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because it’s super clear he has very little idea what he’s talking about and that everything he says is like 45 years outdated.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.

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.

The Okay But Why Do You Think You Can Help Me With My Career Reflection You Draw Stick Figures for a Living Blue Box

Extremely fair question. One thing I always ask myself as I pick topics to write about is, “Am I qualified to write about this?” Here are the reasons I decided to take on this topic:

1) I have spent most of the last 20 years in a perpetual state of analyzing my own career path.

2) My path has taken a lot of turns—from wanting to be a movie star when I was 7 to wanting to be the president when I was 17 to wanting to write film scores when I was 22 to wanting to be an entrepreneur when I was 24 to wanting to write musicals when I was 29 to most recently wanting to be a writer-ish guy.

3) After being pretty all over the place about my career path for most of my life, I actually love my job now. That’s always subject to change, but being able to look at the decision-making processes that led me to confusing or frustrating places, side by side with the decisions that led me to a more fulfilling place, has offered me some wisdom on where people tend to go wrong.

4) On top of having my own story to look at, I’ve had a front-row seat for the stories of my dozen or so closest friends. My friends seem to share my career path obsessiveness, so between observing their paths and talking with them about those paths again and again along the way, I’ve broadened my views on the topic, which helps me to distinguish between the lessons that are my-life specific and those that are more universal.

5) Finally, this isn’t a post about which careers are better or worse than others or which career values are more or less meaningful—there are lots of social scientists and self-help authors out there with good data on that, and I’m not one of them. It’s instead a framework that I think can help a career-path reflector better see their own situation, and what really matters to them, clearly and honestly. This framework has worked really well for me, so I think it can probably be helpful for other people too.

Now that you’ve taken a fresh look at your Career Plans map, along with whatever arrow may or may not be on it, put it down and out of sight. We’ll come back to it at the end of the post. It’s time now for a deep dive—let’s think about this from scratch. From first principles.

In the cook-chef post, I designed a simple framework for how a chef makes major career choices. At its core is a simple Venn diagram.

The first part of the diagram is the Want Box, which contains all the careers you find desirable.

The second part of the diagram is the Reality Box. The Reality Box is for the set of all careers that are realistic to potentially achieve—based on a comparison, in each case, between your level of potential in an area and the general difficulty of achieving success in that area.

The overlapping area contains your optimal career path choices—the set of arrows you should consider drawing on your Career Map. We can call it the Option Pool.

This is straightforward enough. But actually filling in these boxes accurately is way harder than it looks. For the diagram to work, it has to be as close to the truth as possible, and to get there, we have to lift up the hood of our subconscious and head down. Let’s start with the Want Box.

Deep Analysis, Part 1: Your Want Box

The hard thing about the Want Box is that you want a bunch of different things—or, rather, there are a bunch of different sides of you, and each of them wants—and fears—its own stuff. And since some motivations have conflicting interests with others, you cannot, by definition, have everything you want. Going for one thing you want means, by definition, not going for others, and sometimes, it’ll specifically mean going directly against others. The Want Box is a game of compromise.

The Yearning Octopus

To do a proper Want Box audit, you need to think about what you yearn for in a career and then unpack the shit out of it. Luckily, we have someone here who can help us. The Yearning Octopus.

We each have our own personal Yearning Octopus5 in our heads. The particulars of each person’s Yearning Octopus will vary, but people also aren’t all that different from each other, and I bet many of us feel very similar yearnings and fears (especially given that I find that Wait But Why readers tend to have a lot in common).

The first thing to think about is that there are totally distinct yearning worlds—each living on one tentacle. These tentacles often do not get along with each other.

It gets worse. Each tentacle is made up of a bunch of different individual yearnings and their accompanying fears—and these often massively conflict with each other too.

Let’s take a closer look at each tentacle to see what’s going on.

The Personal Yearnings tentacle is probably the hardest one to generalize here—it’s pretty particular to each of us. It’s a reflection of our specific personality and our values, and it bears the burden of probably the most complex and challenging human need: fulfillment. It’s also in the shit dealing with not only our current selves, but a bunch of our past selves too. The dreams of 7-year-old you and the idealized identity of 12-year-old you and the secret hopes of 17-year-old you and the evolving passions of your current self are all somewhere on the personal tentacle, each throwing their own little fit about getting what they want, and each fully ready to make you feel horrible about yourself with their disappointment and disgust if you fail them. On top of that, your fear of death sometimes emerges on the personal tentacle, all needy about you leaving your mark and achieving greatness and all that. The personal tentacle is why you don’t find very many billionaires content to spend the rest of their life sipping cocktails on the beach—it’s a highly needy tentacle.

And yet, the personal tentacle is also one that often ends up somewhat neglected. Because in many cases, it’s the ickiest set of yearnings to really go for; because the fears of this tentacle aren’t scary in an immediate way—they creep in out of the background over time; and because the personal tentacle is always at risk of getting bowled over early in your career by the powerful animal emotions of the other tentacles. This neglect can leave a person with major regrets later on once the dust settles. An unfulfilled Personal Yearnings tentacle is often the explanation, for example, behind a very successful, very unhappy person—who may believe they got successful in the wrong field.

The Social Yearnings tentacle is probably our most primitive, animal side, with its core drive stemming back to our tribal evolutionary past. On the tentacle are a number of odd creatures.

As we’ve discussed before on this blog, we all have a Social Survival Mammoth living in our heads who’s earth-shatteringly obsessed with what other people think of us. This means he craves acceptance and inclusion and being well-liked, while likewise being petrified of embarrassment, negative judgment, and disapproval. He really really really wants to be in the in-group and he really really really doesn’t want to be in the outgroup. He’s quite cute though.

Then there’s your ego, who’s a similar character but even more needy. Your ego doesn’t just want to be accepted; it wants to be admired, desired, and fawned upon—ideally, on a mass scale. More upsetting to it than being disliked is being ignored. It wants to be relevant and important and widely known.

There are other characters milling about as well. Somewhere else on the social tentacle is a little judge with a little gavel who gets very butthurt if it thinks people aren’t judging you fairly—if you’re not appropriately appreciated. It’s very important to the judge that people are aware of exactly how smart and talented you think you are. The judge is also big on holding grudges—which is the reason a lot of people are driven more than anything by a desire to show that person or those people who never believed in them.

Finally, some of us may find a loving little dog on our social tentacle who wants more than anything in the world to please its owner, and who just cannot bear the thought of disappointing them. The one problem with this adorable creature is that its owner isn’t you. It’s a person with so much psychological power over you that, if you’re not careful, you may dedicate your whole career to trying to please them and make them proud. (It’s probably a parent.)

The Lifestyle Yearnings tentacle mostly just wants Tuesday to be a good day. But like, a really pleasant, enjoyable day—with plenty of free time and self-care and relaxation and luxuries.

It’s also concerned with your life in the big picture being as great as possible—as far as your lifestyle tentacle is concerned, you should be able to do what you want to do in life, when and how you want to do it, with the people you like most. Life should be full of fun times and rich experiences, but it should also roll by smoothly, without too much hard work and as few bumps in the road as possible.

The issue is, even if you place a high priority on your lifestyle yearnings, it’s pretty difficult to keep the whole tentacle happy at the same time. The part of the tentacle that just wants to sit around and relax will hold you back from sweating to build the kind of career that offers long-term flexibility and the kind of wealth that can make life luxurious and cushy and full of toys. The part of the tentacle that only feels comfortable when the future feels predictable will reject the exact kinds of paths that may generate the long-term freedom another part of the tentacle longs for. The side of you that wants a stress-free life doesn’t get along very well with the side of you that thirsts to be hang gliding off a cliff in Namibia like Richard Branson.

The Moral Yearnings tentacle thinks the rest of the tentacles of your Yearning Octopus are a real pack of dicks—each one more self-involved and self-indulgent than the next. The parts of you on the moral tentacle look around and see a big world that needs so much fixing; they see billions of people no less worthy than you of a good life who just happened to be born into inferior circumstances; they see an uncertain future ahead that hangs in the balance between utopia and dystopia for life on Earth—a future we can actually push in the right direction if we could only get our other tentacles out of our way. While the other tentacles fantasize about what you would do with your life if you had a billion dollars in the bank, the moral tentacle fantasizes about the kind of impact you could make if you had a billion dollars to deploy.

Needless to say, the other tentacles of your Yearning Octopus find the moral tentacle to be insufferable. They also can’t begin to understand philanthropy for philanthropy’s sake—they think, “Other people aren’t me, so why would I spend my time and energy working to help them?”—but they can understand philanthropy for their own motive’s sake. While the moral and lifestyle tentacles tend to be in direct conflict, others may sometimes find common ground—the social tentacle can get very into philanthropy if it’ll happen to win you respect and admiration from a highly regarded social group, and some people’s personal tentacle may find the meaning or self-worth it so craves in a philanthropic endeavor.

That’s why, when you do something philanthropic—or anything altruistic, really—there are a few separate things going on in your head. The part of you determined to get proper public credit for the deed lives on your social tentacle; the part of you that thinks “God I’m a good person” lives on your personal tentacle; and the part of you that really loves seeing the person or group you helped be better off lives on your moral tentacle. Likewise, not doing anything for others can hurt you on multiple tentacles—the moral tentacle because it feels guilty and sad, the social tentacle because this may cause others to judge you as a selfish or greedy person, and the personal tentacle because it may lower your self-esteem.

Your Practical Yearnings tentacle thinks all of this is fine and great—but it would also like to point out that it’s March 31st and your rent is due tomorrow, and the funny thing about that is that it logged into your bank account and saw that the number of dollars in it is actually less than the number of dollars that your landlord will need from you sometime in the next 34 hours. And yeah it knows that you deposited that check on Thursday and that it’s supposed to clear tomorrow morning, but your practical tentacle also could have sworn that just last month, all the tentacles promised that they’d make some sacrifices in order to build up at least a little bank account cushion so that simply paying the rent wouldn’t have to be really fucking stressful every month. Your practical tentacle also can’t help but notice that your social tentacle offered to buy a round of drinks for all nine people you went to the bar with last Saturday so those people would think of you as a classy, generous person, and that your lifestyle tentacle chose to rent what sure seems like a pretty nice-ass apartment for someone now living check to check, and that the updates have gotten real quiet from your friend about that bagel delivery service he started six months ago that your moral tentacle happily invested $2,500 in to help it get off the ground, and oh also that meanwhile your personal tentacle has everyone sweating their dick off working at two comedy-writing internships simultaneously that somehow manage to bring in less money combined than you made dressing up as an Egyptian enchantress to wait tables at Jekyll & Hyde sophomore year of college.

At its basic level, your practical tentacle wants to make sure you can eat food and wear clothes and buy the medicine you need and not live outside. It doesn’t really care how these things happen—it just wants them to happen. But then everyone else on the octopus makes your practical tentacle’s life super hard by being fucky about things. Every time your income goes up, your lifestyle tentacle decides to raise the bar on what it wants and expects, leaving your practical tentacle continually in the shit trying to cover it all so you don’t have to run up your credit card debt. Your personal tentacle has all of these weird needs that take up a lot of time and more often than not aren’t exactly big money-makers. And while your practical tentacle would be totally down to just ask your rich uncle for money to help out, your social tentacle outlawed asking others for money because “it’s not a good look,” with your personal tentacle chiming in that “yeah, we’re better than that.”

So that’s the situation. You’ve got this Yearning Octopus in your head with five tentacles (or however many yours has), each with their own agenda, that often conflict with each other. Then there are the distinct individual yearnings on each tentacle, often in conflict amongst themselves. And if that weren’t enough, you sometimes have furious internal conflict inside a single yearning. Like when your desire to pursue your passion can’t figure out what it’s most passionate about.

Or when you want so badly to be respected, but then you remember that a career that wins the undying respect of one segment of society will always receive shrugs from other segments and even contemptuous eye rolls from other segments still.

Or when you decide to satisfy your urge to help others, before realizing that the part of you that wants to dedicate your life to helping to mitigate humanity’s greatest existential risks has palpable disdain for the part of you that would rather make a tangible positive impact on your local community—while the part of you that can’t stand the thought of the millions of today’s humans without access to clean water finds both of those other yearnings to be pretty cold and heartless.

So yeah, your Yearning Octopus is complicated. And no human in history has ever satisfied their entire octopus—that’s why you’ll never find it fully smiling. Human yearning is a game of choices and sacrifices and compromise.

Dissecting the Octopus

With that in mind, let’s return to your Want Box. When we think about our career goals and fears and hopes and dreams, our consciousness is just accessing the net output of the Yearning Octopus—which is usually made up of its loudest voices. Only by digging into our mind’s subconscious can we see what’s really going on.6

The cool thing is that we all have the ability to do that. The stuff in your subconscious is like stuff in the basement of a house. It’s not off-limits to us—it’s just in the basement. We can go look at it anytime—we just have to A) remember that the house has a basement, and B) actually spend the time and energy to go down there, even though going down there might suck.

So let’s head to the basement of your mind to look for the octopus. Unless you’re one of those people who’s really practiced at analyzing your subconscious, it might be dark in the basement, making it hard to see your octopus. The way to start turning the lights on is by identifying what your conscious mind currently knows about your yearnings and fears, and then unpacking it.

Like if there’s a certain career path that sounds fantastic to you, unpack that. Which tentacles in particular are yearning for that career—and which specific parts of those tentacles?

If you’re not currently working towards that career you supposedly yearn for, try to figure out why not. If you think it’s because you’re afraid of failing, unpack that. Fear of failure can emerge from any of the tentacles, so that’s not a specific enough analysis. You want to find the specific source of the fear. Is it a social tentacle fear of embarrassment, or of being judged by others as not that smart, or of appearing to be not that successful to your romantic interests? Is it a personal tentacle fear of damaging your own self-image—of confirming a suspicion about yourself that haunts you? Is it a lifestyle tentacle fear of having to downgrade your living situation, or of bringing stress and instability into a currently predictable life? Or maybe that fear of a living situation downgrade isn’t actually emerging from your lifestyle tentacle, but more so from your social tentacle—in other words, is it possible you’re indifferent about the apartment change itself but super concerned about the message a lifestyle downgrade sends to your friends and family? Or are there financial commitments you simply cannot back out of at the moment, and your practical tentacle is in a genuine panic about how you’ll make ends meet should this career switch take longer than expected to work out, or not work out at all? Or are a few of these combining together to generate your fear of making the leap?

Perhaps you don’t really think it’s fear of failure that’s stopping you, but something else. Maybe it’s a dread of the change in identity—both internally and externally—that inevitably accompanies a career move like this. Maybe it’s the heavy weight of inertia—an intense resistance to change—that seems to exist in and of itself and overpowers all of your other yearnings. In either case, you’d want to unpack the feeling and ask yourself exactly which tentacles are so opposed to an identity shift, or so driven by inertia.

Maybe you pine to be rich. You fantasize about a life where you make $1.2 million a year, and you feel a tremendous drive to make it happen. All five tentacles can feel a desire for wealth under certain circumstances, each for their own reasons. Unpack it.

As you unpack an inner drive to make money, maybe you discover that at its core, the drive is more for a sense of security than for vast wealth. That can be unpacked too. A yearning for security at its simplest is just your practical tentacle doing what your practical tentacle does. But maybe it’s not actually basic security you want as much as a guarantee of a certain level of fanciness demanded by your lifestyle or social tentacle. Or perhaps what you really want is a level of security so over-the-top secure it can no longer be called a security yearning—instead, it may be an impulse by the emotional well-being section of your lifestyle tentacle to alleviate a compulsive financial stress you were raised to forever feel, almost regardless of your actual financial situation.

The answers to all of these questions lie somewhere on the tentacles of your Yearning Octopus. And by asking questions like these and digging deep enough to identify the true roots of your various yearnings, you start to turn on the basement light and acquaint yourself with your octopus in all its complexity.

You’ll also come to understand which of your inner yearnings seem to speak the loudest in your mind and carry the most pull in your decision-making processes. Pretty quickly, a yearning hierarchy will begin to reveal itself. You’ll identify yearnings that speak loudly and get their way; yearnings that cry at the top of their lungs but get continually elbowed out of the way by higher-prioritized parts of the octopus; yearnings that seem resigned to their low-status positions in the hierarchy.

Searching for Imposters

We’re making good progress—but we’re just getting started. Once you have a reasonably clear picture of your Yearning Octopus, you can start doing the real work—work that takes place another level down in your subconscious, in the basement of the basement. Here, you can set up a little interrogation room and one by one, bring each yearning down into it for a cross-examination.

You’ll start by asking each yearning: how did you end up here, and why are you the way you are? Desires, beliefs, values, and fears don’t materialize out of nowhere. They’re either developed over time by our internal consciousness as observations and life experience pour in, or they’re implanted in us from the outside, by someone else. In other words, they’re the product of either you the chef or you the cook.

So the goal here in your creepy interrogation room is to tug on the faces of each of your yearnings to find out if it’s authentically you, or if it’s someone else disguised as you.

You can pull on a yearning’s face by playing the Why Game. You’ll ask your initial Why—Why is this something I want?—and get to some kind of Because. Then you’ll keep going. Why did that particular Because lead you to want what you now want? And when did that particular Because gain so much gravity with you? You’ll get to a deeper Because behind the Because. And if you continue with this, you’ll usually discover one of three things:

1) You’ll trace the Why back to its origin and reveal a long chain of authentic evolution that developed through deep independent thought. You’ll pull on their face and confirm that the skin is real.

2) You’ll trace the Why back to an original Because that someone else installed in you—I guess the only reason I actually have this value is because my mom kind of forced it on me—and you realize that you never really thought to consider whether you actually independently agree with it. You never stopped to ask yourself whether your own accumulated wisdom actually justifies the level of conviction you feel about that core belief. In a case like this, the yearning is revealed to be an imposter pretending to be an authentic yearning of yours. You pull on its face and it’s a mask that comes off, exposing the yearning’s original installer underneath.

3) You’ll trace the Why back and back and get kind of lost in a haze of “I guess I just know this because it’s true!” This could be an authentic you thing, or just another version of #2, in an instance where you can’t recall the moment this feeling was installed in you. Somewhere deep in you, you’ll have a hunch about which it is.

In a #1 scenario, you can be proud that you developed that part of you like a chef. It’s an authentic and hard-earned feeling or value.

In a #2 or maybe #3 scenario, you’ve discovered that you’ve been duped. You’ve let someone else sneak onto your Yearning Octopus while you weren’t looking. When it comes to that particular belief of yours, you’re a cook following someone else’s recipe—an obedient robot reciting desires and fears out of someone else’s brain.

There’s a chance you’re an unusually wise person whose examination reveals an octopus developed mostly by you and kept readily up to date. More likely, you’re like me and most of my friends—your interrogation room reveals some definite imposters, or at least a lot of ambiguity. Like, underneath one mask, you’ll find your mom.

You’ll pull off others to reveal the values and judgments of broader conventional wisdom, or the viewpoints of your more immediate community, or what’s considered cool by the dominant culture of your generation or the immediate culture within your closest group of friends.

Sometimes you’ll get to the end of a Why-Because pathway only to find the philosophy in a famous novel, or something a celebrity hero of yours once said in an interview, or a strong opinion one of your professors always repeated.

You might even find that some of your yearnings and fears were written by you…when you were seven years old. Like a childhood dream that was etched into the back of your consciousness as the thing you believe you really want, when you’re being truly honest.

The interrogation room probably won’t be that fun a time. But it’s time well spent—because you’re not your 7-year-old self, just like you’re not your parents or your friends or your generation or your society or your heroes or your past decisions or your recent circumstances. You’re Current-Age You—the only person, and the only version of yourself, who is actually qualified to want and not want the things you want and don’t want.

To be clear, this isn’t to say that it’s wrong to live by the words of a wise parent or a famous philosopher or friends you respect or the convictions of a younger you. Humble people are by definition influence-able—influences are an important and inevitable part of who each of us is. The key distinction is this:

Do you treat the words of your external influences as information, held and considered by an authentic inner you, that you’ve carefully decided to embrace? Or are your influences themselves actually in your brain, masquerading as inner you?

Do you want the same thing someone else you know wants because you heard them talk about it, you thought about it alongside your own life experience, and you eventually decided that, for now, you agree? Or because you heard someone talk about what they want or fear, and you thought, “I don’t know shit and that person does, so if they say X is true, I’m sure they’re right”—and then you etched those ideas into your mind, never again feeling the need to question them?

The former is what chefs do. The latter is what you do when you’re being an obedient robot. And a robot is what you become when at some point you get the idea in your head that someone else is more qualified to be you than you are.

The good news is that all humans make this mistake—and you can fix it. Just like your subconscious is right there for viewing if you want to view it—it’s also there for changing and updating and rewriting. It’s your head—you’re allowed to do with it what you want.

So it’s time for some evictions. Masked imposters have to go. Even mom and dad.

At the end of this, your octopus may look a little barren, leaving you feeling a little like you don’t know who you even are anymore. We usually think of this as a bad feeling, or even an existential crisis, but it actually means you’re doing better than most people.

The drop from naive over-confidence to wise, realistic humility never feels good, but pausing the roller coaster while it’s still on that first cliff and avoiding the pain—which turns out to be a lot of people’s move—isn’t a great strategy. Wisdom isn’t correlated with knowledge, it’s correlated with being in touch with reality—it’s not how far to the right you are on the graph, it’s how close you are to the orange line. Wisdom hurts at first, but it’s the only place where actual growth happens. The irony is that the cliff-pausers of the world like to make the wiser, braver valley-dwellers or continual-climbers feel bad about themselves—because they fundamentally don’t get how knowing yourself works. They haven’t reached that stage yet.

Getting to know your real self is super hard and never complete. But if you’ve tumbled off the cliff, you’ve gone through a key rite of passage and progress is now possible. As you climb up the orange line, you’ll slowly but surely begin to repopulate your Yearning Octopus with your real self.

At the moment, it probably won’t be obvious what those missing yearnings of yours are exactly—because they’re on an even deeper floor of your subconscious. They’re in the basement of the basement of the basement—in a place called Denial Prison.

Denial Prison

Our brain’s Denial Prison is a place most of us don’t even know is there—it’s where we

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