Fifteen Years as a Creator. (I’ll Never Make It.)

Five years ago, I wrote about how — after ten years as a self-employed independent creator — I hoped to “make it.” I now realize, I never will.

Brainstorming a project, circa April 2009. (Photo by Ryan Halvorsen)

Five years ago, I sat at my keyboard to have a serious conversation with myself. It had been ten years since I had woken up to a day with nothing scheduled, and wondered how I was going to fill it with something that both made life worth living, and also paid the bills.

In this conversation, I asked myself, How did you end up here? Have you made a big mistake? I had spent a good chunk of my retirement savings, left Silicon Valley in the midst of a boom, and now found myself barely getting by in South America.

About a thousand words in, I stopped and cracked into tears, not only because I was scared out of my mind, but because still — despite not seeing a clear path to making this work — I couldn’t see myself giving up. I concluded:

Take it from me, a ten-year veteran self-employed creator: If you are looking for security or reassurance, I do not recommend this line of work. However, if you are burning with curiosity — if your heart and intuition lead you to do things that don’t make sense — well, then you don’t really have a choice in the matter, do you?

When I was done with that conversation, I had a massive vulnerability hangover. I felt embarrassed to publish it, but since I had resolved to be writer, I felt I had to. However, I didn’t do anything I normally did to promote a post: no Medium publication, no email blast, no podcast episode, not even a tweet. I just quietly pressed “Publish” and got on with my day.

It slowly, then quickly, became the most popular thing I had ever written.

Now, five years later, I’ve been a full-time creator for fifteen years. (It wasn’t called that when I started. I was just a weird guy who wouldn’t get a job.) Not long after publishing my personal conversation, I started publicly reporting my income on my blog. While more famous bloggers were excitedly reporting six- and seven-figure months, I was…