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Fifteen Years as a Creator. (I’ll Never Make It.) – Love Your Work, Episode 283

July 14 2022 – 07:30am

Writing in my notebook, circa April 2009. (Photo: Ryan Halvorsen)

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.

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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.

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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 years, “with the deceptive ease of a film dissolve.” Young, foolish, and non-committal, she felt she “could stay up all night and make mistakes, and none of it would count.” It wasn’t until it was over she had realized, “it had counted after all.”

The dozenth friend said to me recently, “If you can sell 25,000 copies of a book, do you have any idea how much you could make on a course, consulting, or coaching!?” I politely explained I had heard the same many times before and I had tried courses, consulting, and coaching, and didn’t enjoy them. Basically, what I wrote five years ago:

I want to make a living creating. I don’t want creating to be merely a marketing strategy for other things. Is that completely insane?

This friend, like seemingly all I had at the beginning of this fifteen-journey, is now a millionaire. Did I feel this emptiness because it had taken so long to get here? Because there are many more definitions of “making it,” financially, beyond a six-figure income – that everyone else seems to reach so easily? I know every time I hear an outrageously popular twenty-something creator on a podcast say, “I wrote online for a long time before I had success. Like eight months,” I scoff and wonder, Just how fucking bad at this am I?

Maybe this six-figure milestone so close to my fifteen-year anniversary was just a reminder that it had all counted. Maybe it brings to the surface memories of the times I almost had a big break: Like the time I paid my own way to fly from Colombia to San Francisco to be interviewed on a massive podcast, only for them to can it. Or the time a big chest-thumping entrepreneur podcast didn’t run my interview because I openly told them how little money I made (given my public income reports, I wonder why they bothered inviting me).

Or, maybe I had failed at what I had actually wanted, but had invented a false goal ex post-facto, so what counted wouldn’t feel as if it had gone to waste.


I dug into the paper trail I’ve left throughout this journey. The stack of journals I’ve collected confirmed that this, indeed, was something I had wanted all along. In 2007, just before getting fired, I wrote, “I have lots of projects in mind, but the main one is making ‘being David Kadavy’ my full-time job.” There it was, plain as day.

As I continued my investigation into potential revisionist history, I re-read my conversation to myself after ten years as a creator, and saw a graph:

On New Year’s Eve, as 2008 turned to 2009, I stayed home by myself and schemed on my mission to make it as a creator. I knelt on the hardwood next to my portable radiator and drew this graph on an eleven-dollar piece of tileboard from The Home Depot. The plan was for “Active” income to give way to “Passive” income, to give way to “Speculative” income. In other words, I would freelance just enough to get by, build passive income on the side, and as that passive income built, I would follow my curiosity and see what I could find.

I had done exactly that: I had freelanced ten hours a week, made $150,000 on a passive income stream, and through the exploration I had done on the side, gotten my first book deal, then built this career as an author. I had followed my plan perfectly.

When a successful author friend had warned me not to write my first book – that there were better ways to make a living – I had reasoned I was just starting, maybe after ten years I’d be really good. In the back of my mind, I thought I could do it faster. Suffice to say, this has taken way longer than I had imagined.

Didion’s essay resonated with me because some part of me didn’t expect these years to count. At forty-three, with one parent gone, having narrowly-missed losing the other, and with my own body declining, I feel as if I’m in the final levels of a video game. I’ve gained power-ups and magic swords hidden along the way and in many ways feel more capable than ever. But that meter at the bottom of the screen marked “life” is lower, and I’m increasingly paranoid I’ll be devoured by a dragon before I storm the castle.


I ultimately realized, this emptiness wasn’t unfamiliar. I had felt it in some small way at every major milestone in this journey. With every goal I had achieved, there had been emptiness that followed the absence of that goal. That emptiness was soon replaced by the pursuit of the next. But, this was the top of the mountain. There was no next goal on the horizon.

Maybe I should feel bad for how long this has taken. Maybe I’m putting up blinders I won’t see around until it’s too late, and I’ll later be overcome by crippling regret. More likely, the journey is the destination. The beginning of each creative project is characterized by an emptiness, a void that must be filled through the act of creation. It’s a great feeling to go from spinning your wheels to getting traction, but ultimately, you want to go back to the starting line and do it again. To once more see if you can storm the castle.

You could argue I feel this way because this struggle is all I know. I’ve been at it so long, like Red and Brooks in The Shawshank Redemption, I’ve become “institutionalized.” But one got busy living and the other got busy dying, and as Victor Frankl has said, “What man actually needs is not a tensionless state but rather the striving and struggling for a worthwhile goal, a freely chosen task.”


So, after fifteen years, I’ve “made it” as a creator, financially-speaking, in a relatively minor way, for now. But maybe the best part of making it is realizing you now have the privilege of feeling you haven’t. So you can freely struggle to reach your destination, only to do it again.

Take it from me, a fifteen-year veteran self-employed creator: You’re burning with curiosity. Your heart and intuition lead you to do things that don’t make sense. You feel you have no choice but to take this path. But be forewarned: Once you get to where you so deeply ache to arrive, your journey won’t be over. You can “make it” in one way or another, but to be happy with this life, you must always find a way to feel you still haven’t.

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Theme music: Dorena “At Sea”, from the album About Everything And More. By Arrangement with Deep Elm Records. Listen on Spotify »

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