I. Parables

A. Anna is a graduate student studying p-adic quasicoherent topology. It’s a niche subfield of mathematics where Anna feels comfortable working on neat little problems with the small handful of researchers interested in this topic. Last year, Anna stumbled upon a connection between her pet problem and algebraic matroid theory, solving a big open conjecture in the matroid Langlands program. Initially, she was over the moon about the awards and the Quanta articles, but now that things have returned to normal, her advisor is pressuring her to continue working with the matroid theorists with their massive NSF grants and real-world applications. Anna hasn’t had time to think about p-adic quasicoherent topology in months.

B. Ben is one of the top Tetris players in the world, infamous for his signature move: the reverse double T-spin. Ben spent years perfecting this move, which requires lightning fast reflexes and nerves of steel, and has won dozens of tournaments on its back. Recently, Ben felt like his other Tetris skills needed work and tried to play online without using his signature move, but was greeted by a long string of losses: the Tetris servers kept matching him with the other top players in the world, who absolutely stomped him. Discouraged, Ben gave up on the endeavor and went back to practicing the reverse double T-spin.

C. Clara was just promoted to be the youngest Engineering Director at a mid-sized software startup. She quickly climbed the ranks, thanks to her amazing knowledge of all things object-oriented and her excellent communication skills. These days, she finds her schedule packed with what the company needs: back-to-back high-level strategy meetings preparing for the optics of the next product launch, instead of what she loves: rewriting whole codebases in Haskell++.

D. Deborah started her writing career as a small-time crime novelist, who split her time between a colorful cast of sleuthy protagonists. One day, her spunky children’s character Detective Dolly blew up in popularity due to a Fruit Loops advertising campaign. At the beginning of every month, Deborah tells herself she’s going to finally kill off Dolly and get to work on that grand historical romance she’s been dreaming about. At the end of every month, Deborah’s husband comes home with the mortgage bills for their expensive bayside mansion, paid for with “Dolly money,” and Deborah starts yet another Elementary School Enigma.

E. While checking his email in the wee hours of the morning, Professor Evan Evanson notices an appealing seminar announcement: “A Gentle Introduction to P-adic Quasicoherent Topology (Part the First).” Ever since being exposed to the topic in his undergraduate matroid theory class, Evan has always wanted to learn more. He arrives bright and early on the day of the seminar and finds a prime seat, but as others file into the lecture hall, he’s greeted by a mortifying realization: it’s a graduate student learning seminar, and he’s the only faculty member present. Squeezing in his embarrassment, Evan sits through the talk and learns quite a bit of fascinating new mathematics. For some reason, even though he enjoyed the experience, Evan never comes back for Part the Second.

F. Whenever Frank looks back to his college years, he remembers most fondly the day he was kicked out of the conservative school newspaper for penning a provocative piece about jailing all billionaires. Although he was a mediocre student with a medium-sized drinking problem, on that day Frank felt like a man with principles. A real American patriot in the ranks of Patrick Henry or Thomas Jefferson. After college, Frank met a girl who helped him sort himself out and get sober, and now he’s the proud owner of a small accounting firm and has two beautiful daughters Jenny and Taylor. Yesterday, arsonists set fire to the Planned Parenthood clinic across the street, and his employees have been clamoring for Frank to make a political statement. Frank almost threw caution to the wind and Tweeted #bodilyautonomy from the company account right there, but then the picture on his desk catches his eye: his wife and daughters at Taylor’s elementary school graduation. It’s hard to be a man of principles when you have something to lose.

G. Garrett is a popular radio psychologist who has been pressured by his sponsors into being the face of the yearly Breast Cancer Bike-a-thon. Unfortunately, Garrett has a dark secret: he’s never ridden a bicycle. Too embarrassed to ask anyone for help or even be seen practicing – he is a respected public figure, for god’s sake – Garrett buys a bike and sneaks to an abandoned lot to practice by himself after sunset. He thinks to himself, “how hard can it be?” Garrett shatters his ankle ten minutes into his covert practice session and has to pull out of the event. Fortunately, Garrett’s sponsors find an actual celebrity to fill in for him and breast cancer donations reach record highs.

II. Motivation

What is personal success for?

We say success opens doors. Broadens horizons. Pushes the envelope. Shatters glass ceilings.

Success sets you free.

But what if it doesn’t?

Take a good hard look at the successful people around you. Doctors too busy to see their children on weekdays. Mathematicians too brilliant in one field to switch to another. Businessmen too wealthy to avoid nightly wining and dining. Professional gamers too specialized to learn a new hero. Public figures too popular to change their minds.

Remember that time Michael Jordan took a break from basketball and played professional baseball? They said he would have made an excellent professional player given time. Jordan said baseball was his childhood dream. Even so, in just over a year Jordan was back in basketball. It is hard not to imagine what a baseball player Michael Jordan could have been, had he been less successful going in.

I think it was in college that I first noticed something wasn’t right about this picture. I spent my first semester studying and playing Go for about eight hours a day. I remember setting out a goban on the carpet of my dorm room and studying patterns in the morning as my roommate left for classes; when he returned to the room in the evening, he was surprised to see me still sitting there contemplating the flow of the stones. Because this was not the first or tenth time this had happened, he commented something like, “You must be really smart to not need to study.”

I remember being dumbstruck by that statement. It suggested that my freedom to play board games for eight hours a day was gated by my personal success, and other Harvard students would be able to live like me if only they were smarter. But you know who else can play board games for eight hours a day? Basement-dwelling high school dropouts, who are – for all their unsung virtues – definitely not smarter than Harvard students.

When I entered college, they told me a Harvard education would empower me do anything I want. The world would be my oyster. I took that message to heart in those four years – I fell in love, played every PC game that money could buy, studied programming languages and systems programming, and read more than one Russian novel. When I talked to my peers, however, I was constantly surprised at the overwhelming sameness of their ambitions. Four years later, twenty out of thirty-odd graduating seniors at our House planned to work in finance or consulting.

(Now, it could be that college really empowers these bright young scholars to realize their childhood dreams of arbitraging the yen against the kroner. But this is, as they say in the natural sciences, definitely not the null hypothesis.)

All of this would have made a teenager hate the idea of success altogether. I was not a teenager anymore, so I formulated a slightly more sophisticated answer: Regardless of how successful I become, I resolve to live like a failure.

This is a post about all the forces, real and imagined, that can make success the enemy of personal freedom. As long as these forces exist, and as long as human heart yearns for liberty, few people will ever want wholeheartedly to succeed. Were it not already reality, that is a state of affairs too depressing to contemplate.

(Just to be clear, people are plenty motivated to succeed when basic needs are at stake – to put food on the table, to get laid, to pay for the mortgage. But after those needs get met, success just doesn’t look all that great and only certain sorts of delightful weirdos keep striving. The rest of us mostly just lay back and enjoy the fruits of their labor.)

III. Factorization

I think all of the experiences in Section I can be summed up by the umbrella-term “Sunk Cost Fallacy,” but that theory is a little too low-resolution for my tastes. In this section I identify three main psychological factors of the phenomenon.

1. You rose to meet the challenge. Your peer group rose to meet you.

We are constantly sorted together with people of the same age group, at similar levels of competence, at similar stages in our careers. To keep up with the group, you have to run as fast as you can just to stay in place, as the saying goes. And if you run twice as fast as that, you just end up in a new, even harder-to-impress peer group. When your friends are all level 80, it’s dreadfully difficult to restart at level 1.

Your friends may even be sympathetic, but it rarely helps matters.

Maybe you want to try something totally new, and your friends are too invested in their pet genre to emigrate with you.

Maybe you’re excited to learn a new skill one of your hyper-competent friends is specialized in, and you ask them to coach you. Unfortunately, this turns out to be a massive mistake, because your friend only remembers how she got from level 75 to 80, and sort of assumes everything below is trivial. It’s technically possible to learn area formulas as a special case of integral calculus, but only technically.

Maybe you transition to a new role within the team, you struggle to learn a new set of tricks, and you start hating yourself for not pulling as much weight as you’re used to. You start to see a mix of pity and frustration in your teammates eyes as you drag the whole team down.

2. Yesterday, you were bad at everything, and that really sucked. Today you’re good at one thing, and you’re hanging on for dear life.

It’s hard to move out of your comfort zone when your comfort zone is one hundred square feet on top of Mount Olympus and every cardinal direction points straight off a cliff. Seems like just yesterday you stood at the base of this mountain among the rest of the mortals, craning your neck to get a peek at what it’s like up here.

Kindly god-uncle Zeus calls a special thunderstorm for your arrival. Dionysus pours you a frothy drink and shares a bawdy tale. Hephaestus personally fashions you a blade as a symbol of your newfound status. Aphrodite invites you to her parlor for a night of good old-fashioned philosophy. They all act so welcoming, so natural, so in their element, and you know you’re only up here by a stroke of pure luck.

When Hermes returns the next morning and invites you to fly with him on his winged boots to see the world, you decline graciously. Not because you don’t want to – they’re winged boots! – but because the moment you try anything out of the ordinary you’ll be found out for the impostor that you are and god-uncle Zeus will show you his not-so-kindly side and chain you to a liver-eating eagle or a boulder that only obeys the laws of gravity intermittently.

3. Success gave you something to lose.

They say beware the man with nothing to lose.

I say envy him, because he alone is free.

You fondly recall the good old days of two thousand and two when you could go online and post diatribes against religion as a “militant atheist.” In those days, you had nothing, and you were free. You were unattached. You were intellectually wealthy but financially insolvent. You could see one end of the place you call home from the other.

Now that you’ve made it big, you’d have to carefully position mirrors at the ends of three hallways to see that far. You’re attached to wonderful person(s) of amenable sexual orientation(s). You have a reputation to maintain in the ever-smaller circles that you walk. Children in your community look up to you, or so you tell yourself. And so, even though deep in your heart you still believe that only idiots believe in an old man in the sky your Twitter profile identifies you as “spiritual, yearning, exploring.”

IV. Resolution?

It seems to me we have a problem.

We are not a species known for risk-taking, so human flourishing really depends on the explicit emphasis of exploration and openness to new experience. And yet it seems that the game is set up so that the most successful people are least incentivized to explore further. That all the trying new things and pushing boundaries and calling for revolution is likely to come from those with neither the power to get it done nor the competence to do it correctly.

But it’s not a hopeless case by any means. Many of the most successful people got there precisely by valuing freedom, creativity, and exploration, and still practice these values – so far as they can – within the confines of their walled gardens. We live in an information age where getting good at things is as easy as it’s ever been. And at very least we pay lip service to healthy adages like “Stay hungry, stay foolish.”

But what does one do personally to maintain one’s freedom?

I don’t claim to have a fully general solution to this problem, but here is a rule that’s helped me in the past.

When learning something new, treat yourself like a five-year-old.

If you’ve never spoken a word of Korean in your life, it doesn’t matter if you’re a professor of English Literature. As far as learning Korean goes, you’re a five-year-old. Treat yourself like one. Make yourself a snack for memorizing the vertical vowels. Take a break after reading your first sentence and come back tomorrow. When you’re done for the day, suck your thumb while staring at the first Korean word you’ve ever learned and feel the honest pride well up in your heart.

If you’ve never washed a dish in your life, it doesn’t matter if you’re a professional chef. As far as washing dishes is concerned, you’re a five-year-old. Treat yourself like one. Make yourself a snack for figuring out how to dispense dish soap without getting it everywhere. Take a break after finishing the bowls and come back tomorrow. When you’re all done, take a moment to take in that beautiful empty sink and feel the honest pride well up in your toddler heart.

Do you see how profoundly counterproductive it would be for the Korean learner to beat herself up for not being able to converse fluently with her Asian friends after two weeks? Do you see how completely unkind it would be for the novice dishwasher to call himself a useless piece of shit for not being able to execute the most basic of adult tasks?

Be kind to yourself and adjust your expectations to reality. When learning something new, treat yourself like a five-year-old.