End of an Era & Lessons for the Next Chapter

Is it just me or does 2024 feel like it's flying by? Hard to believe we're already nearing the end of July and pretty soon we'll be into the fall months and making plans for the holidays.

2024 has already been quite an eventful year for me and my family. In July alone, I turned 35 to officially join the late-30s club, left my job of 11 years in private equity, and pivoted into a brand new career at Google. All the while, Tiffany and I continue to wing this parenting thing with two babies at home.

When I’m old(er), looking back on the story of my life, I’ll have this chapter marked as one of transition and new beginnings.  

End of an Era

I joined my last company in 2013 as a spry 24-year-old. I was a kid just trying to figure out my place in the world, which at that time meant making enough money to fund my hobbies of partying and working out. A lot has changed in those 11 years - a wife, two kids, two dogs, five apartments. It's a lifetime.

I remember how excited I was to start. Fresh out of a two-year stint in investment banking, I about to enter the high-flying world of private equity at one of the most successful infrastructure investors out there. It would be a huge step-up in prestige (that stuff matters in the industry) and the work was supposed to be more interesting with better pay and hours. It was all supposed to be better.

I drank all that kool-aid.

As with everything in life, reality always turns out a little different than expectations. I worked just as much, if not more. The work was more interesting but far more challenging. I certainly didn’t feel like I made more after NY income taxes and rent. At the end of the day, it was still a junior role in finance and my days largely consisted of the same calls, meetings, and staring at Microsoft Office until my eyes bled for 70+ hours / week.

But overall, it wasn't too bad. I liked most of the team, I learned a lot, and the money was, to quote Larry David: "Prettay, prettay good". Sure, it wasn't perfect but I could do a hell of a  lot worse. I think the ability to endure when things aren't great or sometimes downright painful is seen as a virtue in Chinese culture. I did just that. I endured. I got promoted a few times along the way and then one day I looked back and I had spent over a decade of my life there.

If I'm being honest, I probably should of left a few years ago but I stuck around due to some combination of inertia, fear, and comfort. I always knew that I didn’t want to be one of the senior guys at the company. They lived and breathed the job. I never had that passion. I was all too happy when a deal died and I got my weekend back. But it’s easy to push those concerns to the side when they seem so far away and the next bonus check or promotion is right around the corner. You keep kicking that can down the road until all of a sudden you doing exactly what you never wanted.

I ended up sleepwalking through the last few years, never fully engaged with my work. Being in that place in a job or any relationship sucks. You’re not excited to show up. You’re not growing. You’re just kind of there… going sideways. Some things just run their course. It was time to move on.

I genuinely believe that everything happens for a reason, even a few years that feel wasted overstaying at a place I was meant to leave. It’s all led me to where I am today and there's no place else I'd rather be. I’m excited what's next and grateful for everything that happened on the path to get here – the good and the not-so-good.

Lessons for the Next Chapter

Here are a couple of lessons from the first chapter of my career: 

1. Take risks, don’t fear failure: 

I never really took a risk with my career. I’ve held two jobs with the most recent for over a decade. It’s safe to say I was a bit risk averse. But in hindsight, I feels like I let the phase of my life where I should’ve been taking the most risks pass without ever taking one. Your risk tolerance will only go one direction as you get older. Down. But there will always be room for calculated risks.

Mark Zuckerberg has a great quote: “The biggest risk is not taking risks.”

I think we tend to overestimate the downside to trying something new. It’s one of the reasons I stuck around for so long. I feared the alternative. What if I fail? What if I don’t fit in? What if [insert excuse or fear]?

Well, what if you don’t?

The worst thing that can happen if you fail, is you go back to doing exactly what you’re doing now. But at least you tried and you'll walk away with new perspective and learnings. When measured over the rest of your life, those experiences will be be worth it.

2. Don’t be rational, be reasonable 

In The Psychology of Money, Morgan Housel gives an example in investing to illustrate the difference between rational vs. reasonable. Being rational relies on pure logic and analysis for decision-making. Being reasonable considers other elements like emotions, practicality, and social dynamics to come to a sensible solution. In essence, it’s the difference between IQ (rational) and EQ (reasonable).

Most of us are building wealth over a long-time horizon (20-30+ years) to eventually retire. The rational strategy, the one that works in a spreadsheet, is to take on as much debt as possible and put everything you have into equities. You might lose it all in a market downturn, but the math says you’ll still end up in a better place even if you have to start over from zero a few times. Just roll it back and lever up.

Most people sane people do not employ that strategy. They want to avoid bottoming out. Who wants to explain to their kids they have to move because daddy lost it all speculating on Gamestop? Even more crazy would be someone losing all of their life savings trading on margin and then employing the exact same strategy again because that’s what the math says works. Instead, most people just diversify and put their money in some vanilla index funds. It’s reasonable.

Every single time I considered leaving my job, I always made the rational decision to stay. Every one of those decisions made sense in a vacuum. But a series of rational decisions can lead you to a place you never wanted to be. Sometimes you have to throw logic aside and listen to those other voices. It might not be rational, but it’s reasonable.

3. Make a life, not just a living

If you ask people why they got into investment banking / private equity, money would be one of the top answers. For a recent college grad that didn’t grow up around much money, investment banking provided stability and a lifestyle that I could only dream of growing up in a Chinese immigrant household.

But making a good living is not the same thing as having a great life.

Are you able to see your family? Are you in control of your time and schedule? Are you working with people you like? Are you engaged and interested in your work? Are you doing things that make you feel alive and full?

These are the elements that make up a great life. Real wealth comes from having the freedom and time to do what you want to do. Prioritize living a great life and then make enough money to support that.

4. Slow down and enjoy the moment

The investment banking / private equity career track is an adult hamster wheel. You are always focused on the next thing - the next deal, the next bonus, the next promotion, etc. You fall into the trap of believing that once you achieve that next thing, you can finally relax and enjoy life. But those moments achievement come and go, only for you to fall back to same grind immediately after.

I don’t think this is necessarily unique to finance. We all lead incredibly busy lives. It’s easy to get lost in it. You hurry through everything on you need to do because there’s always something else to do. You end up missing out on life around you and the things that really deserve your attention – your family, your friends, yourself. 

The good old days are happening now so slow down, take a breath, and enjoy it.