Go where the fun is

When you do something specific for long enough. People just assume you are an expert. They look at what you have done so far and give you more work. At the start you are probably doing it for free, maybe even paying to do it. All you need to do is give yourself enough time to build up that portfolio.

If you realize that, you realize you basically can carve out a career doing nearly anything. Ok, so what? What the heck should I be doing then?

Follow the fun.

I started this blog because I know it will eventually lead to something that lets me continue writing it. I have already been through this cycle before.

It was the reason I kept creating kept creating silly videos and eventually got paid to make a commercial. As far as my client was concerned, I was an expert. Look at the portfolio I built up! He had no idea I was jobless and $20,000 in debt at the time.

My skills were still meh, but it didn’t matter, I didn’t look like a student, I looked like a professional. I first met my client at a party.

I didn’t say “Hi, my name is James, I am learning to make videos. One day I will go professional.”

I said “Hi, my name is James, I make videos.”

My enthusiasm carried over as well. Part of why he took a chance on me instead of going a more established professional was how clear it was I enjoyed what I was doing. I talked passionately about my previous video.

Speaking of which, I got excited remember what it was. My previous video was about my Barber. I always find the craziest barbers.

I once had one in New Hampshire who turned out to be a refugee from North Iraq. He told me he a politician before becoming a barber and even showed me a picture of him with Saddam Hussein! He told me once he got to the USA, he had the ambition to become the #1 barber!

Saddam Hussein

The one I made a video about was very serious about hair. Every cut he would dress up in a 3 piece suit, put on smooth jazz, and dance around while cutting my hair. It was absolutely surreal. So obviously I asked him if I could make a video of him working as I found him interesting.



I never got a real job. I went straight to starting companies because it is more fun. I remember spending all my savings and then some in a crappy bedbug ridden apartment in Jersey City with my cofounders while all my friends from college were making 6 figures in the city. But I found my work fun. I would not have lasted in an office job.

Luckily enough, it only took a year and a half to break into Silicon Valley and get funding from Y Combinator, but I would have kept on following the fun for a long time even if we did not. I’ll have to tell that story in another post.

ALSO before anyone makes claims that it was easy, let’s be clear. I interviewed with Y Combinator 3 times before I got funded, it’s not like I got in the first time. I also had applied to every investor and incubator around the country that I could find and didn’t get any funding there either. Looking back now from years later, I know have an amazing job that I only got because it was clear I would have fun doing it. They trust me to be remote, they trust me to just succeed.

Look at it from the employer’s side. You want someone who is having fun with you. You don’t need to keep an eye on someone or do quarterly reviews if you know they love doing the work.


Everyone you meet wants to have fun.

Employers want you to bring that fun over to them.

This holds true for all of life though.

Your date wants to be with someone having fun.

The best teachers are having fun. Students engage better and find passions in subjects when they are exposed to someone having fun in that field.

If a co-founder, customer, or investor see you having fun, they want to join.

Here’s some similar sentiments from Elon Musk (Tesla/SpaceX Founder), Paul Graham (Y Combinator Founder), and the criminally underrated Danny Wallace (Yesman Writer/Comedian).



I have also recently invested in a few companies and I find myself going for the fun ones. At the seed and angel stage, most of it really is about the fun. I want to talk to these founders and be part of what they are making.


Besides all these benefits, this is the best way to be because you’re simply having fun. Pursue things you find fun. There’s a book on cleaning that was trendy a bit ago.

Spark Joy

The common theme was to only keep items in your house that give you a spark of joy. Similarly, only pursue things that give you a spark of joy.