the lottery of career success: or why you may want to bribe OpenAI

I.

Have you ever thought about paying a company like McKinsey or Google $500,000 to work there? Maybe not, but it’s a bit weird how few people think about doing this, or treat getting a job at one of these employers as akin to winning a lottery ticket. There is a rough heuristic that many people have, rightly or wrongly: that one’s career outcome broadly matches their skill set and hard work — if you work at a prestigious company, you are the kind of person who deserves to work at a prestigious company. But I truly believe that career success is much more random and like a lottery than most people truly internalize.

II.

A big news story in Canada this month is the naming of Connor Teskey, a 38-year-old, as the CEO of Brookfield Asset Management, arguably the most significant Canadian company (for reference, the company Mark Carney worked for before he left to become Prime Minister of Canada).

When you read the profiles on Teskey, you don’t see stories of a wunderkind who dazzled the industry with a unique, unparalleled skill set. Instead, you see stories about how the former CEO, Bruce Flatt, loved him, put him in the right rooms, gave him the right opportunities, and effectively groomed him for the role.

But the defining characteristic of his career trajectory isn’t his raw ability — it is winning the lottery of Bruce Flatt choosing him.

This randomness isn’t an exception. I believe it’s how most career advancement actually works. We tend to view career success as a cumulative measure of ability, a scorecard that updates in real-time based on merit. But in reality, I think careers are defined almost entirely by randomness, legibility, and path dependency.

III.

To understand why, let’s reflect on the NBA.

In professional basketball, a top prospect is measured constantly. They are ranked in high school, scrutinized in the NCAA, and then, once they are in the NBA, every single minute of their work is recorded, quantified, and visible. There are huge incentives for teams to watch, study, and accurately value every player. If a player was hyped in college but fails to perform in the pros, their value drops. If an unknown player starts putting up numbers, their value rises — if you are not in the league, they will find you. The feedback loop is tight and continuous.

The corporate world is not the NBA. This sounds quite obvious when you read it on your screen, but I think it’s the kind of thing that most people don’t fully internalize. You may be the most talented, capable person in a given field, performing well beyond your peers at a certain job, and nobody cares. You may have extraordinary potential, but nobody is trying to or will discover you. The default is that nobody except you will ever know your “true” talent or potential. The corollary of this is that it’s on you to demonstrate this value.

In the corporate world, there is no “game tape.” There is no continuous measurement, no updated ranking, no mechanism that corrects the market when it mislabels you. Future employers cannot watch how you performed in your previous role. They have no incentive to do the deep discovery work required to find hidden gems, and even if they did, the costs are too high.

Imagine an NBA team signing a 32-year-old free agent based solely on the fact that they were drafted 7th overall twelve years ago, with no other information other than “they are still in the NBA now.” That is how corporate hiring often works. It doesn’t matter how good you actually are at basketball at age 32, and it doesn’t really matter how bad the other person is (so long as they aren’t bad enough to get booted from the league). Based on their past pedigree, they will sign the multimillion-dollar contract while you are left at home. And unlike in the NBA, where teams that misjudge talent lose games, most companies don’t need to find the best person — they need someone good enough. The prestige filter gives them that, so nobody has any reason to look deeper. The difference between the person who gets hired and the person, even if marginally better, is typically imperceptible to them. But the downstream difference to each person who doesn’t get chosen for one of these jobs is enormous: one gets the credential, the compounding begins, and their career trajectories can diverge by millions of dollars over a lifetime.

This is what makes career randomness so durable. In most markets, mispricing gets corrected — if a stock is undervalued, someone buys it. But the labour market has no equivalent mechanism, because talent in most fields is so hard to judge, career tenure is so short, and the blunt reality is that most jobs require you to have an existing body of knowledge from working in that kind of environment before — which if you don’t have, you will functionally never be given an opportunity to acquire.

IV.

I have worked three significant jobs before my current one. In each role, I was viewed as an “all-star” employee, empowered to work autonomously on whatever I wanted to work on and handle high-leverage tasks. But despite all that, in getting any subsequent job, my actual performance in the previous role was never a factor. My new employers had no idea I was an all-star. They hired me based on a de novo analysis of how I presented in the interview, the prestige of the names on my resume, and the kinds of tasks I I chose to write on my resume as being responsible for. I should note: all jobs had a robust interview process and take-home assignment. It’s just that those things are pretty poor indicators of ability and future performance and, once again, reflect nothing about how or what I did in my prior job.

Aside from delivering shareholder value and I guess making myself feel proud, there was no career benefit to being excellent in my previous jobs. My actual abilities, measured by my actual track record, were completely invisible to the people making hiring decisions for all my subsequent jobs.

With the exception of a few technical fields like programming or engineering where you can test via Leetcode or coding tests, it is too difficult to measure ability directly during the hiring process for most jobs. Instead, companies hire based primarily on what you did or where you did it in your previous job, which you only could have gotten based on what you did in the job before that. Since companies receive hundreds of applications, and so much of one’s actual work is illegible, hiring for prestigious companies has a strong filter: did this person previously work at a similarly prestigious company? The best predictor of your next job is your last job. The best predictor of your last job was the one before that. Follow the chain back far enough and you usually arrive at something arbitrary.

V.

We often hear about wealthy parents bribing top colleges to admit their children. But something we don’t hear about is parents bribing McKinsey or Google to let their kids work there. Yet working at McKinsey or Google will often define someone’s future career trajectory far more than which university they went to.

I know what you might say: rich people frequently do give prestigious jobs to their kids or offer significant business to a company on the condition they hire their child. Or maybe rich people in fact do bribe companies like McKinsey directly and we just don’t hear about it because they aren’t under regulatory oversight in the same way. But I don’t think most people think of getting a prestigious job as something worth bribing for in the same way they view getting into Harvard.

But consider the logic. If you want to work at Anthropic on their sales, marketing, or legal team, my understanding is that they aren’t that interested in measuring the raw ability of all candidates. They are checking if you previously worked at Stripe or Google. And to get that job at Stripe, you needed to be sorted from a previous job of a similar tier.

This happens because prestige creates a compounding loop. If you work at a place like Stripe, you suddenly know many people who can be a resource for you. They become your referrals at new companies, and because they already met the prestige bar, they will be going to the exact kind of companies you want to work at next. Furthermore, you need to work at these kinds of companies to do the kind of work that future prestigious companies want to see. You can’t demonstrate “Stripe-scale” product management if you are working at a regional bank.

But getting into these companies is often just randomness. You can get in by starting at the beginning of your career and being lucky (or having already been sorted via the American university pipeline). Or you can start in an emerging area (like privacy or AI safety) before it is trendy, and then prestigious companies need to hire people with experience, and there aren’t that many people there. Or you start at a startup that is not prestigious, but over time it grows to be prestigious, retroactively gilding your resume.

This is why, notwithstanding the logistics and ethical issues, theoretically “paying” McKinsey or Google $500,000 for the right to work there for two years would actually be a rational investment for some — likely higher expected value than an MBA. Once you possess the badge of a prestigious firm, you become legible to the entire market. Your future jobs are almost entirely based on your past jobs, compounding over time. It doesn’t matter if you improve; it matters if you remain on the path.

VI.

This path dependency creates a cruel catch-22: if you miss the initial sorting, you are often locked out forever.

As a law student who loved economics, I wanted to work as a competition lawyer, the one area of law that engages with economics. Unfortunately for me, competition law is very prestigious and only practiced at a small number of the very top firms in Canada. This meant I was outcompeted by those with top grades. Because the field was practiced by so few firms, once I missed this initial hiring round in my second year of law school, there was practically no way to get the relevant experience. Those jobs were effectively unavailable to me for the rest of my career, no matter my interest or ability.

But the same randomness that locks people out also creates backdoors.

Right now, as I watch the Winter Olympics, I am struck by how unequal a gold medal may be across different sports, all while retaining the prestige of an Olympic medal. Some sports have millions of kids dedicating their lives to them while others like Skeleton have fewer than 1,000 participants worldwide.

High-status career paths like law, investment banking, and consulting are like Swimming in the Olympics. Everyone knows the rules, and you are fighting against hundreds of thousands of others who have been training for this since they were teenagers.

But there is another category of career success that looks more like Skeleton.

Skeleton is a sport where you ride a small sled down a frozen track face-first. There are only about 18 tracks in the entire world. Nobody grows up dreaming of being a Skeleton champion. But if you happen to live near a track, and you happen to try it, and you possess a baseline level of athleticism (and perhaps critically, have rich parents), you are suddenly competing against a pool of maybe 300 people globally. Or, as is the case more recently, your country is hosting the Winter Olympics, and they pay random athletic people to learn and train in this sport because there is so little competition. Nobody discounts a gold medal because only 300 people play the sport.

In the corporate world, these “Skeleton tracks” are niche departments, like the Risk Management department at Goldman Sachs or the marketing department at McKinsey.

Nobody dreams of being on the Risk Team at Goldman Sachs. It usually happens randomly: you graduate, you need a job, you know someone, you apply on a whim, and you fall into it. But many of these random jobs pay well, still have lots of prestige, and have a lot less competition than the Swimming track (working as an investment banker at GS). Once you are on the track, gravity takes over for the rest of your career. Because there are so few people who work in risk in the big finance world, once you have the experience, you are effectively “in.”

When you meet people in their 40s in senior positions in these roles, it reveals the randomness of it all, because rarely did this person actually have an interest in risk. They randomly got a job in a specific niche in their 20s and just kept going. This describes most people’s careers.

VII.

Another dimension of this is the nature of the superstar and the standout successes. Once you reach a certain level of wealth, status, or success, whether through the Swimming track or the Skeleton track, the rules of the game change.

I often think about Matt Lakeman’s blog post on meaning, where he describes the lives of Arnold Schwarzenegger and Steve Bannon. He cites the incredible, varied things they’ve done, but what stands out to me is that they really only did one thing that mattered. They each did one thing that made them sufficiently connected, desirable, and financially successful to then pursue and succeed in everything else. That one success enabled all the rest.

Consider Elon Musk creating xAI. The company is valued at $200+ billion, not because of any unique labor or insight that went into its founding, but because Elon Musk founded it. If you or I had the exact same thesis, we would have received zero investment and nothing to show for it. But when you are already a “someone,” doing almost anything becomes infinitely easier. Yet when a future biography is written, Musk will get credit for starting another multibillion-dollar company, when really, xAI is just downstream from prior success.

Many people reach a level of “career escape velocity” where they can leverage their existing credentials to achieve 10x (or sometimes far greater) success, none of which would have been possible without the initial position that set everything in motion. A lot of one’s career story is just playing the game until they can get to this point, which once again, often originates from an arbitrary starting point.

VIII.

While there are many brilliant people in NYC, one of the things that stood out most to me since moving here is how incredibly conscientious people are. I’ve met so many people who are so successful, whether in academia, tech, law, finance, politics, or media, who seem utterly non-remarkable and without passion for anything other than success. But you can tell: these people are exceptionally hardworking and dedicated, the kind of people who not only do all the right networking and say all the right things, but have been doing this since they were teenagers. These large-scale hiring processes bias heavily towards conscientiousness — towards those who are comfortable molding their entire personality to fit in, who practice hard to ace the interviews and say all the right buzzwords. And while conscientiousness matters, it’s overvalued once everyone has already been filtered for it. If you find yourself in a room full of people who all got there through these prestige pipelines, you should probably pay the most attention to the least conscientious person in the room — because they must have faced far more adversity to end up there, and possess something rare enough to overcome the bias against them.

In the specific sector I work in (previously law and now tech), I am surprised by how few US companies hire in Canada. The Canadians I know in these fields are typically on par with the Americans, but doing the same work at half the price. This superficially looks like an economic puzzle: with no timezone difference, language barrier, or cultural friction, why would American companies not hire the much cheaper Canadians? I believe the answer brings together everything I’ve touched on in this essay. The reason is legibility. There aren’t enough Canadians with resumes that American hiring algorithms recognize. If an American tech company uses “Previously worked at a company like Amazon” as a filter, a software engineer from RBC, despite being equally talented, does not pass the filter. If Canada wanted to see more of its citizens hired by US companies, the strategy shouldn’t be better education or training. It should be subsidizing large US companies to open offices in Canada, purely to brand candidates as “Amazon Product Managers.” Because once they have the badge, the market will finally see them.

The bottleneck for most people is not talent. It’s getting lucky enough to get the badge, and riding it for the rest of their career.