Why I didn’t go to law school

I wrote up the explanation below a few months ago when someone sent me an email thanking me for my LSAT guide and asking me why I didn’t go to law school.  I ended up sending the guy a one-sentence explanation instead, but I figured the full explanation would make a good blog post, and I’m just now getting around to posting it:

It was for a bunch of reasons.

Before I got my LSAT score I was dead-set on going to Harvard. It was Harvard or bust. But once I got my score I realized that I not only had a shot at Harvard, but also a shot at the even-more-prestigious Yale, and I started to wonder if I should try to make a serious attempt to go to Yale instead. I knew my LSAT score was valid for 5 years, and so getting a perfect score got me to start thinking about waiting a few years before applying so that I could improve my resume and increase my chances of getting into Yale. I decided to move to Washington, DC for that reason (improve my resume).

Also, now that I was sure I could go to Harvard, it lost a lot of the mystique that it’d had for me, and I started to wonder if I really should go to Harvard (it’s like that Groucho Marx quote: “I don’t care to belong to any club that will have me as a member.”). ~2-3 months after getting my LSAT score I went to visit Harvard Law School, sat in on some classes, and talked to some students, and I left a little unimpressed; I got the impression that most of the students were smart people who didn’t have a strong sense of what they should do with their lives, and so they had just followed the beaten path to become a lawyer; that also described me. I got a bad feeling from this, because it seemed like a bad way to make such an important decision (the decision of what skills to learn), especially given the news that was widespread at the time that the country was producing too many lawyers. For many, many years (at least far back as high school, if not earlier) I’d been mystified at how people end up in different careers: how did people decide that they should dedicate their life to X instead of Y? I’d always been more of a dabbler and dilettante, and I couldn’t understand how people could do the same thing for years without getting bored. So in high school, I had no idea what career I should go into, and that continued into college. Now I was at a point where I had to make a decision (about what career to go into), and so I made the decision that I wanted to spend the time necessary to arrive at a crystal-clear idea of how to make the decision of what career to go into, even if that meant spending years thinking about it. This train of thought (“I need to figure out how to make this decision”) was something that had probably started soon after I graduated from college and started reading autobiographies.

So to summarize the above, the decision to wait a few years to apply to law school was a result of a combination of 1) me deciding that it couldn’t hurt to try to improve my resume, and 2) me deciding that I should really do research and develop a crystal-clear understanding of how to choose a career.

Once I was in DC I interned for a Congressman, worked a cubicle job at Thomson Reuters, and temped at a few different law firms, and I eventually realized I would be miserable if I had to wear a suit every day, stay in an office (I hate offices), be around people I don’t really care about, etc. I realized that the marginal benefit of the money I could get from being a lawyer wasn’t worth the marginal cost in terms of my freedom.

From doing a bunch of reading, I realized (like many people who go into law seem to realize, such as Peter Thiel) that if you are willing to pay the price (in terms of lifestyle) that you need to pay to become a lawyer, you can have a lot more upside if you go into finance instead of law (e.g. become an investment banker / go work at Goldman Sachs). Peter Thiel did this exact thing: he started in biglaw, then switched into finance because he could make more money there. And then in the summer of 2011 I learned about Michael Burry, who runs a hedge fund from his house, and I thought, “Wow, I’d love to be able to make a lot of money while living and working from anywhere”. So for a while I was thinking I would try to become a hedge fund manager a la Michael Burry.

After learning more about Peter Thiel and how he then switched from finance into tech, I realized that tech (internet entrepreneurship) had some characteristics that I really liked: 1) it was a younger industry, and so it seemed like there might be more opportunities than in the further-developed hedge-fund industry, 2) it seemed much easier to be able to get a job where you’re working remotely, and so even if I never made a ton of money, I knew I would be much happier if I could work remotely, so my downside was better protected, 3) it seemed possible to make a huge amount of money if I hit upon the right idea, so there was the same potential for upside that I would have gotten if I’d become a hedge fund manager. Nowadays I think of entrepreneurship as just being an extension of finance; an entrepreneur is like being an extremely-hands-on activist investor.

I also quickly realized that I didn’t want to suffer in the short term for some longer-term benefit, so I wanted to try to maximize my happiness ASAP. So in early 2012 I set a five-year goal for myself and a 10-year goal for myself: the 5-year goal was to have a job / career where I could work remotely from anywhere in the world, and the 10-year goal was to start my own tech company or hedge fund. I’ve achieved my 5-year goal and I’m now working on my 10-year goal. There’s one guy in particular that I’m interested in emulating for the next few years, his name is Pieter Levels (check out makebook.io).

My impression is that many people who contact me about the LSAT are very entrenched in their social group (their family, their friends, etc.) and they don’t feel comfortable doing something radically different from what their peers / family are doing. For example, they want to get their career going in X number of years so that they can get married and have kids within Y number of years. I didn’t want to live that way, but many people do want to live that way. I think it’s probably the #1 factor that determines whether the non-traditional path I chose is a good fit for a person or not.

Also, as a post-script: I have a friend who went to Stanford for computer science and had started several (failed) internet companies, and after he graduated he wanted to go to Harvard Law School and become an IP lawyer instead. I told him not to do it, that he should just keep trying to start new companies instead. He ignored my advice, got rejected from Harvard Law, accepted to Georgetown Law, worked his ass off his 1L year to be at the top of his class, successfully transferred to Harvard…and then realized he hated it and ended up skipping classes so that he could start new internet companies instead. Now, I do suspect the credential is providing him some benefit, but he apparently has well-to-do parents who could help him with the debt payments if everything went south. In my case I would’ve had to pay off the HLS school debt myself, and I just didn’t think the benefit (in terms of prestige) that it would provide would be worth the cost if I knew that I wanted to start an internet company and not become a lawyer.

You can find more of my thoughts on this topic here: My Thoughts on Various Topics – Whether to Go to Law School

If you found this interesting, you can follow me on Twitter.