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 are going to be tall. If you were born in the US, you have access to air conditioning and medicine. If your mom is the CEO of the corporation you want to work for, guess who’s getting that summer internship.

Having said that, there is room for decision making in determining outcomes. The problem is, most people shape their lives without knowing it through the decisions they make every day. I 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 are living normally, not just before you die.

Like any idea, this can be carried to extremes. Our actions are rarely insulated to ourselves, so don’t mistake this to be suggesting that you surround yourself with people who enable you to live in your own unchecked fantasy (you know someone who does this and it’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 do not know ourselves and therefore our true wants and/or 2) choosing something we want today means we will be unable to have 10 things we want in five years. Let’s make sure we’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 is a hypothetical, but useful, example of things getting away from us. Suppose a guy says, “I want a big house in a good school district because my wife wants one, that would be great for my family, and that’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 do not feel the clock of their life ticking or often feel like victims of circumstances will not find this concept compelling.

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

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

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

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

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

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

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

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

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

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

See also:
The Design of Everyday Things by Dan Norman

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

Stumbling on Happiness by Daniel Gilbert

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