I often get asked these questions from young people who are considering going to law school: “Do you use your law degree in what you do? Has it helped you?” These are difficult questions to answer succinctly. It’s impossible for me to say that it doesn’t play into my day-to-day activities because law school and briefly practicing law rewired my brain. I’m more structured and detail-oriented than I would have been. Having gone to law school years ago still impacts my job performance every day. Plus, people tended to accord me some professional respect in my twenties in part because I had a high-value graduate degree. It would be disingenuous not to acknowledge the impact it’s had. On the other hand, it’s not as if I’m editing contracts or figuring out if something is legal on a regular basis. If I were to come across a genuine legal issue I’d call a lawyer who specializes in that sort of thing or look it up online like anyone else. Legal training (and the subsequent indebtedness) would not be my first suggestion to a young person looking to do something enterprising.* I felt I had to unlearn a lot as I embarked down a very different road.

While I enjoy the work because of my love of mathematics, I luckily realized that this career path was simply designed to exploit inefficiencies in markets in order to extract profits from others. This financial realm known as trading is a zero-sum game where for every dollar you make, someone else loses a dollar, and I know I’m not destined to become such an obvious parasite on society. I only aspire to lead a meaningful, impactful life where I can apply my skills as an extremely analytical individual toward the benefit of humanity.

Our culture of achievement has grown to emphasize visions of success that are, for the most part, fairly predictable. Cole skipped a couple of steps. The basic plan is to go to Goldman Sachs, McKinsey, or the like, then maybe to a top-ranked business school, then back to banking, consulting, private equity, hedge funds, or a name-brand tech company. Or maybe go from law school to top firm to partner or in house at an investment firm, and live in New York, San Francisco, Boston, or Washington, DC.* Again, these institutions and roles are necessary, and they’re natural developments in our economy. We need them. But we need people doing other things too. We need people willing to take risks and, yes, to occasionally fail. Like real-world consequences fail. We need people committed over extended periods of time to creating value, no matter how hard that is. We need people who care deeply about the work they’re doing. Imagine someone who you think could stand to take on some risk — someone well educated who would always have something to fall back on, whose family might have some resources so he would be unlikely to starve. And this person would probably be young and free of major life obligations. Someone sort of like . . . Cole. What’s interesting is that many of the people I meet who are young, highly educated, and from good families are among the most risk-averse. They feel like they need to be making progress along a ladder with each passing month or year. Their parents have often set high expectations for them. They measure themselves each period against their peers, who are generally following various well-defined paths.

I had several friends from law school who were very enterprising guys, much more so than the average law student. They each started businesses after practicing law at large firms for multiple years. What kind of businesses did they start? They started boutique law firms. This is completely unsurprising if you think about it. They’d spent years becoming good at delivering legal services. It was a field that they understood and could compete in. Their credentials translated too. People learn from what they’re doing and do it again on their own. It’s not just lawyers; the consulting firm Bain and Company was started by seven former partners and managers from the Boston Consulting Group. Myriad boutique investment banks and hedge funds have spun out of large financial organizations. You can see the same pattern in the startup world. After PayPal was acquired by eBay in 2002, its founders and employees went on to found or cofound LinkedIn (Reid Hoffman), YouTube (Steve Chen, Jawed Karim, and Chad Hurley), Yelp (Russel Simmons and Jeremy Stoppelman), Tesla Motors (Elon Musk), SpaceX (Musk again), Yammer (David Sacks), 500 Startups (Dave McClure), and many other companies. PayPal’s CEO, Peter Thiel, famously made a $500,000 investment in Facebook that grew to over $1 billion. In this sense, PayPal is one of the most prolific companies of recent times. But if you look at any successful growth company you’ll start to see their alumni show up doing parallel things. Former Apple employees founded or cofounded Android, Palm, Nest, and Handspring, companies that revolve around devices. Former Yahoo! employees founded Ycombinator, Cloudera, Hunch.com, AppNexus, Polyvore, and many other web-oriented companies. Organizations give rise to other organizations like themselves.

popular notion out there that ideas change the world. That’s wrong. People change the world. People making commitments and sacrifices and doing something about the forces that are tearing our society apart. Whom do we serve, Humanity or the Market? Are we the opiated

It wasn’t until I got to the law firm that things started hitting me. First, the people around me seemed pretty unhappy. You can go to any corporate law firm and see dozens of people whose satisfaction with their jobs is below average. The work was entirely uninspiring. We were for the most part grease on a wheel, helping shepherd transactions along; it was detail-intensive and often quite dull. Only years later did I realize what our economic purpose was: if a transaction was large enough, you had to pay a team of people to pore over documents into the wee hours to make sure nothing went wrong. I had zero attachment to my clients — not unusual, given that I was the last rung down on the ladder, and most of the time I only had a faint idea of who my clients were. Someone above me at the firm would give me a task, and I’d do it. I also kind of thought that being a corporate lawyer would help me with the ladies. Not so much, just so you know. It was true that I was getting paid a lot for a twenty-four-year-old with almost no experience. I made more than my father, who has a PhD in physics and had generated dozens of patents for IBM over the years. It seemed kind of ridiculous to me; what the heck had I done to deserve that kind of money? As you can tell, not a whole lot. That didn’t keep my colleagues from pitching a fit if the lawyers across the street were making one dollar more than we were. Most worrisome of all, my brain started to rewire itself after only the first few months. I was adapting. I started spotting issues in offering memoranda. My ten-thousand-yard unblinking document review stare got better and better. Holy cow, I thought — if I don’t leave soon, I’m going to become good at this and wind up doing it for a long time. My experience is a tiny data point in a much bigger problem.

Your expenses grow to match your income. As the decades pass and you realize that no, you’re not going to save the world, the money becomes a more and more important part of the justification. And when you have kids, you’re stuck; it’s much easier to deprive yourself of money (and what it buys) than to deprive your children of money. More important, you internalize the rationalizations for the work you are doing. It’s easier to think that underwriting new debt offerings really is saving the world than to think that you are underwriting new debt offerings, because of the money, instead of saving the world. And this goes for many walks of life. It’s easier for college professors to think that, by training the next generation of young minds (or, even more improbably, writing papers on esoteric subjects), they are changing the world than to think that they are teaching and researching instead of changing the world. Sure, there are self-parodying, economically delusional, psychotherapy-needing, despicable people on Wall Street . . . but there are also a lot of people who went there because it was easy and stayed because they decided they couldn’t afford not to and talked themselves into it. A college student asked me at a book talk what I thought about undergraduates who go work on Wall Street. And individually, I have nothing against them, although I do think they should do their best to keep their expenses down so they will be able to switch careers later. But as a system, it’s a bad thing that a small handful of highly profitable firms are able to invest those profits into skimming off some of the top students at American universities — universities that, even if nominally private, are partially funded by taxpayer money in the form of research grants and federal subsidies for student loans — and absorbing them into the banking-consulting-lawyering Borg.7

When I applied to college in 1992, my parents were pumped that I got into Stanford and Brown, schools that had acceptance rates of 21 and 23 percent, respectively, at the time. Today, the acceptance rates at those schools are only 4.8 percent and 9.3 percent. What was once very difficult now requires planning and cultivation from birth.

Works in ChatGPT, Claude, or Any AI

Add semantic quote search to your AI assistant via MCP. One command setup.

Purpose, meaning, identity, fulfillment, creativity, autonomy — all these things that positive psychology has shown us to be necessary for well-being are absent in the average job.” Most jobs today are a means for survival. Without their structure and support, people suffer psychologically and socially, as well as financially and even physically.