Five Life Lessons at 25

May 2022

A lot can change in five years.

On May 14th of 2017 (exactly five years ago), I would have been finishing up my sophomore year at Stanford. At that time, I wouldn’t have yet traveled abroad, had any real work experience, and I certainly wouldn’t have had the confidence to share anything publicly.

I was a different person at twenty. If I’m being self-critical: my worldview was limited, my aspirations misguided, and my character lacking in experience. But over the subsequent five years, which included a series of formative experiences and a great deal of self-reflection, I not only have a deeper understanding of myself but I also have a more effective playbook for living.

These are five valuable lessons I learned by age twenty-five that I wish I’d learned sooner:

1/ Learn to Compete with Yourself

The popular adage, “Comparison is the thief of joy” is true. A sure way to a miserable life is one of constant comparison.

Personally, I love competition. Having the opportunity to benchmark yourself against others, to learn from the more skilled, and to push your abilities in the process is an important part of the human experience. (Also, winning is just a lot of fun.)

But the “comparison trap” that comes with competition is an easy and dangerous one to fall into.

Many of the most important factors that will affect your life are outside your control. Your parents. The country you’re raised in. Your genes. None of us have a say in the hand we get dealt, only in the way we play it.

If you stop and think, comparing yourself to others makes little sense. Given your unique upbringing, genetic profile, and set of opportunities, what sense does it make to benchmark yourself against people with different starting points? It doesn’t.

The most effective approach to progress, I’ve learned, is to aggressively compete against yourself. (It also makes for a much happier life.)

2/ Everything’s an Experiment

Two insights helped me overcome social anxiety.

One was adopting a growth mindset - the idea that one’s conviction in their ability to improve can, itself, translate to greater improvement. I’ve found this to be surprisingly true in my own life. The second insight was to simply treat social encounters as experimental opportunities. 

Repeatable activities with low downside and tight feedback loops should always be treated like experiments: learning opportunities to see what works. 

Taking an experimental approach does two things: one, it drastically lowers the stakes of social encounters. If I do something wrong or say something stupid, I could just chalk it up to a failed experiment and try again. Second, and perhaps more important, is it encourages variability. 

What makes evolution-based systems effective is that the introduction of variability allows advantageous iterations to propagate. Without variability, the system can’t improve. This powerful principle can and should be applied to how we live. Deliberately introducing variability into one’s life (especially when the costs of doing so are low) provides more opportunity for improvement.

Most people confine their life by operating under a set of self-imposed rules. They allow themselves no room to experiment, and in turn limit their growth.

Life’s not a prison, it’s a playground. Learn to experiment more.

3/ Figure Out What Game Your Playing

After high school, I attended Stanford because that’s what you do if you get into Stanford. After Stanford, I joined Goldman because I was told it was the best place to start a professional career. At Goldman, I wanted to make Partner because that’s what I was told success looked like.

It took me too long to realize that with each stage of life, I was unknowingly opting into games I never consciously decided I wanted to play. This isn’t to say that any of these decisions were wrong, necessarily. It’s just to say that each of these decisions, goals, and desires were not a product of my own deliberate thinking.

When I suddenly decided to leave Goldman in May of last year, an MD on my team who I deeply respected said something that surprised me. After multiple failed attempts to keep me on the team, he said, “I wish I could have had the courage to do what you’re about to do [leave Goldman] many years ago. I wish you the best.”

Most people have no idea what game they’re playing. Others find out later in life but realize they’ve become captive by it.

Figure out what game you’re playing early. 

4/ Nobody Knows What They’re Doing

It’s just as true for the hourly McDonald’s employee as it is for the President of the United States. Nobody knows what they’re doing. Everybody’s just trying to figure things out on the fly as best they can. 

This isn’t to say that there aren’t varying degrees of thoughtfulness and intelligence that allow some individuals to make better decisions than others. Of course, this is true. But as a society, we grossly overestimate how much successful people have things figured out. The secret to success is that there are no secrets.

Some people are good at faking it. They can effectively create the impression that they know exactly what they’re doing. Fancy job titles. Polished suits. Complex jargon. Those in finance are skilled at this. But don’t be fooled. 

Over time, I’ve become less and less surprised to learn that people in successful positions (CEOs, government officials, university professors, etc.) know much less than I would have expected. 

5/ Develop an Action Bias

Newton’s First Law of Motion is: “Objects in motion stay in motion. Objects at rest stay at rest.” 

Referred to as the Law of Inertia, the Law applies just as much to how people live as it does to how physical objects move through space. Most people are “objects at rest”. Consumers. Passive observers. Static in nature. It’s unfortunate. 

The more experience and knowledge I acquire, the more I’m convinced that a large part of success is finding ways to build momentum. Until recently, my default has been passivity. To watch. To wait. To think before taking action. Now, while this proclivity can be of great value in high-stakes situations, in daily life this tendency for passivity often translates to no action being taken at all.

As the popular Gretzky quote goes, “You miss 100% of the shots you don’t take.” 

Learn to lower your threshold for action. Doing so will lead to more motion. More motion will lead to more momentum. 

In reflecting on these several life lessons at twenty-five, what most excites me is that there’s still so much life to be lived. Five years from today (when I’m thirty), I hope that I’ll think of my twenty five year old self in the same way I currently view my twenty year old self - as naive and inexperienced.  

Five years is both a long and short period of time. Until then, I’ll continue to rigorously apply these lessons I’ve learned and look forward to the many more I’ll add along the way.