I’ve done it. I quit my job. Cue the “what have I done!?” tsunami.

Just joking. It wasn’t a rash decision. In fact, it’s something I’ve been thinking deeply about for a long time.

I’m 31 with nine years of experience in finance. Things have been going smoothly, or at least they appear to be from the outside looking in, but the recent reality has been an internal struggle as I face a growing dissatisfaction with my career.

The initial allure of working in finance wore off after the first few years, and the dissatisfaction started creeping its way in, ultimately morphing into full blown unhappiness over the last 2-3 years.

After a hell of a lot of introspection, I’ve come to be much more critical of my choices and my career, and I have more clarity than ever before about what’s important to me in life. This culminated in the decision to leave finance and go it alone.

To tell this story, let me run it back to ancient days of 2012…

I started my career in investment banking for a few reasons. I don’t know if they were the right ones, they probably weren’t:

1. I wanted to learn a lot (about anything, just a lot)
2. I wanted to “credentialize” my CV
3. Money
4. My friends were doing it, and I identified with the culture

Three out of four reasons revolve around one theme: preserving optionality. Knowing nothing about finance and having no idea what I wanted to do in life, that rationale seemed somewhat sensible, so I dove in.

Almost a decade later, it’s clear that I wasn’t being intellectually honest about who I am, where my true interests lie, and what I (maybe) should be doing with my life… stubbornly “preserving optionality” at all costs without thinking critically about these things. I can chalk it up to immaturity, lack of experience, or just not knowing until I know, but here we are.

Looking back on the last nine years moving through various sub-sectors of finance, two things occurred to me:

1. I was never organically excited about what I was doing. Every manifesto will tell you requirement #1 for being happy and successful in life is to love what you do. Ask anyone who knows me - I am an extremely enthusiastic person by nature. This never came through in my work. Big red flag🚩
2. My absolutely highest performing state occurred when I was out of a job and out there hustling to get hired by companies that felt out of my reach (in one case after already having left my job). My cognition and drive were on another level. I’ve worked on a handful of side hustles over the years and noticed the same thing. Something about the personal risk, upside, and lack of a salary safety net combined with pure organic interest unlocked something within me. This isn’t all that surprising, but sometimes it just hits home after the fact.

These realizations took me deeper down the introspection rabbit hole: How can I better spend my time to maximize my happiness and realize my full potential? What do I even like? What do I even want in life?!

Long story short, I distilled it down to this:

• Freedom. Not being a slave to my job. Living the lifestyle I want. Living in a state of pure meritocracy.
• The ability to travel, live a comfortable healthy life, and have a big family.
• To do something impactful. Having some sort of direct positive impact on other people or the world.

But what am I good at? More importantly, what am I good at that is relatively unique?

In an effort to prevent this post from becoming one big pat on the back, I’ll leave it here: I energize others, I can schlep like the best of them, and I’m decisive (I can “pull trig”, for better or worse).

Then, it dawned on me one day: I have been gravitating directly towards entrepreneurship.

Growing up, I watched my dad run his own business, and working for myself one day was always in the back of my mind. Unfortunately, I did not think that deeply about how to realize that future back then, and the underlying desire to build something of my own was eventually diluted by the distractions of college and the allure of finance.

I just assumed this would be my future. I never allowed myself to recognize that taking action was not only within my power, but a requirement. It only took a decade of experience and deep reflection to trigger that line of thinking.

So what now?

I started a company in Hong Kong, and we have a stable product getting positive early feedback from customers. But we haven’t found product market fit and are not cash flow positive (although we have a modest burn rate).

Some may say I’m derisked enough to take the leap, others may say I’m not even close. This is where risk tolerance becomes a matter of perspective. But regardless, even if this project wasn’t getting traction and I didn’t see a path to profitability, I’d quit my job anyway.

I recognize the importance of derisking decisions, but I also believe in the importance of leaning into your strengths and positioning yourself to get lucky.

I’m not advocating that people recklessly hang their hat on getting lucky without a plan. That’s akin to gambling. I’m highlighting the importance of putting yourself on the right side of luck relative to your current position, within the limits of calculated risk taking. Consider your current position versus the position you’ll put yourself in and what that will do to your chances of success.

I’m not superhuman and am pretty incapable of delivering the required level of focus when my peak mental hours are consumed by a day job. It’s also the leap itself that pushes me to my maximum productive output, so in my case, maintaining the status quo is anything but positioning myself to get lucky.

I think I’m well-positioned to succeed, and there are things I can do to further nudge the odds in my favor, including building passive income and maximizing my “at bats” through many small, controlled bets. But at the end of the day, I genuinely believe in myself enough to take the leap.

So, that’s where we are. After all that fancy introspection, it pretty much comes down to a good old entrepreneurial itch. And some itches must be scratched.

Sometimes you gotta burn the boats and bet on yourself. Away we go.

Thanks to Sarah for reading a draft of this post.