In my first 27 years of life, I told myself I was an entrepreneur at least 10,000 times. I was convinced. I still am. Looking back, it’s odd that in that time I started precisely 0 businesses and made exactly 0 dollars from my own ventures.

We often hear from guys like Noah Kagan or Zuck about how they sold businesses to Microsoft at 14. They couldn’t help themselves! I thought of myself in a similar vein, but I put 100% of my effort into school, activities, and building my resume. I had only one goal in mind – Stanford. I felt everything would work itself out from there. 

At 10 years old, if you asked me what I wanted to be when I grew up, I would have said “rich”. It’s part of my DNA, trust me. But I didn’t plan ahead. I just told myself, Stanford, Stanford, Stanford. If I had thought ahead, I might have realized, the real goal was to get into Stanford to meet the right entrepreneurial people, find a path to massive wealth, and sprint down that path. Even at 10 I think it would have made sense to me.

But I didn’t do that, I looked at the traditional ladder of success and was ok climbing that as fast as possible. I never thought I could be successful without Stanford. I never thought I could start a company as a kid! But I could have. Kids definitely can today. The founder of Ethereum is 24!

I also noticed that once you’re on the ladder, you don’t focus on yourself as much. You look to your left, and your right, and you see other people climbing ladders toward your end game. Oh shit you realize…you’re in a race! This was a tremendous source of motivation for me from 0-21 years of age. I loved competition, and I thrived on it. I bested my peers and felt good doing it. But then in a vacuum, I didn’t like what I was doing.

At Goldman, when I was still on the ladder, I might occasionally see someone in a completely different arena, say surfing or something (lol). And I would think…dang they look happy. I wonder how they got to do that. But then I’d see someone close to me catching up to me on the ladder, and I’d get anxious, and I’d keep climbing!! I find the high-achievers mind is susceptible to competitive forces and thus shuts itself off from opportunities, consciously and subconsciously.

We almost don’t WANT to see different paths or amazing opportunities because we risk our place on the ladder. How sad! But it’s our nature. One of the best things I did before freelancing was take a sabbatical. One month, no work. No intent but to work on my body and make it feel good again. My mind…starting accepting requests again. Team Health – open for business!

I started seeing things I was missing all along. I could do email marketing for a Shopify client. I could read a crypto whitepaper. I wasn’t climbing a ladder next to anyone anymore. I was just chilling on my own island, doing things I found interesting. Some people have always been this way. But many high achievers like me are not.

Freelancing is about building your island, and it’s beautiful. Sometimes, I miss the competition. But I think in time, I’ll find it again – this time it’s just me vs. me. It’s also hard to convince yourself you enjoy something when no one else’s opinion matters. When I do things for me, I’m just happier.

At that, I have settled on a crypto/behavior design idea that I’m going to build. And it’s not to solve some massive market dislocation, it’s just for me. To help me achieve my fitness goals. I don’t care if everyone likes it or hates it, I’ll use it. So I’m building it.

Man, it feels good to be off the ladder. I hope you can do it soon too.


Freelancing Series - 7 - The Ladder