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, 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.

I want to make a slightly different observation. I have no problem with our “brightest minds” wanting to work at and make (a lot of) money in finance, consulting, law, tech, etc. And in any case, many have successful and fulfilling careers there. One person might be passionate about climate change, while someone else might be passionate about making money.¹ And depending on what you want out of life, you’ll probably be guided towards taking up a very limited set of career paths, especially if you want to live in a certain city, afford a certain lifestyle, provide for your parents, and send your children to certain schools.² These are all legitimate reasons to want to make a lot of money. My sadness is with the people who could have created a marquee institution, but instead went to go work for one.

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? Of course, our degree of interest working in X industry is endogenous to the level of pay we can expect to receive, but is there a durable, independent desire to work in X industry? We can trade off passion for increased income, but the exchange rate between these is probably sublinear, so we overweight the value of money vis-à-vis passion and end up unhappy. To be clear, some people genuinely light up talking about debt covenants and leverage multiples—Graham Weaver describes meeting exactly such a person, and realising that anyone with that kind of fire would simply crush him. He was living his dream while Weaver was just going through the motions.³ Those people are not who this essay is about. They have found their thing, and they should do it. The question is whether you have that fire, or whether you are borrowing someone else’s.

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 ambition. You can point to the difficulty of breaking in, the intelligent colleagues, the interesting work, which is enough to quiet the part of you that really knows two things: 1) they’re paying you the absolute minimum they can to keep you and 2) the difficulty of getting in is not the same as 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 are who can see how AI is developing.

A few things strike me about this. First, figuring out what you want your purpose to be should be analytically prior to thinking about what career you want. 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 are passionate about. Instead, often I see what career we pursue flows from what we think is most prestigious. Given that your career is the single largest allocation of time and energy, 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 IB 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.

Similar ideas are presented in Good to Great, where Jim Collins 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, 2) something we can be the best in the world at, and 3) that has a clear economic driver. This requires a level of self-reflection and candor that most people—including smart, reflective people—find difficult to do.

I had a longer conversation with the founder of a successful hedge fund, who gave me some sobering 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 this around me every day. A friend of mine is going to work for a boutique investment bank. But when 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 interesting⁴, but this seems like a stretch. Now, maybe you want to work in private equity, and, recruiting being what it is, you need to do IB first, and so you don’t really care about it insofar as it’s just a stepping stone to PE. Fair enough. But why PE? Better pay? More prestige? At some point, you’ll have climbed to the top of the ladder and will need to ask yourself if you are fulfilled and 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. The roommate won’t burn down your apartment, but he also makes it very hard to leave.

It’s worth pointing out this is not an individual phenomenon. I had a long conversation with university leadership, and we found ourselves circling around the same observation: year after year, more students seem to be recruiting for safe and conventional paths. The trend is striking, and they asked me if our admissions process needs to change because we’re selecting for the wrong kind of 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. They learn about lionised, high-paying careers younger than ever—through 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. If the university wants to correct this, I’m not entirely sure what that would look like. It also bleeds into what students see college as. There is a huge amount of apathy—or at least the performance of it—about the world, and the university starts to feel less like a place to learn and more like a very expensive credential factory. I think part of the self-censorship that occurs at places like Stanford is a consequence of 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? Finally, elite universities are attended by students who want prestige, and it seems only natural they keep chasing it once they arrive.

II. Greatness

Can all companies be great? I take a more pessimistic view than Collins probably does. Can all people be great? No, I don’t think everyone has the capacity to be great. 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 if that is true. 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.

If we accept that there really aren’t that many people with the capacity to be prime movers⁵, then the critique so many articles forward seems to carry less weight. I suppose the crux of the issue is with the (few) people I know who seem to have a capacity for greatness—to change the world, to advance the human project—are casting it aside to pursue careers which are lower risk, higher paying, and usually more “prestigious.” To give you an example of this, 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, or hedge fund. 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. In any case, we can guess what he will probably do in the name of optionality.

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. I also have a desire to be great.⁶ I can’t afford to let the wind take me. Some of it comes from conversations with those who are much more fulfilled and successful than I am.

I am living through one of the most significant technological transitions in recent history, and the opportunity cost of defaulting to a conventional path feels uniquely high. 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?