.

Using that same idea, we can look at our own work. Most of us would like to be organized for various reasons, and we could likely see benefits from it over time, but they are indirect (I use this as an example because I highly value organization, so I’m challenging myself). However, can you imagine me sitting in my office thinking “My desk is clean, so the deals should start rolling in.”? When seen from that perspective, unless you are part of a cleaning crew, it’s clear that being organized isn’t the mechanism. When we acknowledge what generates the final service or product we provide, we will avoid potentially misleading ourselves about our productivity. On a related note, I think. “Why don’t we report on our earnings call how many hours we spent in our offices?” We all remember from college that there is a big difference between going somewhere to study and actually studying.

Some other simplified examples:

  • Fewer drunk driving accidents
    • The mechanism: Uber & Lyft
  • Why no one says anything contradicting the boss, when it’s evident he’s wrong
    • The mechanism: The threat of the boss firing the person who said it
  • How Apple can charge $1,000 for a phone (at its current volume)
    • The mechanism: Breaking up one big payment into more manageable monthly payments
  • Capitalism:
    • The mechanism: Forceful protection of personal property
  • Traffic
    • The mechanism: brakes (can’t have traffic if you never use your brakes! Although this is impractical, it’s a useful framework for thinking about how people should drive, which would be at a speed that requires everyone to use their brakes as little as possible. Obviously, something like traffic is a complex situation and it is influenced by several factors like number of drivers, wrecks, construction, traffic lights, etc. but this is actually one of the purest examples of a mechanism because all of those other factors ultimately lead to you hitting your brakes. If your goal was to reduce traffic, you would be mindful of this every time you considered adding a new intersection with a traffic light.)

On one hand, this is common sense. On the other, there are structural reasons why people don’t want you to know the mechanisms of many things (e.g. Coke recipe), making it even more important that you are able to figure them out for yourself. Now that we’ve seen how this looks in everything from rap songs & genetics to loan documents & drugs, please remember your humble blogger when thou art upon the podium receiving thy Nobel Prize.

I’ll let you determine the mechanism for Kim’s fame.

See also:
The Gene: An Intimate History by Siddhartha Mukherjee
Thing Explainer: Complicated Stuff in Simple Words by Randall Munroe

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 weren’t 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’re 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’s 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’s 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’re 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’s getting that summer internship.

Having said that, there’s 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 can’t 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’s like a bucket list, but for while you’re 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’s not a good look). Having said that, the people you have in your life profoundly impact the quality of it and I’ve 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’s 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 don’t know ourselves and therefore our true wants and/or 2) choosing something we want today means in 5 years we won’t be able to have 10 things we want then. Let’s make sure we’re 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 & action you ever make then who cares where you end up?

Here’s 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’s what people do.” Well, pretend it’s 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 don’t 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 don’t 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’s 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 don’t 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’re spreading yourself too thin and you are by definition not focused. I practice what I preach, but this one is difficult for me.

I’ll 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’s pathetic and then there’s 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 don’t 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’re 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’m 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, don’t 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’s 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 wasn’t 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 won’t 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’m sure we can agree that increasing degrees of freedom is better. There is a paradox here. When you were a kid you didn’t have a driver’s license and now that you’re an adult you don’t 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’s 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’m saying or more likely, has just realized how doing some of these things could have prevented pain. It’s crucial to be clear on these two possibilities. One, spontaneity is great. The best day of your life isn’t 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’re simply aiming for better-than-random conditions for ourselves. 

See also:
The Design of Everyday Things by Dan 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 an 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’re doing that you become one with it. For example, it’s 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’re 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. What’s funny, is I used to think I wanted to be happy. But, what I realized is that satisfaction is actually superior to happiness because you can’t pursue happiness directly. Happiness is what’s left after you’ve done something else. I’d imagine that a NY firefighter on 9/11 would not describe himself as happy, but would feel fulfilled and satisfied by saving lives. There’s 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’s 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’s 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 can’t 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’s 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’m 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’s 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’s 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’ll 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’s 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’s 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 don’t get it, which can’t be the case. If we can gravitate towards the center over time, I think we’ll 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 don’t need much of it in your life. This reduces the number of things you want, which almost literally means you’ll 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 7 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’m not talking about a better society in the abstract Let’s Love Everyone sense. I’m 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 is under 30, 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’ve thought about it. Our opinions are not equal and I haven’t earned the right to say much on the topic. “Well that’s 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’s 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 tradeoffs (shades of gray). The more objective answers we accumulate, the more equipped we are to assess those tradeoffs.

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’s Sunday or not.
2) Many people are trying to fool you. This is the bigger one– If we’re too open-minded we’ll 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’s 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’re not done yet) to suggest we should know what we’re talking about and consider the other side of an argument. There’s 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!!!!!” They’ve pounded the same ideas into their head for so long and only surrounded themselves with people like them that they’ve ruined their mind. I’m not in love with too many ideologies, but I can kind of empathize: if avocado availability were threatened, I’d 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’s 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’re Generation Snowflake. We’re 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 it, 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’d rather be approximately right than precisely wrong. You don’t need to know a guy’s weight to know whether he is fat or not.

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’s $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’s 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)

Now 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’re 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’re 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 I like reading 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’s 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 does 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’re 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’ve demonstrated how mental models, and an example of one, can enhance our cognition and lead to more constructive ideas and opinions. Human nature won’t change, so strong opinions and internet trolls aren’t going anywhere. 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’re going to change overnight? No, Anastasia it doesn’t.

Firstly, it’s hard. Secondly, there’s a lot more paperwork to do, and thirdly, you don’t know what you’re 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_2014“The 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.