How to Pick a Career (That Actually Fits You)

Hey readers! Quick note before we jump in:

This is a post about something I’ve been wanting to write about forever: careers. Society tells us a lot of things about what we should want in a career and what the possibilities are—which is weird because I’m pretty sure society knows very little about any of this. When it comes to careers, society is like your great uncle who traps you at holidays and goes on a 15-minute mostly incoherent unsolicited advice monologue, and you tune out almost the whole time because it’s super clear he has very little idea what he’s talking about and that everything he says is like 45 years outdated. Society is like that great uncle, and conventional wisdom is like his rant. Except in this case, instead of tuning it out, we pay rapt attention to every word, and then we make major career decisions based on what he says. Kind of a weird thing for us to do.

This post isn’t me giving you career advice really—it’s a framework that I think can help you make career decisions that actually reflect who you are, what you want, and what our rapidly changing career landscape looks like today. You’re not a pro at this, but you’re certainly more qualified to figure out what’s best for you than our collective un-self-aware great uncle. For those of you yet to start your career who aren’t sure what you want to do with their lives, or those of you currently in the middle of your career who aren’t sure you’re on the right path, I hope this post can help you press the reset button on your thought process and get some clarity.

Finally, it feels very good to put this post up. It’s been way, way too long. The last year has been pretty frustrating for me and anyone who likes Wait But Why—a lot of build-up of ideas with none of the satisfying release of those ideas on the blog (most of my last year has been spent working on another, way longer post). I’m hoping this WBW Dark Ages era is nearing its end, because I miss hanging out here. Thanks, as always, to the small group of ridiculously generous, ridiculously patient patrons who have stuck with us through such a slow period.

– Tim

PDF: If you want to print this post or read it offline, the PDF is probably the way to go. You can buy it here.

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Your Life Path So Far

For most of us, childhood is kind of like a river, and we’re kind of like tadpoles.

We didn’t choose the river. We just woke up out of nowhere and found ourselves on some path set for us by our parents, by society, and by circumstances. We’re told the rules of the river and the way we should swim and what our goals should be. Our job isn’t to think about our path—it’s to succeed on the path we’ve been placed on, based on the way success has been defined for us.

For many of us—and I suspect for a large portion of Wait But Why readers—our childhood river then feeds into a pond, called college.1 We may have some say in which particular pond we landed in, but in the end, most college ponds aren’t really that different from one another.

In the pond, we have a bit more breathing room and some leeway to branch out into more specific interests. We start to ponder, looking out at the pond’s shores—out there where the real world starts and where we’ll be spending the rest of our lives. This usually brings some mixed feelings.

And then, 22 years after waking up in a rushing river, we’re kicked out of the pond and told by the world to go make something of our lives.

There are a few problems here. One is that at that moment, you’re kind of skill-less and knowledge-less and a lot of other things-less:

But before you can even address your general uselessness, there’s an even bigger issue—your pre-set path ended. Kids in school are kind of like employees of a company where someone else is the CEO. But no one is the CEO of your life in the real world, or of your career path—except you. And you’ve spent your whole life becoming a pro student, leaving you with zero experience as the CEO of anything. Up to now, you’ve only been in charge of the micro decisions—”How do I succeed at my job as a student?”—and now you’re suddenly holding the keys to the macro cockpit as well, tasked with answering stressful macro questions like “Who am I?” and “What are the important things in life?” and “What are my options for paths and which one should I choose and how do I even make a path?” When we leave school for the last time, the macro guidance we’ve become so accustomed to is suddenly whisked away from us, leaving us standing there holding our respective dicks, with no idea how to do this.

Then time happens. And we end up on a path. And that path becomes our life’s story.

At the end of our life, when we look back at how things went, we can see our life’s path in its entirety, from an aerial view.

When scientists study people on their deathbed and how they feel about their lives, they usually find that many of them feel some serious regrets. I think a lot of those regrets stem from the fact that most of us aren’t really taught about path-making in our childhoods, and most of us also don’t get much better at path-making as adults, which leaves many people looking back on a life path that didn’t really make sense, given who they are and the world they lived in.

So this is a post about path-making. Let’s take a 30-minute pre-deathbed pause to look down at the path we’re on, and ahead at where that path seems to be going, and make sure it makes sense.

The Cook and the Chef—Revisited

In the past, I’ve written about the critical distinction between “reasoning from first principles” and “reasoning by analogy”—or what I called being a “chef” vs. being a “cook.” Since writing the post, I notice this distinction everywhere, and I’ve thought about it roughly 2 million times in my own life.

The idea is that reasoning from first principles is reasoning like a scientist. You take core facts and observations and use them to puzzle together a conclusion, kind of like a chef playing around with raw ingredients to try to make them into something good. By doing this puzzling, a chef eventually writes a new recipe. The other kind of reasoning—reasoning by analogy—happens when you look at the way things are already done and you essentially copy it, with maybe a little personal tweak here and there—kind of like a cook following an already written recipe.

A pure verbatim recipe-copying cook and a pure independently inventive chef are the two extreme ends of what is, of course, a spectrum. But for any particular part of your life that involves reasoning and decision making, wherever you happen to be on the spectrum, your reasoning process can usually be boiled down to fundamentally chef-like or fundamentally cook-like. Creating vs. copying. Originality vs. conformity.

Being a chef takes a tremendous amount of time and energy—which makes sense, because you’re not trying to reinvent the wheel, you’re trying to invent it for the first time. Puzzling your way to a conclusion feels like navigating a mysterious forest while blindfolded and always involves a whole lot of failure, in the form of trial and error. Being a cook is far easier and more straightforward and less icky. In most situations, being a chef is a terrible waste of time, and comes with a high opportunity cost, since time on Earth is immensely scarce. Right now, I’m wearing J. Crew jeans and a plain t-shirt and a hoodie and Allbirds shoes, because I’m trying to conform. Throughout my life, I’ve looked around at people who seem kind of like me and I’ve bought a bunch of clothes that look like what they wear. And this makes sense—because clothes aren’t important to me, and they’re not how I choose to express my individuality. So in my case, fashion is a perfect part of life to use a reasoning shortcut and be a cook.2

But then there are those parts of life that are really really deeply important—like where you choose to live, or the kinds of friends you choose to make, or whether you want to get married and to whom, or whether you want to have kids and how you want to raise them, or how you set your lifestyle priorities.

Career-path-carving is definitely one of those really really deeply important things. Let’s spell out the obvious reasons why:

Time. For most of us, a career (including ancillary career time, like time spent commuting and thinking about your work) will eat up somewhere between 50,000 and 150,000 hours. At the moment, a long human life runs at about 750,000 hours. When you subtract childhood (~175,000 hours) and the portion of your adult life you’ll spend sleeping, eating, exercising, and otherwise taking care of the human pet you live in, along with errands and general life upkeep (~325,000 hours), you’re left with 250,000 “meaningful adult hours.”3 So a typical career will take up somewhere between 20% and 60% of your meaningful adult time—not something to be a cook about.

Quality of Life. Your career has a major effect on all the non-career hours as well. For those of us not already wealthy through past earnings, marriage, or inheritance, a career doubles as our means of support. The particulars of your career also often play a big role in determining where you live, how flexible your life is, the kinds of things you’re able to do in your free time, and sometimes even in who you end up marrying.

Impact. On top of your career being the way you spend much of your time and the means of support for the rest of your time, your career triples as your primary mode of impact-making. Every human life touches thousands of other lives in thousands of different ways, and all of those lives you alter then go on to touch thousands of lives of their own. We can’t test this, but I’m pretty sure that you can select any 80-year-old alive today, go back in time 80 years, find them as an infant, throw the infant in the trash, and then come back to the present day and find a countless number of things changed. All lives make a large impact on the world and on the future—but the kind of impact you end up making is largely within your control, depending on the values you live by and the places you direct your energy. Whatever shape your career path ends up taking, the world will be altered by it.

Identity. In our childhoods, people ask us about our career plans by asking us what we want to be when we grow up. When we grow up, we tell people about our careers by telling them what we are. We don’t say, “I practice law”—we say, “I am a lawyer.” This is probably an unhealthy way to think about careers, but the way many societies are right now, a person’s career quadruples as the person’s primary identity. Which is kind of a big thing.

So yeah—your career path isn’t like my shitty sweatshirt. It’s really really deeply important, putting it squarely in “Definitely absolutely make sure to be a chef about it” territory.

Your Career Map

Which brings us to you. I don’t know exactly what your deal is. But there’s a good chance you’re somewhere in one of the blue regions—

—which means your career path is a work in progress.4

Whether you’re yet to start your career or well into it, somewhere in the back of your mind (or maybe in the very front of it) is a “Career Plans” map.

We can group map holders into three broad categories—each of which is well-represented in the river, in the pond, standing on the shore, and at every stage of adult life.

One group of people will look at the map and see a big, stressful question mark.

These are people who feel indecisive about their career path. They’ve been told to follow their passion, but they don’t feel especially passionate about anything. They’ve been told to let their strengths guide them, but they’re not sure what they’re best at. They may have felt they had answers in the past, but they’ve changed and they’re no longer sure who they are or where they’re going.

Other people will see a nice clear arrow representing a direction they feel confident is right—but find their legs walking in a different direction. They’re living with one of the most common sources of human misery, a career path they know in their heart is wrong.

The lucky ones feel they know where they want to go and believe they’re marching in that direction.

But even these people should pause and ask themselves, “Who actually drew this arrow? Was it really me?” The answer can get confusing.

I’m pretty sure all of these people would benefit from a moment of career path reflection.

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