How to Pick a Career (That Actually Fits You) – Notes and Summary

One-sentence summary: How to Pick a Career is maybe the only sane take on career path choices that I’ve ever read.

Rating: 10/10

Author: Tim Urban

Date Completed: April 2018

Tags: Rationality, Exploration, Experimentation, Knowledge Capital, Self-Knowledge, Decision-Making, Career Strategy, Life Strategy, Frameworks

Hot take: My only gripe with How to Pick a Career is that it arrived when I was 28, not 22.

Big Ideas

Career path-making is a critical skill we don’t learn in school.

• Urban likens childhood and early adulthood to a river that feeds into a pond (college or higher education). You didn’t choose the river, and most ponds are pretty similar.
• But when you start looking around as you near the end of your time in the pond, you’re pretty remarkably real-world skill-less and suddenly at the end of the preset path that was handed down to you by society or your parents or other life influencers.
• On our own, for the first time, we have to make our way through the world. We end up on some sort of life path, which ends up becoming the story of our lives.
• Unfortunately, many of us have regrets when we reach the end of our lives and see that life path stretching backward.
• “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 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.”

Choosing a career path that fits you is one of the few things to absolutely be a Chef about.

• As a reminder, reasoning from first principles = chef behavior. Reasoning by analogy = cook behavior. (Refresher notes here.)
• Those who reason from first principles reason like scientists. They try to puzzle together a whole host of different data points to figure out something that makes sense.
• Those who reason by analogy take something that exists already and tweak it, but mostly leave it the same.
• Being a chef is a lot of work. It doesn’t make sense to be a chef in most areas of life – if something isn’t super fucking important to you, it’s almost always way better to be a cook about it.
• “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.”
• “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.”
• There are four reasons that a career is one of those life-changing things you should be a Chef about:
  • Time – you’ll spend 20%-60% of your “meaningful adult time” working.
  • Quality of life – how you spend your working hours determines the quality of life you have around them. This includes, but isn’t limited to: how much money you’ll have, your flexibility, where you’ll live, what you’ll do when you aren’t working, and what kind of partner you’ll choose.
  • Impact – for most people, their careers are how they make meaning and impact the world around them.
  • Identity – career is, rightly or wrongly, all wrapped up in our sense of identity. When asked what you do, you say “I’m a researcher” rather than “I work in research,” for example. That implies 1) “what you do” is your career and 2) that your identity is inextricably linked with your vocation.

The Yearning Octopus (aka why you’re never fully satisfied)

• If you remember from the Cook and the Chef post, two key components come together to create your career option pool: the Want Box and the Reality Box.
• In the Want Box is a bunch of different stuff because many of us have conflicting desires. We want to save the planet, but we want to make a boatload of cash to pay off our law school loans. We want to build beautiful buildings that will define the New York City skyline for years, but we want to preserve historical buildings at all costs. We want to be artists, but we also want the stability and fulfillment of teaching children. There’s a lot of shit going on.
• With that in mind, we have to break down our wants across a few different categories. Enter the Yearning Octopus:

• Each tentacle represents a specific yearning world, and the tentacles usually do not see eye to eye on things.
• Within each of the tentacles, some sub-yearnings fight for control of the direction of that tentacle. Even these can conflict with each other.

There are five tentacles on this particular octopus:

• Personal – this one is probably the most unique to each individual but is really about fulfillment. Your desire to achieve your potential, create meaning, and do something that fits your identity shows up here. The critical thing to note is that this tentacle is hard to prioritize because it’s so personal and emotionally squishy – so it often gets deprioritized for other tentacles. This causes long-term problems as failures to prioritize this tentacle creep in as regret and unhappiness later in life.
• Social – this is where all of our deep-seated tribal desires crop up: fitting in, getting recognition for your work, and maybe even a little desire for fame.
• Lifestyle – “[This 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.” But it also has a lot of big-picture stuff going on. It wants a lot of flexibility to do what you want when you want, and it also wants your life to unfold easily and smoothly. This tentacle is challenging to keep satisfied all at once – if you, say, want to lay in a hammock all day on a tropical island you own, you need to do quite a lot of time-consuming work to, you know, buy an island. It’s also tough to balance adventure and comfort on this tentacle, but such is life.
• Moral – this tentacle is concerned with doing good things for others and placing their needs above your own. It can sometimes team up with the Social tentacle or the Personal tentacle to get on board with philanthropy. Still, sometimes it’s at odds with all the other you-focused tentacles who think that the Moral tentacle is fucking everything up for the rest of the group.
• Practical – “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.”

Dissecting the octopus

• This is a challenging process and one it’s easy to overlook. But it’s critical to figure out what you want and why you want it.
• Go through your yearning octopus and unpack each of your strongest desires. Spend some time here.
• Is your desire for money really about security rather than Scrooge McDuck-level wealth? Is your desire to be a lawyer your idea or your mom’s?
• There are many levels to this process, but the first is figuring out where your wants are from someone else – like a parent, a mentor, or cultural programming.
• The most challenging part is identifying the desires locked up in what Urban calls “denial prison.” These are things you want but have been talked out of by yourself or others. “Maybe you’ll find a repressed passion to teach. Or a desire to be famous that your particular tribe has shamed you out of. Or a deep love of long blocks of free, open leisure time that your hornier, greedier teenage self kicked downstairs in favor of raging ambition.”

Setting priorities

• Now that we’ve figured out where your yearnings are coming from, we can start to assign them some relative ranks based on how valid we believe they are and how much you want to prioritize them in your career path.
• Your actions reveal your current hierarchy. “You may like to think a desire to do something bold is high up on your hierarchy, but if you’re not currently working on something bold, it reveals that however important boldness is to you, something else – some source of fear or inertia in you – is currently being prioritized above it.”
• If you’re not going for something you have an intense yearning to do, fear is usually the culprit. “If your actions seem beholden to yearnings that you don’t believe you actually care that much about, you’re probably not looking closely enough at your fears.”
• At this stage, you’ll want to reset your hierarchy to align your actions with the essential things in your life.
• “Creating your yearning hierarchy is a give and take between what’s important and what’s you. It’s probably a good goal to give higher priority to your more noble qualities, but it’s okay to throw a bone to some of your not-so-noble sides as well – depending on where you decide to draw the line.”

There are five layers to this hierarchy. Prioritizing yearnings is as much about what to knock down the order as what to keep at the top. Do your best to place each desire on the lowest possible shelf with which you would be happy:

• The non-negotiable bowl contains the one thing you must have in a career at the expense of all other things. This bowl is useless if you put too much stuff in it, so be careful.
• The top shelf will drive most of your career choices, but it’s a necessarily small shelf. Maybe 2-3 things go here, so being judicious is key.
• The middle and bottom shelves are for the rest of the desires you care to indulge at all. The middle is for all the wants you’ll turn to if you’re able to satisfy all your top shelf and non-negotiable desires, but where you’re comfortable missing the mark so long as you don’t directly oppose them. The bottom shelf is all your nice-to-have things – if your career is about meaning and helping people, maybe your bottom shelf contains a desire to get rich.
• The trash can is where you put the desires you want to avoid specifically. If you feel a pull toward money and power for the sake of impressing a childhood bully, that might end up here.

The Reality Box

• The reality box shows you your perception of reality much more than the actual reality of your situation and available options.
• The goal of self-reflection is to closely approximate reality on two vectors:
  • Beliefs about the world
  • Beliefs about your own potential
• Beliefs about the world
  • There are two types of careers in most of our minds:
    • Traditional professions: Doctors, lawyers, Corporate America, etc. There’s a career ladder here, so if you can get on it and start climbing, you’ll probably be totally fine and get a good amount of success and money
    • Wildcards: Creative, entrepreneurial, political, etc. No guarantee of success in these fields, and the rewards aren’t evenly distributed. It’s effectively like buying a scratchy lottery ticket.
    • “These are perfectly reasonable assumptions—if you live in 1952. Your beliefs about the world of careers and about what it takes to succeed need just as thorough an unmasking as your yearnings did—and I suspect that behind most of them, you’ll find big, fat conventional wisdom. You might first pull off the mask of one of your beliefs and find your parents or your friends or your college career coach—but if you keep going and pull on their face, you’ll usually see that it’s also a mask, and conventional wisdom is there hiding behind it. A general conception, a common opinion, an oft-cited statistic—none of which have actually been verified by you, but all of which are treated as gospel by society.”
• Beliefs about our own potential
  • We tend to overrate the impact of innate talent on how people fare in their careers. We also tend to conflate talent with skill level – how hard we’ve worked at something to improve upon it.
  • We understand how traditional careers work – hence the ladder thing – and understand that putting in the time is the key to success. In non-traditional jobs, we do not understand this and assume everyone is successful because of unbelievable talent.
• The (actual) career landscape
  • Nobody knows! Because things are changing rapidly. But if you can get a real glimpse at how things are, you’ll have an advantage over many people who are mainly basing their beliefs on conventional wisdom.
  • There are thousands of career options, ranging from brand new to decades-old – but if you don’t like the options out there and have something else in mind, you’ll be able to create it for yourself, like designing your major in college.
  • Urban sees each career path as a game board. We only have instructions for a handful of these game boards, and even these are outdated.
  • When we consider a career path, we need to figure out the most up-to-date rules – otherwise, we’re never going to be able to assess the chances of success in that game accurately.
  • So when you think about the possible paths your life could take, there’s a lot to be excited about:
    • You have lots of options that fit your strengths.
    • Most people who are trying to make it on those paths are playing with outdated rulebooks.
• Your potential
  • We don’t usually know our strengths very well, nor what strengths are needed to succeed in any given game.
  • At a basic level, your strengths and work to this point determine your starting point, and your definition of success determines where that point is on the path.

• Some stars are super far away; others are pretty easy to attain. Some people start a lot closer to some stars; some start farther away.
• The star is a lot broader than your abilities in the job. The star represents your abilities at the total package of things that go into being great at a job. For example:
  • “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.”

Filling in the Reality Box

• A few things you’ll need:
  • An understanding of the general career landscape
  • Knowing specific game boards – what’s going on with each interesting one?
  • Your starting point – including your current skills, resources, and connections
  • Success point – what would you need to feel happy about having chosen this path?
  • Pace: how quickly could you improve, based on your current pace strengths and your pace of improvement of those strengths (aka the ability to accelerate your progress)
  • Level of persistence or how much time you’ll be willing to put into each of the paths
• For each path, take a look at the length of your path, the pace and persistence required, and figure out if you’ll be able to reach your minimum acceptable success level.
• Most of the time, this is a pretty optimism-inducing experience. If you look hard at the landscape, it’s easy to see how you might end up with more options than you thought you had.
• “Reframing a bunch of career paths in your mind will affect your level of yearning for some of them. One career may seem less appealing after reminding yourself that it will entail thousands of hours of networking or multiple decades of pre-success struggle. Another may seem less daunting after changing your mind about how much luck is actually involved. There will be other career paths you hadn’t considered wanting because you hadn’t considered them as real options, but some deep reflection has opened your mind to them.”

Riding the rollercoaster

• Now it’s time to pick some career possibilities out of the option pool.
• Luckily, careers are no longer 40-year slogs through one career path, but rather dots on a path that you’re trying to connect.
• Thinking of a career as a dot on a path rather than a tunnel will help you:
  • Keep your identity separate from what you’re doing with your career at this moment
  • Avoid analysis paralysis in choosing the right career
  • Change careers if your current one isn’t working, without it feeling like a struggle
• “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).”
• So you can’t figure out what dots will be exciting or valuable to you in the future. You’re not there yet. We must focus on the dot in front of us.
• The side effect of taking it one dot at a time is that it’s way less stressful and way more exciting to plan this way. You’re not choosing the next 40 years of your life – you’re choosing an exciting first date.

Overcoming inertia

• When it comes time to make a career move, it’s hard to keep yourself from procrastinating.
• If you’re having a hard time pulling the trigger, the part of your Yearning Octopus that’s stopping you must currently be ranked higher than the part that needs change.
• When this happens, you need to have a chat with the parts of you that are causing problems. Remind them about how the process works and why you’ve decided to rank them lower in the hierarchy to try something new.
• “The older I get, the clearer it becomes that our internal battle as the kindergarten teachers of our mind is like 97% of life’s struggle. The world is easy—you’re difficult.”

The ultimate goal is contentment, not happiness.

• “The times you feel pure happiness are temporary, drug-induced delusions—like the honeymoon phase of a new relationship or new job or the high following a long-awaited success. Those moments are the perfect golf shots of a mediocre golfer’s outing—they’re awesome, and you should enjoy the shit out of them—but they’re not the new normal, and they never will be.”
• Instead, you want to feel content with your life path – like you’re taking a good swing at an important thing. “Chasing happiness is an amateur move. Feeling contentment in those times when your choices and your circumstances have combined to pull it off, and knowing you have all that you could ever ask for, is for the wise.”
• When you’re content with where you are, you can dig in and enjoy the dot you’re on. This is macro presence – the feeling of being fully present in your own life. “For a while, you can just live.”

Further reading:

How to Pick a Career (That Actually Fits You) – Wait But Why (full article)

80,000 Hours – great career advice and resources

The Barbell Strategy for Starving Artists – The Deep Dish

Optionality – Rich Meadows (author of The Deep Dish)