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. 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. This is not an argument for something like “follow your passion and take risks” or “don’t be afraid to chase your dreams.” I’m writing about the people I know with a capacity to be great and change the world who are being absorbed into existing institutions.

I. Lying to Ourselves

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 world has never been hotter, democracy has never been so fragile, people have never been so needy, and so on. This is not going to be like those articles.

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—Graham Weaver describes meeting someone who was so obviously and incandescently on fire about them that Weaver realised he was just going through the motions.¹ There are people who are passionate about making money the way other people are passionate about climate change or healthcare, and there is nothing wrong with this.² Plus there are entirely legitimate reasons to want a high-paying job: you want to live in London or San Francisco or New York, you want to send your children to good schools, you want to provide for your parents.³ All fine. I’m not interested in those people here. I’m interested in the ones who could have created a marquee institution, but went to work for one instead.

Two questions are worth asking.

The first question: are you interested in finance, or does it just pay well? Are you interested in corporate law, or does it just pay well? Obviously our degree of interest working in X industry is endogenous to how much it pays—I’m not going to pretend there is 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, and then we lie to outselves about why.

A friend of mine is going to work for a boutique investment bank. I asked her if she’d still do her job for the prestige, pay, and exit opportunities of a high school teacher. She somehow managed to find it within herself and tell me 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 PE/HF/VC—fine. But why PE/HF/VC? Better pay? More prestige? At some point you’ll have climbed far enough up the ladder and will ask yourself if you’re fulfilled. That question doesn’t go away no matter how long you defer it. As Weaver notes: “Life is suffering. So figure out something worth suffering for.”

The second question: are you exhausting your capacity for greatness, or does it just feel that way? I think the system is extraordinarily good at making the conventional path feel like it exhausts 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 difficulty and exclusivity that, once you’re inside, dissolves into something more mundane. You can point to the intelligent colleagues, the interesting work, which is enough to quiet the part of you that really knows 1) they’re paying you the absolute minimum they can to keep you there and 2) the difficulty of gettin in bears almost no relation to the significance of what you do once you’re there.

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Recently, I met with the founder of a private equity 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; 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 PE, and 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, very often, the career flows from what we think is 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. Second, the assumption is that the conventional path for twenty-somethings is the safe one. There is truth to this: no one will tell you you’re making a mistake working for Goldman or McKinsey. But staying inside all day to watch your roommate is its own kind of cost.

Jim Collins, in Good to Great, introduces the Hedgehog framework to think through how companies can—somewhat unsurprisingly—transform themselves from good to great. It is equally true of people. We should 1) work at something we are passionate about and 2) something we can be the best in the world at. This requires a level of self-reflection and candor that most people—including smart, reflective people—find difficult.

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I had a longer conversation with the founder of a successful 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.

I see the beginning of this story around me every day.

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 a kind of death.

This is not an individual phenomenon. After 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 recruiting for safe and conventional paths. The trend is 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 Stern or a Wharton.

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. I think part of the self-censorship at places like Stanford follows from this: if I don’t stir the pot, I can get my A, meet the GPA cut-off, and recruit for X industry. Why rock the boat?⁵

II. Greatness

Can all people be great? No. By definition, not everyone can be above average. Not everyone can be a visionary, not everyone can be a CEO, 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 measure. 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 leaving work at 5pm, then he isn’t interested. This is completely defensible.

But if we accept that there really aren’t that many people with the capacity to be prime movers⁶, then the critique so many articles forward seems to carry less weight. Realistically, there probably is not some huge loss to the world because many bright people work in finance or law or consulting or tech. The issue is with the few people who have a genuine capacity for greatness casting it aside to pursue careers which are lower risk, higher paying, and more prestigious.

I’ll give you an example. One of my friends is very involved in civics. A decade from now, there are two paths I can see for him. Path 1: he becomes a VP at an investment bank or private equity firm. Path 2: he becomes a national leader in civics and democracy advocacy. Path 2 is more impactful; It is also riskier. Path 1 will pay more; Path 2 is where his passion lies. We can guess what he will probably do.

There is a passage from Siddhartha that I find myself thinking about more and more. Most of us are just like a falling leaf, that “drifts and turns in the air, flutters, and falls to the ground.” The leaf 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

I know I want to take risk. Some of that clarity comes from external constraint: on a visa, the range of career paths that are available to me are much narrower, and that has a focusing effect. Some of it comes from conversations with those who are much more fulfilled and successful than I am, who have said, in different words and at different times, roughly the same thing.

I am living through one of the most significant technological transitions in recent history. 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.

I think shooting, missing, and looking stupid is better than never shooting and wondering what could have been for the rest of your life. Why be a falling leaf when you can be a star?