Why I quit my job as an investment banker

There is an interesting phenomenon when it comes to working in investment banking. A lot of people desperately want to get into it, but a lot of people who are in it desperately want out. People want in because it pays very well, you learn a lot quickly, and it opens a lot of doors. They want out because, once they are in, those doors are opened and through them often awaits a better balance of high pay, more enjoyable work, and reasonable hours. I always considered myself very fortunate to get a job in investment banking, let alone doing technology mergers and acquisitions at Houlihan Lokey. I was still (and remain) very grateful for my 2+ years there between San Francisco (18 months) and New York (9 months), but a few months ago, at the end of September, I decided to quit.

I quit for a variety of reasons. When I told one colleague from another office that I was quitting without my next job lined up, his assumption was quick. He said, “You must really be pretty miserable then. Hey, I can’t blame you.” But that wasn’t the case. I didn’t love working well into the AMs some weekdays or being on call all the time and often having a lot of work to do on weekends, but I was not working 100 hour weeks spare maybe 2 or 3 over more than a hundred weeks in 2+ years. Sidenote: A lot of people in banking exaggerate their hours, but 70-90 real hours is still a ton and about as high as any person would want to go, trust me. 100 hours requires, for example, 10AM to 2AM Monday through Thursday (64 hours), 10AM to 10PM on Friday (12 hours), and another 24 hours however you want it (you don’t) on the weekend. Like I said, I only had 2 or 3 of those weeks and they sucked. The guy who assumed I was miserable probably knew I was not getting killed that badly but he figured I was fed up with dealing with a couple of particularly tough senior bankers. That was not it either. I have a pretty high tolerance for dealing with that sort of stuff so long as I have my reasons to do so. The truth was that there was no real reason why I was miserable because, like I said, I wasn’t. I felt very fortunate to have the option to continue doing what I was doing, but also, to have the option not to.

A lot of people take their first job after banking more because they want to get out of banking than because want to get in on whatever they are getting in on. They are often objectively great opportunities and no one usually questions why people take them except for the people themselves who cannot help but wonder if it is just another short-term step in some direction towards an ambiguous vision of a better life where “work” is enjoyable and life is better. I have never believed in “destination happiness”, the concept that if I can just get this or have that I will be happy. Don’t get me wrong, I believe in the value of making sacrifices and paying your dues, but not on an infinite timeline. After a couple years of abnormally hard work, I looked at my situation from a neutral point of view, crucially ignoring the illusion of the default which told me that I should stay at my job unless I had a clear and obvious reason to quit (like a next job lined up). I knew by this point that I did not want to rise through the ranks in typical investment banking fashion, so rather than stay until I found something else to do, I decided to quit and do anything else I wanted to do.

I appreciate the fact that I was very fortunate to have the freedom to make this choice. In 2+ years I had worked more hours than many of my peers would work in 3 or 4 years at their jobs, and as such I had earned income at a pretty disproportionate rate as well. I had saved enough money (outside of a relatively illiquid real estate investment) to comfortably buy myself at least several months of living without working in New York (or several years in Thailand, India or Vietnam, not that I wanted to do that). I had recently received my second year bonus and so with virtually no additional bonus money accrued (earned but unpaid), I could quit without feeling like I was leaving any earned money on the table (I would argue the bonus structure for junior bankers would be gone if not for its usefulness as a mechanism to trap solid bankers into rising through the ranks). Two of my three major deals had just closed and the third had just passed a critical checkpoint so I could effectively leave without screwing my deal teams. My lease was up at the end of the month so I was not tied to any large recurring payments (rent) and I would be free to travel wherever I wanted and I could even do so for a lower cost of living than my rent alone. A lot of people say that with a lot of things the timing will never be right and so you just have to do it. Fortunately for me, in the case of quitting my job, the timing was just right, so I quit.

I spent my first week without a job at home with my family in New Jersey. The next week Lauren and I had a week-long vacation in Praiano, Italy (an awesome little town between Amalfi and Positano on the Amalfi Coast). When we booked our flights a couple of weeks prior, I chose to buy a one-way ticket. I decided on my next destination our last night in Italy and spent the next week in Paris. That was followed by a few days in Copenhagen before flying to Tokyo for a few weeks traveling through Japan with my buddy Eric who was a couple of months into a year-long trip of traveling the world. I had some luck while I was traveling in that my investment in Tesla was literally paying for my travels as I went (part of why I sold too soon). Eric is currently a few continents in on his goal of running a marathon on all of them and so after training on his schedule for a bit I was in the best shape of my life running 30 mile weeks soon after Japan. I was home by Thanksgiving and started this blog on the 1st of December. I took the time to discover my interests and define my purpose. I started learning about big things like climate change and crypto. I applied for three amazing opportunities in VC, all of which I came across organically while following my interests, and one of which I have an interview for next week. I read some books, a couple of which I did not want to put down, and with my total freedom of time, I did not have to (recommend World After Capital by Albert Wenger and The Fixer by Bradley Tusk). As you already know if you have been reading the blog, I spent 10 days in Israel, celebrated New Years Eve in Tel Aviv, and now I am back home with a few more exciting things up my sleeve. This week (Sunday dinner through Friday lunch) I am going to try to eat vegan and gluten-free… we’ll see.

This blog is and will always be for me if no one else. It forces me to write every weekday and to have something interesting to write about and to do that I have to live a somewhat interesting life and learn about interesting things. I like that this blog serves as a public record and I sincerely hope that over time, more and more people read what I write and find it to be valuable or enjoyable to read, if not both, but at the very least, it is for me. This post is no different. My motivation to write it was to think about my response to the inevitable questions I will get about why I quit my job and how I have spent my time since. There are better and worse ways for me to craft an honest answer but the truth is so simple that it does not require any crafting at all. There were all of the reasons I mentioned and more for why it made sense for me to quit, and there were all of the things that I mentioned I have done since and more that have made me glad that I did, but when I throw my pros and cons paper in the garbage and let go of my need to justify my decision to quit, the answer is simple and clear. It all just feels right.