Lying to Ourselves

Preface

This is more of an exercise in thinking through observations and conversations I’ve had. I’m not really trying to persuade you of anything, and I think much of what I have to say here only really applies to a very, very small group of people. People who have the capacity to be great and do not other considerations preventing them from pursuing it. There are many reasons why it might not be appropriate or prudent for you to take on large amounts of risk, even if you have a large risk appetite.

I. Lies

I have read the same article about how our “brightest minds” are wasting their talent doing finance, consulting, law, big tech, or some other industry at least a dozen times over the past five years. Each time, the urgency is more emphatic: “The planet is hotter, the strongmen are more confident, and the threat of runaway AI looms larger…[which] demand exceptional minds now.”¹

I want to make a slightly different observation. I have no problem with our “brightest minds” wanting to work and make (a lot of) money in finance, consulting, law, tech, etc. Many will have successful and fulfilling careers in those fields. Some people genuinely light up talking about debt covenants and leverage multiples.² Plus there are many legitimate reasons to want a high-paying job: you want to live in a London or a San Francisco or a New York, you want to have a family, you want to provide for your parents, and so on. Great. I’m interested in the people who have the capacity to create something great, but instead are being absorbed into existing institutions.³

Two questions are worth asking.

The first question: why are you interested in working X industry? Obviously our degree of interest working in X industry is endogenous to how much it pays—there probably isn’t a clean separation—but is there a durable, independent desire to do the work? We trade off passion for income all the time, but the exchange rate is probably sublinear: we overweight the value of money vis-à-vis passion, and end up unhappy.

One way to get out of this is to claim no trade off exists. Here’s an example from a friend who’s going to work for a boutique investment bank. I asked if she’d still do her job for the prestige, pay, and exit opportunities of a high school teacher. She answered that she would because she “finds M&A very interesting.” I don’t doubt that M&A can be very interesting⁴, but this seems like a stretch. And if you say: well, I don’t really care about IB, it’s just a stepping stone to what I actually want to do, which is X. But why X? Better pay? More prestige? Something else? As Weaver notes: “Life is suffering. So figure out something worth suffering for.”

The second question: are you exhausting your capacity for greatness, or are you being pushed to feel that way? I think the recruiting process for the “Bermuda Triangle of Talent” is extraordinarily good at making the conventional path feel like it can exhaust the entire extent of your living ambition. Firms love to mention their internship acceptance rate, where their employees went to school, the awards they’ve won, and so on, which simulates a sense of exclusivity that, once you’re inside, probably dissolves into something pretty mundane.⁵ You can point to the intelligent colleagues, the interesting work, which might be enough to quiet the part of you that knows they’re probably paying you the minimum they can to keep you there.

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Recently, I met with the founder of a famous investment firm. A few ideas from our conversation that I want to repeat here:

Risk is like a roommate. If you keep an eye on him all day, nothing bad will happen, but you will also be stuck inside all day. If you are out living your life, he might burn the place down. You need to decide what level of oversight you want over Risk; Your career is the most important investment decision you will make—think carefully about it; Look to your peers at Stanford—what are you better at than all of them? You need to figure out what you are exceptional at and love doing; You need to get the major trend right—in his case he was lucky, because the alternative asset space writ large kept growing; You need to get into the right neighbourhood—maybe you want to go work for OpenAI or Anthropic, because that is where the few thousand people in the world who can see how AI is developing are.

Two things to point out. First, figuring out your purpose should be analytically prior to thinking about your career. The career you pursue should flow from what you think you have the potential to be the best in the world at and what you love doing. Instead, I usually see the career flow from what is thought to be the most prestigious. Given that your career is the single largest allocation of time and energy you will make, we probably spend less time thinking about it than we should. I am certainly a victim of not dedicating enough serious thought. Part of this is manufactured as a consequence of extremely early recruiting cycles that funnel you into preparing and applying because of FOMO and to avoid uncertainity. By the time you’ve just settled into college and finished your freshman year, you must immediately make the decision to recruit for finance or not. Not much time for thinking.⁶ Second, the assumption is that the conventional path for twenty-somethings is the safe one. No one will tell you you’re making a mistake working for a Goldman or a McKinsey. But staying inside all day to watch your roommate is its own kind of cost.

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I had a longer conversation with the founder of a hedge fund, who gave me two important observations. First:

Many of his friends began a career path that they were not honest with themselves about why they were pursuing it. Then they lied to themselves about when they would leave and do what they really wanted. Now, nearing the tail end of their careers, they are financially successful but not particularly happy.

Second observation:

Many of his friends started out in a job they didn’t care about because they wanted optionality. But they ended up lying to themselves about when they would leave and when they would do what they really wanted to do. They usually didn’t end up exercising their optionality because of golden handcuffs, lifestyle creep, and so on.

We are not infinite beings, so we cannot have infinite shots on the goal. Taking a punt becomes incrementally harder as you form more permanent relationships, and have more obligations. Simultaneously, you have increasing opportunity costs of leaving and more generous incentive packages that encourage you to stay. Plus the sheer weight of having been somewhere long enough that leaving starts to feel like its own kind of death.

I had a long conversation with university leadership, and we found ourselves circling around the same observation: in the past five years, more and more students seem to be converging towards conventional paths. The trend seems to be striking enough and they asked me whether the admissions process needs to change because we’re selecting for students that would be better served at a different school.

Maybe. But I also suspect many students are solving for the job they want in high school, and then reward hack their way into a good school. Even if we changed the admission criteria to select for more risk-on types, students would simply change their behaviour to better fit the updated criteria, and then recruit for the same industries regardless. This is an example of a multipolar trap. I’m not sure if universities can correct this. The trend is probably partially culturally driven. In high school, or earlier, students learn about lionised, high-paying careers—think of media like American Psycho, The Wolf of Wall Street, Suits, “I’m looking for a man in finance”, and social media writ large—and then reverse-engineer the path to get there. The result is that university stops being a place to learn and stars being a very expensive credential factory.⁷ It’s also a natural reaction to a more uncertain world.

II. Greatness

Can all people be great? No. By definition, not everyone can be above average. Not everyone can be a MLK, not everyone can be a Steve Jobs, and not everyone can be a Picasso. And it also doesn’t really matter. A fulfilling life is certainly not necessarily contingent on achieving greatness by some external metric. A friend of mine has told me that achieving something great would be, well, great, but if it came at the cost of raising a family or not leaving work by 5pm, then he’s not interested.

There is a passage from Siddhartha that I find myself thinking about more and more. Am I like a falling leaf, that “drifts and turns in the air, flutters, and falls to the ground.” A leaf that is blown about by whichever is strongest: prestige, salary, peer expectations, FOMO, etc.? We should become stars, because stars “travel one defined path: no wind reaches them, they have within themselves a guide and a path.” The Hedgehog framework, it turns out, is a secular description of what it means to have your own guide. Collins and Hesse were describing the same thing.

III. Me

The opportunity cost of defaulting to a conventional path feels uniquely high right now. Staying inside to watch the roommate might be the most expensive decision I could make. So why be a falling leaf when you can be a star?