September 30th, 2020
Two days ago, I went to a fancy restaurant in a t-shirt and running shoes.

I didn’t do this in a cool, counter-culture way either, I did this because I don’t travel with a nice button-down or fancy shoes, and it was too last minute to borrow/buy one.

I felt embarrassed. It made me ask the question that I ask myself almost every day: 

“Am I too old for this?”

“Am I too old to be working on apps? Am I too old to be traveling? Should I settle down in one city? Should I own a car, a watch, fancy clothes, a Peloton, an Equinox membership? Should I get a dog? Should I just go get a ‘real’ job?”

If you’re also an entrepreneur, you'd probably tell me I'm talking crazy.

But to most “normal” people, I probably look like a "lost teen"

What’s a “lost teen"? It’s someone who hasn’t figured out what they want to do in life, wandering around, not making progress, and wasting time.

This is a constant struggle for me. It’s so hard to explain to people what I do. Some of my closest friends still have no idea that I’m even making money. They still think I quit my job to work on a stupid blog…

A Story

A few months ago, when I was back home, I ran into the “popular girl” from my high school.

Her: “Omg Pat I haven’t seen you in 10 years. What are you up to!?!?”

I was with my sister, and she jokingly told her that I still live at home and I’m not employed, which at the time, was technically true.

While I laughed, my high school instincts kicked into high gear. I wanted to blurt out that I actually run my own successful company. I wanted the popular girl to respect me.

But I didn’t blurt it out. I didn’t need to prove that to her. I just kindly asked her what she’s up to, and she went on for about 20 minutes about how she’s getting her real estate license.

In that moment, I was afraid that she would view me as a lost teen. I was afraid she’d think that I didn’t make any progress since high school. Since I was never cool in high school, I wanted the cool girl to not think of me as a loser.

But the reality is, she doesn’t care. 10 minutes after our interaction, she probably forgot all about me. I likely never crossed her mind again. My fears of being viewed as a lost teen are only in my own head.

Embrace Your Lost Teen

I have to remember that being a lost teen is what leads to success, in all cases.

If I didn’t act like a lost teen, I wouldn’t have started a rap group in high school. I wouldn’t have moved across the country to California at 17. I wouldn’t have done the coding boot camp. I wouldn’t have traveled the world. I wouldn’t have started a company.

In my 20s, it was socially acceptable to act like a lost teen. But in my 30s, it’s getting a lot harder. I need to push back on this narrative even more now.

Anthony Bourdain didn’t succeed until he was 46. Bourdain is the epitome of a lost teen: He traveled the world for a living, yet, he’s also one of the most respected people of our generation.

My dad is also a lost teen. He lives in Wyoming and does yoga every day. He only owns one pair for $30 jeans. He started multiple businesses in his 50s and 60s.

I have to push back on the narrative of having things all figured out by 35. If I’m still a lost teen at 64, I’ll have won the game of life.

So let’s wear our $10 t-shirts with pride, because that’s exactly what these lost teen billionaires are doing: