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. 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 reporting one three-thousand-dollar month after another. One month I even lost money. However, about a year ago, my numbers started to climb. I recently reported a six-figure-year for the first time. I had made six-figures before the reports, but most of that was from an uninspiring blog I had written under a pseudonym. This was the first time I could look at every dollar I had made and say to myself, "I made this money doing exactly what I want to be doing. I am officially me for a living." I looked in the mirror later that day at the gray hairs that have come to dominate my beard and the stray ones sprouting from my temples. I thought back to when I was twenty-five and I'd stare in the mirror, looking at the young man I felt was full of potential, but who had no idea how to get out of Nebraska. Every cell of skin and hair on my body had regenerated since then, but I figured I still had the same eyes. So I looked into them and said, "You did it, kid. You made it." Not the next day, nor the day after that, but soon after, I felt a deeper emptiness than I had before. I thought back to my twenty-five year old self hearing for the hundredth time the CAD technician with hair as tall as the man was wide yell out, as he waddled through the break room, “Kadavy, with another Banquet meal!” Those microwaveable meals had been frequently on sale at Hy-Vee, ten for eight dollars, and the best strategy I could come up with in 2004 had been to save up and buy Apple and Google stock. As I had rolled my eyes and sighed at the Office-Space-like monotony of my existence, I would have gladly traded places with my current life. I had struggled for so long, so hard, and had passed up so many other opportunities a normal person would have taken. I risked failure, and hadn’t failed. Why did I feel a lack of inspiration, a malaise? Around that time, I read and resonated deeply with an essay by Joan Didion, where she marvels at how a six-month stay in New York crept into eight y