Notes: How to Pick a Career (That Actually Fits You)

How to Pick a Career (That Actually Fits You)

 Src: https://waitbutwhy.com/2018/04/picking-career.html


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.


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.


The Cook and the Chef—Revisited

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

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


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.


But then there are those parts of life that are really really deeply important. Career-path-carving is definitely one of those really really deeply important things. Let’s spell out the obvious reasons why:


Time: At the moment, a long human life runs at about 750,000 hours.  you’re left with 250,000 “meaningful adult hours.” (Career).


Quality of Life: 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: 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. The kind of impact you end up making is largely within your control


Identity: 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.” 


Your Career Map

Careers I want, which contains all the careers you find desirable.


Careers that are possible, the Reality Box is for the set of all careers that are realistic to potentially achieve


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.

But actually filling in these boxes accurately is way harder than it looks.


Deep Analysis, Part 1: Your Want Box

Personal

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.


Social

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.



Lifestyle

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.



Moral

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


Practical

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.

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


Passion

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.




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

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.

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.

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?

Searching for Imposters

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. In a case like this, the yearning is revealed to be an imposter pretending to be an authentic yearning of yours. 

  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. 

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.

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.

Denial Prison

Our brain’s Denial Prison is a place most of us don’t even know is there—it’s where we put the parts of us we repress and deny.

The authentic yearnings of ours that we’re in touch with—i.e. those that proved to be authentic during interrogation—were easy parts of our true selves to find in our subconscious, lying in plain sight, right below the surface of our consciousness. 

But then there are the parts of you that weren’t living on your octopus where they’re supposed to be—instead, you found an imposter in their place.

If dad has successfully convinced you that you care deeply about having a prestigious career, he probably has also convinced you that the part of you that, deep down, really wants to be a carpenter isn’t really you and isn’t what you really want. At some point during your childhood, he threw your passion for carpentry into a dark, dank Denial Prison cell.

Priority Rankings

It’s important to remember that a ranking of yearnings is also a ranking of fears. The reverse side of each yearning is its accompanying fear of the opposite. The reverse side of your yearning to be admired is a fear of embarrassment. 

With both yearnings and fears in mind, think about what your internal hierarchy might look like, and return that same important question: “Who made this order? Was it really me?”


Five levels:

  1. Non-negotiable bowl
    The NN bowl is for yearnings so important to you that you want to essentially guarantee that they’ll happen—at the expense of all other yearnings, if necessary.
    The bowl is small because it should be used very sparingly—if at all. Like maybe only one thing gets it. Or maybe two or three. Too many things in the NN bowl cancels out its power, making that the same as having nothing in the bowl at all.

  2. Top shelf
    Your group of top shelf yearnings is mostly what will drive your career choices—but top shelf placement should also be doled out sparingly (that’s why it’s not a very large shelf).
    No matter what your hierarchy looks like, some yearnings will be left feeling very unhappy and some fears will feel like they’re being continually assaulted. This is inevitable.

  3. Middle shelf
    The middle shelf is good for those not-so-noble qualities in you that you decide to accept. They deserve some of your attention. And they’ll often demand it—core parts of you won’t go quietly into non-prioritization, and they sometimes can really ruin your life if they’re neglected.

  4. Bottom shelf
    “I know you want these things, but for now, I’ve decided other things are more important. I promise to revisit you a little later,”.
    The more yearnings you can convince to accept a bottom shelf rating, the better the chances your top shelf and NN bowl yearnings have of getting what they want.

  5. Trash can
    A good amount of inner conflict emerges from people’s trash cans, and trash can control is a major component of integrity and inner strength. But like the rest of your hierarchy decisions, your criteria for what qualifies as trash should be derived from your own deep thought, not from what others tell you is and is not trash.

Deep Analysis, Part 2: Your Reality Box

The Want Box deals with what you find desirable. The Reality Box deals with what’s possible.

But when we examined the Want Box, it became clear that it’s not necessarily based on what you actually want—it’s based on what you think you want—what you’re in the habit of wanting.

The Reality Box is the same deal. It doesn’t show you reality, it shows your best crack at what reality might be—your perception of reality.


The Career Landscape

First, there’s the broad landscape—the set of all the jobs someone could possibly have in today’s society.

if there’s an option you want that’s not already out there, you can probably create it for yourself. Pretty stressful, but also incredibly exciting.


There are likely dozens of awesome career paths that beautifully match your natural strengths, and it’s likely that most other people trying to succeed on those paths are playing with an outdated rulebook and strategy guide. If you simply understand what the game board really looks like and play by modern rules, you have a huge advantage.


Your Potential


And this brings us to you and your particular strengths. Not only do we assess our strengths based on the wrong game boards (like in our basketball example)—even when we have the right game board in mind, we’re often bad at identifying the real strengths that that game calls for.

When assessing your chances on a certain career path, the key question is:

With enough time, could you get good enough at this game to potentially reach whatever your definition of success is in that career?


The game boards in less traditional careers often involve many more factors. Reaching the “I want to be a famous actor” star doesn’t simply mean getting as good at acting as Morgan Freeman, it means getting as good at the entire actor game as most movie stars get by the time they break through. Acting ability is only one piece of that puzzle—you also need a knack for getting yourself in front of people with power, a shrewdness for personal branding, an insane amount of optimism, a ridiculous amount of hustle and persistence, etc. If you get good enough at that whole game—every component of it—your chances of becoming an A-list movie star are actually pretty high. That’s what hitting the star means.


Progress = Pace x Persistence.

Your outlook on any career quest depends on A) the pace at which you’ll be able to improve at playing that career’s “game” and B) the amount of time you’re willing to persist in chasing that star. Let’s talk about both of these:

Pace

What makes someone slower or faster at improving at a career game? I’d say it comes down to three factors:


Your level of chefness.

In a world where career games are constantly evolving and morphing, the chef’s tactics can evolve in real time and keep up. Meanwhile, the cook’s recipe just grows more and more outdated—a problem they remain oblivious to. This is why I’m pretty convinced that at least for less traditional careers, your level of chefness is the single most important factor in determining your pace of improvement.


Your work ethic.

Someone who works on their career 60 hours a week, 50 weeks a year, is going to move down the path almost four times faster than someone who works 20 hours a week, 40 weeks a year. Someone who chooses a balanced lifestyle will move slower than a single-minded workaholic. 


Your natural abilities.

Smarter, more talented people will improve at a game at a faster rate than less naturally gifted people. But intelligence and talent are only two types of natural ability that come into play here


Persistence

The more years you’re willing to commit to chasing a star, the farther along the road towards the star you’ll get. A car going 30 mph that quits driving after 15 minutes gets a lot less far than a car that drives 10 mph for two hours.


Your Real Strengths and Weaknesses

Qualities related to persistence, like resilience and determination and patience, should be thought of as promising strengths, while a social tentacle clamoring to appear successful as quickly as possible should be viewed as a bright red flag.

Most importantly, these items shouldn’t be discussed as a snapshot of where they are now, but rather in terms of your potential for improvement in each of them. If you handed 25-year-old Michael Jordan a basketball for the first time, he’d suck. But calling basketball a “weakness” of his would be getting it very wrong. Instead, you’d want to watch him practice over the next six weeks and evaluate the slope of his improvement. 

Filling in the Reality Box

let’s worry about the parts of the Reality Box that might actually end up in your Option Pool

1) The general landscape. Take our best crack at evaluating the world’s current career landscape—the full range of options available (or create-able).

2) Specific game boards. For any careers that sound remotely interesting, ponder what the deal might be with that career’s current game board—the parties involved, the way success seems to be happening for others recently, the most up-to-date rules of the game, the latest new loopholes that are being exploited, etc.

3) Starting point. For those paths, evaluate your starting point, based on your current skills, resources, and connections relevant to that field.

4) Success point. Think about end points and where on each line your star should be placed. Ask yourself what’s the minimum level of success you’d need to achieve in order to feel happy about having chosen that career path.

5) Your pace. Make an initial estimate for what your pace of improvement might be on these various game boards, based on your current pace-related strengths and how much you think you can improve at each of them (in other words, how much your speed might be able to accelerate).

6) Your level of persistence. Evaluate the amount of time you think you’ll be willing to put into each of these respective paths.


Connecting the Dots into the Future

Careers used to be kind of like a 40-year tunnel. You picked your tunnel, and once you were in, that was that. You worked in that profession for 40 years or so before the tunnel spit you out on the other side into your retirement.

When you think of your career as a tunnel, you lose the courage to make a career switch, even when your soul is begging for it. It makes switching careers feel incredibly risky and embarrassing, and it suggests that someone who does so is a failure. It also makes all kinds of multi-faceted, vibrant, mid-career people feel like they’re too old to make a bold switch or start a whole new path afresh.

Reframing your next major career decision as a far lower-stakes choice makes the number of options exciting, not stressful.

Today’s career landscape isn’t a lineup of tunnels, it’s a massive, impossibly complex, rapidly changing science laboratory. Today’s people aren’t synonymous with what they do—they’re impossibly complex, rapidly changing scientists. And today’s career isn’t a tunnel, or a box, or an identity label—it’s a long series of science experiments.

If you look at the biographies of your heroes, you’ll see that their paths look a lot more like a long series of connected dots than a straight and predictable tunnel. If you look at yourself and your friends, you’ll probably see the same trend—according to data, the median time a young person stays in a given job is only 3 years (older people spend a longer time on each dot, but not that much longer—10.4 years on average).


Likewise, you’re limited to focusing mainly on the next dot on your path—because it’s the only dot you can figure out. You don’t have to worry about dot #4 because you can’t anyway—you’re literally not qualified to do so.

By the time dot #4 rolls around, you will have learned stuff about yourself you don’t know now. You’ll also have changed from who you are now, and your Yearning Octopus will reflect those changes.

The fantastic website 80,000 Hours (which exists to help young, talented people work through their career choices) has compiled a lot of data to back this up: data on the fact that you’ll change, that the world will change, and that you’ll only learn with time what you’re actually good at. Popular psychologist Dan Gilbert also eloquently describes just how bad we are at predicting what will make us happy in the future.


Making Your Move

You’ve reflected and reflected and reflected and weighed and measured and predicted and considered. You’ve chosen a dot and drawn an arrow. And now you have to actually make the move.

Your behavior at any given point simply displays the configuration of your octopus. If you’ve decided on a life step and you can’t quite take it, it’s because the parts of you that don’t want to make a move are ranked higher in your subconscious than the parts of you that do.

Your conscious mind may have tried to assign lower shelf ratings to the parts of your octopus that lean towards inertia, but your yearnings have rebelled


Think like a kindergarten teacher. In your class, a faction of the 5-year-olds is rebelling against your wishes. What do you do?

Go talk to the 5-year-olds that are causing the trouble. Remind them about how connecting the dots works and about the chillness of dot #1. You’re the teacher—figure it out.

our internal battle as the kindergarten teachers of our mind is like 97% of life’s struggle. The world is easy—you’re difficult. If you find yourself continually not executing your plans in life and your promises to yourself, you’ve uncovered your new #1 priority—becoming a better kindergarten teacher.

After the Move

First of all, for a while at least, you’ll probably suck at what you’re doing on your new dot. While your wise self will know that’s exactly how it should be, your less wise selves will go into full existential meltdown mode.

The yearnings you didn’t prioritize will get out the guitar and start singing love songs for the greener-seeming grass you deprived them of. It won’t be much fun.

As you get wiser, you’ll learn to view a largely unhappy octopus with acceptance. 

The whining octopus is a reminder of why pure, elated happiness is never a reasonable goal. The times you feel pure happiness are temporary, drug-induced delusions—like the honeymoon phase of a new relationship or new job.

A better goal is contentment: the satisfying feeling that you’re currently taking the best crack you can at a good life path; that what you’re working on might prove to be a piece of an eventual puzzle you can feel really proud of. Chasing happiness is an amateur move.


People talk about being present in the moment, but there’s also the broader concept of macro-presence: feeling broadly present in your own life. If you’re on a career dot that, when you’re being really honest with yourself, feels right, you get to stop thinking and stop planning for a while and just dig in. You’ll come back to the big picture later—for now, you can put the macro picture aside, put your head down, and dedicate all of your energy to the present. For a while, you can just live.


The Next Dot?

At some point, your good feelings about the macro picture may sour. And when they do, you’ll have to get back into analysis mode and figure out what, in particular, is causing the restlessness.

 A mission-changing dot jump may be in order, but depending on which parts of you are asking for it, it may also be the wrong move.

In these moments, it’s important to consider where you tend to be on this spectrum:


The question is whether your impulse to jump missions is the result of genuine evolution or quick-quitter bias.

Have you learned new information about yourself or the world during the trudge that has corrected some off-base initial assumptions? Or maybe something is fundamentally evolving—some blue or yellow loop activity:

If you feel that things have genuinely changed, you may decide to zoom out even further and think about the big red loop, which deals with fundamentally changing your mission:

If a career is like connecting the dots, we should probably rank “getting wise about dot-jumping” pretty high on our to-do list.

The best place to start is by looking at your own past. Studying your own past decisions, with the flashlight of hindsight and accumulated wisdom.


Over the course of your life, your good and bad decisions will collaborate to forge your unique life path. Often on this blog, I’ve written about how irrational our fears can be and how badly they can hold us back. But we should probably embrace the fear of end-of-life regret.


I think end-of-life regrets may simply be your authentic self thinking about the parts of your life you never got to live—the parts of you that someone else kicked down into your subconscious.


My goal for the future isn’t to avoid mistakes, it’s for the mistakes I do make to be my own.

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