Ambitious people often get stuck on popular paths pursuing prestige. It is an unfortunate but understandable phenomenon. Unfortunate because it traps people with enormous potential in relatively inconsequential industries like investment banking, management consulting, and law. But understandable because these paths make people predictably rich and perceived as “successful”.
It usually starts in high school. The highest achieving students compete to get into the most prestigious colleges — Harvard, Stanford, etc.. Then they compete to get into the most prestigious companies in the most prestigious industries — Goldman Sachs, McKinsey & Company, etc.. Then they compete for the fastest promotions, for the most prestigious exits, for more money and “better” jobs.
The problem is that these people, despite their consensus brilliance, often fail to think honestly about why they are doing what they are doing while they are doing it. They optimize their careers for what looks the best and what makes the most (money). Then they realize when they’re 40 or 50 that they succeeded by everyone else’s standards other than their own. Deep down, they know they could have done something more interesting, more fulfilling, more different, but they didn’t.
I was one of these people, and I could easily have ended up that way. I graduated from a Top 20 university and dutifully began my career in investment banking. I don’t regret either, either. But I am sure glad that I thought independently enough to start doing things a bit differently before I got stuck. Even before I graduated or got into banking, I started straddling the line between the prestigious path and a less predictable one. I dropped out of college after my freshman year and tried to start a successful business. The company failed, so I went back to school and then on to investment banking, but I got a taste of what it was like to do things differently than the other ambitious people around me.
So, after a couple of years in investment banking, I decided to quit. I didn’t know what I was going to do next, but I knew that quitting without knowing what was next was to do something different in and of itself, and I knew I wanted to do something different again. I ended up starting a blog, then a podcast, and then working full-time with Balaji Srinivasan, an extraordinarily unique individual himself, who I am proud to have served as Chief of Staff. Now, I know this is starting to sound impressive again, perhaps even prestigious, but it’s starting to sound a bit different too, and that makes all the difference.
I left my position with Balaji last year and took some time to think about things. I cleared my calendar, followed my interests, and trusted the process — I had done this before. That led me to working on a short-term project with Peter Diamandis after having him as a guest on my podcast, the same way I got started working with Balaji. Peter is another extraordinarily unique individual. Like Balaji, he believes in a future that is radically different from the present. I believe in that too. So maybe I’m a futurist, or a “tech guy”. From finance to tech — not so unusual. Even when I was in banking, I was in the Technology M&A group. That wasn’t just a coincidence — I sought it out. So this is starting to make more sense.
But just when you thought you had me pegged, I went and did something that had nothing to do with technology or the future. This winter, I was the head coach of a high school JV basketball team. I’ll also mention I made a rap album several years ago. I acted in a couple amateur short films. I wrote a book I haven’t published. I sometimes wonder whether I’ve done all these things for the same reasons those ambitious high school kids I mentioned earlier seek to stack as many extracurriculars as they can so they can look as impressive as possible on their college applications, but I am confident that is not the case.
Here’s the difference:
Many of those kids do those things primarily because they are impressive. I do these things primarily because I am interested, and if they happen to look impressive, that’s great. In fact, I believe many people would be likely to do things that look impressive if they stopped trying so hard to do things that look impressive. It’s the natural result of doing things that you’re truly interested in, of caring and trying to do your best at things you think you might be best at doing.
You see, the point is not to not look impressive. That would just be being contrarian for the sake of being contrarian. Rather, the point is to not follow the most popular and prestigious path just because it is popular and prestigious. The point is to think for yourself, to follow your interests, to do your best to find what you are best at doing and to do it to the best of your abilities. You want to be impressively different, impressively unique, impressively you.
All else equal, it is quite helpful to look impressive. It enables you to talk to people you otherwise might not be able to talk to. It opens up opportunities that otherwise might not be available to you. But it is NOT important enough that you should sacrifice following your interests for the sake of looking impressive.
Impressiveness is incredibly useful as a secondary benefit, but utterly detrimental as a primary pursuit. The challenge is trusting that you will get where you want to go, or rather, that you will be grateful for the going when it is all said and done, even though you can’t know where you’ll go.
The popular paths pursuing prestige are predictable. There’s a comfort in that. You can be 22 with great confidence that when you’re 42 you will have plenty of money to support your family. You’ll be viewed as successful and no one will question anything you ever did. You’ll have done everything right.
It just might feel wrong.
