Why Quitting My Job is a Safe Investment

I wrote this in March/April 2024 as a note to myself as I was thinking through actually leaving my investment banking job of about 10 years at the time. I hadn't shared this with anyone.

I finally executed the plan and left my job in February 2026. Better eventually than never.

I decided to quit my job, the only career I’ve had. I’ve been in the same job at the same company for all but 7 months of my career. I learned a lot and enjoyed it at times, but I’ve come to the realization that it’s not enjoyable or satisfying enough because there’s much more I want out of my craft and out of my life.

You might be surprised or wondering why I would take such a “risk,” when the job has been going well over the years, pays very well and has put me on a very fortunate path which has brought me other really good non-work things in life. Especially now, when I am just a couple of years away from making it to the top of the investment banking title hierarchy, Managing Director. With that title and role, the earnings potential can multiply well into the seven figures.

Why now walk away from a really good career, one I wanted from the start and that I would have been ecstatic to have this long coming out of college?

The thing that convinced me – and it took a while – the bigger risk is to stay in this career. Quitting now might turn out to be one of the best career decisions I will ever make.

How did I get here?

About a year ago, work started to slow down compared to how busy I’d been a couple years earlier. My employer was acquired by large bank, which brought a lot of change to my team specifically – a business area we covered was effectively shut down by the larger bank (from a risk management perspective) and a senior member of my team – who I worked with for about 7 years, learned a ton from, and became a close mentor – decided to leave the firm. The overall market for investment banking business was also slow because of broader market factors like inflation, and as a result, rising interest rates.

With more time on my hands, I found myself reading a lot more books than I had been during my working years before this. I read books when I was growing up, but once college came and I started working, I didn’t read much more than a book or two per year. It didn’t take me long to realize I missed it. I think the reading also helped reignite a passion.

The reading became dominated by books about business or self-performance or self-improvement. I remember one of the earlier books which started my new wave of reading was Ten Year Plan, which is a book about the founding of the restaurant company Tender Greens – the same company I spent the other 7 months of my career working outside of investment banking. It was written by a couple of the founders, who I came to know a little bit during those 7 months. I think I read that thing in less than two days. The story of a business, particularly one which I knew a bit about, was something that was easy to devour.

I was also spending more time listening to the only podcast I’d really ever listened to consistently in the past, The Tim Ferriss Show, where the host Tim Ferriss focuses on “deconstructing world-class performers.” Paying more attention to his work and his guests also led me to more books, which in turn led me more podcasts, which in turn led me to more books, and so on. As this process went on, I was getting closer and spending more time with the subjects that really interest me. One of first one of those books was Ed Thorp's autobiography, A Man for All Markets.

Spending more time with these interests quickly grew the list of books and podcasts I wanted to get through. There was definitely an excitement to the discovery but there was also a realization that the time required to read and listen to all of this interesting stuff was also growing.

Certain things I was reading, like the Almanack of Naval Ravikant, some of Paul Graham’s essays, including How to Do Great Work in July 2023, Warren Buffett’s annual letters to Berkshire Hathaway shareholders and Warren Buffett’s Partnership letters, also gave me a lot of nudges and opportunities to think more about how I’m currently spending my time and whether my current “career” is actually what I want to be doing.

It ultimately felt like it’s very unlikely that investment banking is the right career for me to keep going in because I am simply not drawn to that craft and I don’t get up in the morning thrilled to do that job. It doesn’t give me energy.

There are a lot of things I don’t like about the investment banking job, but some important ones: I don’t want to navigate a large organization and go through a bunch of processes to get work done or comply with organizational procedures; I don’t want to be restricted to a single industry or sector; I don’t want to be transaction oriented or single-mindedly motivated on getting the next fee, all of which is more aligned with short-term thinking. I also don’t want to be directed micromanagerially by certain leaders or managers or clients how to spend my time.

My ideal environment will allow me to focus and spend time according to what I value or gives me energy: curiosity, learning, independent thinking, long-term thinking[1], self-reliance and lack of constraints which leads to the freedom to make decisions and experience the results. 

How do I feel so strongly about quitting?

The short answer: I don’t wake up in the morning excited to go to “work” or do my “job.” And I believe that feeling definitively possible to find.

It sounds idealistic, improbable and potentially selfish. It even feels selfish to say that I think it’s possible, and believe in that so much that I’m actually quitting the job. It even feels naïve at times. Where are all of the rational people who are quitting their “successful” careers early in the decade they get married, buy a house and start a family? What about all of the money that’s sitting there for the taking just one year from now, and the next year, and the year after that? The benefits and health insurance? The stability and predictability of a salary? And for me particularly, the tenure of almost 10 years at a company and in a team where I know how to operate nearly on autopilot?

I question myself internally very often over the decision to quit, including the questions I just asked. I don’t have an answer other than this is what feels right to do. I will say the decision wasn’t made suddenly. It was an idea that grew naturally over a period of time when I was doing more reflecting than I’ve ever done in my adult life and spending more time exploring my curiosity and interests more than I’ve ever done since I started working. I feel like I was pulled to make this decision.

Finding work we love doing so it doesn’t feel like work is obviously something everyone would like to have. If it cost us nothing and there is no risk to getting there, everyone would want that. Obviously, that is not the simple world we live in.

It’s respectable, reasonable and makes sense that people don’t end up trying to find the career or work they love doing. A couple sensible reasons: minimizing the financial risk of raising and supporting a family (especially once comfortable financials are already achieved or secured) and having other values in life that are more important than feeling excited or fulfilled in a job.

Another reason I think we are not great at finding work we love is that it’s simply human. We are programmed to preserve the status quo – it’s a survival and social inclusion instinct. Preserved long enough, the status quo of career, whatever it is, becomes our identity or part of our identity. And when we’ve established an identity, it’s very hard to change it. Even if we have thoughts of changing it, it’s much easier to go “just one more year” in that identity, and at that point, we agree with ourselves to reevaluate.

The problem, I think, is that those years go by like this, one-by-one, and they add up quickly. For a lot of people, a lot of the time, I would guess they add up to a whole career, and this realization probably comes with a weight of regret later in life. A whole career is usually a huge percentage of our waking hours and therefore our life. For me, I’m coming up on 10 years in the same job at the same company, and for most of that time, it has felt like an identity that would feel painful to unravel or change. A single thought and reminder of that potential pain is often alone enough to suppress that fear for a while longer. And I’ve learned I’m very good at suppressing things – self-discipline and wanting to avoid confrontation helps with that – but being good at suppressing strong feelings – toward myself or others – is not a good thing.

What’s important?

“Time is the stuff life is made of.” I didn’t actually know who was credited for saying this until I looked it up when writing it here. It was Ben Franklin[2]:

Dost thou love life? Then do not squander Time; for that’s the Stuff Life is made of.

Time is the bottom line – none of the best things in life, like loving families, high-quality and long-term friendships, self-improvement, leaving your impact on people/places/things, traveling, eating great food, watching the Packers – can exist without time. Obvious, I know.

While time is the stuff life is made of, the quality of that time might even be more important. Or maybe they are hand-in-hand or in other words the same thing. I think this multiplies the importance of how we choose to spend it. So, for me, I think it’s time to take some swings at optimizing the quality of my time, which basically means it’s time to take some swings at optimizing the quality of my life.

A definition of risk I really like is the chance of permanent loss (credit Warren Buffett). So, when we’re talking about life, where time is the bottom line, the permanent loss of time is one of the biggest possible risks we can take in life. Permanent loss of time can come from death, or more likely, and more in our control, it comes from not liking or enjoying how we spend our time.

Permanent loss of time would mean looking back many years later having avoided or having chosen not to spend my time doing things I had felt pulled or compelled to try or do. These are most likely to be things that I was really interested or curious about, things I might really enjoy or things I might really enjoy AND potentially excel in doing.

Jeff Bezos has talked about thinking through this idea when felt compelled to quit his high-paying hedge fund job to start a company that sells books online. He calls it the Regret Minimization Framework[3]. When faced with a big decision, he projected himself forward to age 80, looked back on his life, and thought whether the decision would contribute to minimizing the number of regrets that he had. He said, “I knew at age 80, that I was not going to regret having tried this…I knew that if I failed, I would not regret that. But I knew the one thing I might regret, is not ever having tried. And I knew that that would haunt me, every day. And, so, when I thought about it that way, it was an incredibly easy decision.”

He also left his job in the middle of the year, probably walking from a hefty bonus that was effectively half earned but not paid (it’s not yours until it’s paid). He talks about how, if we use the Regret Minimization Framework, it removes the confusion of short-term things like the next bonus and gets us thinking more about the long-term. Without his story of creating Amazon, we obviously would not have heard the story of a guy quitting a stable, high-paying job to start an eventual trillion-dollar company (survivorship bias) – and we certainly don’t hear the stories about the people who try and fail and go back to doing what they were doing. I would be willing to bet that even those people did not regret they tried because it led them to a more fulfilling path less likely to result in a permanent loss of time.

When thinking through future potential regret, it’s pretty clear to me that NOT trying a “career” change is the big risk – the chance of permanent loss of time, permanent loss of life.

More thoughts on regret

It’s not just the potential regret of a massive permanent loss of time. It’s the regret that could come from knowing I suppressed all of the moments of inspiration I’ve had to go after what I really want to be doing, instead of what I should keep doing because it’s what I think other people think I should reasonably be doing.

I’m guessing we all have moments like this that come to us randomly, where we feel inspired by thoughts that seemingly come out of nowhere about something we know we want to be doing or achieving with our life. Maybe these are subconscious reminders of what we really want to be pursuing if there were no external or societal constraints holding us back.

These thoughts also make me feel a little crazy – who am I to believe I could actually be the guy who could do something like that? Or I look at people I admire, for example highly successful investors, and I think the chance is very low I will rise to that caliber of achievement. But then the idea keeps coming up and keeps me thinking about it. It’s hard to deny this as an intuition.

So that’s the other form of regret I want to avoid. And to do that, I have to not only listen to these intuitions but act on them. I don’t want to be sitting here decades from now having forever suppressed them.

How do I know where to go from here?

I’ll never know with 100% certainty until I actually do it, but I am 100% comfortable with that.[4] I have a pretty good idea of I want to spend my time doing and that’s going to have to be good enough.

There’s something I’m willing to bet on: Curiosity.

Back to the Paul Graham essay, How to Do Great Work from July 2023, which talks about curiosity being the best guide:

“There's a kind of excited curiosity that's both the engine and the rudder of great work. It will not only drive you, but if you let it have its way, will also show you what to work on…

What are you excessively curious about — curious to a degree that would bore most other people? That's what you're looking for…

Curiosity is the best guide. Your curiosity never lies, and it knows more than you do about what's worth paying attention to.

Notice how often that word has come up. If you asked an oracle the secret to doing great work and the oracle replied with a single word, my bet would be on ‘curiosity.’

What do I want to spend my time doing? It’s where I have a lot of curiosity – where my reading and other listening took me – learning about how the best businesses work, particularly in the context of investing. If I go back to what I really found intriguing when I was young, it was business and how businesses made money. My favorite games were tycoon games on the computer, Monopoly and Payday. I liked figuring out how money was made and the continuous, incremental improvements over time for doing so.

I have a lot to learn, but I think that to find out how businesses do well, you have to figure out how the world really works. It’s a hunt for the truth that involves endless learning because the world and economy doesn’t stop changing. This is exactly the kind of game that I don’t think can ever get old.

Endless learning and continuous improvement are concepts I’ve always been drawn to. It’s also the abstract thing I’ve had the most non-verbal thoughts or visualization about, if that makes any sense. By that I mean it’s not something that I always think about in terms of words – I’m drawn to the feeling of incremental progress over time and the feeling of slowly building something in small pieces that eventually amounts to big progress or improvement or results. There is fun in being in that process knowing it is building and improving and the result will come.

Playing games in business I think will satisfy that with ease. No matter how much the world changes over our lifetime – maybe the only certainty – in a capitalistic economy like the United States, we will always have businesses to provide something of value by doing what that business does best.

Investing in businesses is the craft I’m drawn to. The interest in business, the values I mentioned earlier, and the traits I think I have, are all what make me feel compelled to give it a shot. At least, I have to try, I’d regret it if I didn’t.

What are the relevant traits I think I have?

If you know me well, I’m sure you can attest, I’ve always been interested in a debate if I had a strong view about something. It gets me fired up to learn about something then share my view, which can come across more forcefully than it should. This is a blind spot of mine – I have held “wrong views of the truth” and I’m sure I will be wrong again, many times – but at the end of the day I just want to know the truth, recognize it and use the learning to get better for the next time.

I’m very competitive. I want to win. I’ve long been a sore loser – from board games to video games – though I like to think my emotion management skills have improved in my adult life. Put me to the test – give me an Xbox controller and I promise to keep it functional this time.

These two traits together make another. I enjoy doing something in a different way based on my own decisions and coming out ahead as a result. In other words, it feels rewarding to be proven right when holding a different view.

This makes for another blind spot or vulnerability, which is gaining satisfaction from the recognition or acknowledgement of others of the work or result I have delivered. And another, which is being contrarian for contrarian’s sake.

But all of that said, what I really like to be doing is improving by getting a little better, getting a little smarter, and exercising the discipline to do so. I really like figuring out how the world really works and then incorporating that knowledge or improvement for the next time.

Investing is a game that I think delivers all of that, in the subject I’m most interested – business.

What if I “fail?”

I’m not sure what failure would look like. I feel compelled, and confident, that I want to try investing because it would cross of a potentially huge life regret. If I try, and I’m bad at it, how is that a failure? Maybe it’s a success, because I will have gotten the clarity that I wanted.

I also need to learn this by doing it and thinking back on it later, but I suspect very strongly that too many people overestimate the gravity of downside risks in things like a quitting a job or moving or whatever life decision that seems daunting at any given time.[5] The reality is that it’s pretty likely you can go back to doing whatever you were doing before you made and carried out the decision. Like in my case, it’s pretty likely I could get another investment banking job in a few years. Most decisions probably aren’t irreversible. They’re just perceived as potentially painful or hard – that’s the status quo bias, that’s being human.

Thinking about my life, I haven’t really taken a lot of “risks.” I went to college less than 30 minutes from where I lived my whole life. The biggest one probably came after college, moving from Wisconsin to California to take my job in the first place. I moved across the country to a city or area where I had no family or friends, for the sole purpose of focusing on my career. If things didn’t actually work out, I’m sure I would have moved back to Wisconsin or moved somewhere else or tried a different job. That would have simply been just one path of the many I could have been on. So being on a path and then avoiding going on a new one – which is just one path of so many possible ones – doesn’t really seem like it should be a big risk.

[1] I think long-term thinking, delayed gratification and lengthening your attention span are going to be increasingly valuable competitive advantages in most disciplines. Social media and online connectedness has trained us to prefer short bits of information, bursts of attention and immediate social approval.

[2] Charlie Munger idolized Ben Franklin, one of the members of what he called the “eminent dead,” accomplished dead people who he encouraged we read about and learn from. As of November 2023, Munger is one of them.

[3] https://youtu.be/jwG_qR6XmDQ?si=yDq9cv-ys1kQDPH9

[4] Another Bezos concept is that you should be making decisions with 70% of the information that’s possible to get. If you don’t, you’re not going to be quick enough to realize opportunity.

[5] Tim Ferriss has an exercise/tool called Fear Setting. Haven’t actually used it fully but it basically gets you to realize that if you think of what you’re afraid of, there are a lot of things you can do to mitigate or realize that you’re overestimating the fear.