Lately, I’ve been dealing with a near-crippling loss of interest in my own freelance writing. I’ve kept going, as one does, because it amounts to a few thousand extra dollars a month for work I can do from the comfort of my home office.1

After 15 years, it’s hard to keep generating fresh or unusual topics — and doing so is essential for an “out-of-cite” figure like “ya boi” here. This is because my stubborn refusal to pander by writing the same content over and over for an audience of parasocial simps and haters has meant that I’ve had to keep reinventing myself and my work simply to bring in the do re mi for the our savings account. Each article written in this fashion lives or dies on its own merits2, and each “blank page problem” is another puzzle to be solved.

Honestly, I’m staggered that this publication generates $400-500 a month3, yet also chagrined that it isn’t far more.4 Based on my own market projections, I can’t imagine selling anything to publications well past 2025 — and even that is quite late, especially given the rapid progress of AI-generated work — so it’s incumbent upon me to justify the perpetuation of the creative output that’s most meaningful to me.

Thus, I’ve decided to republish and expand this article, which appeared in the Columbia Journalism Review more than a half-decade ago.5 At the time, I was dealing with a crisis of faith6, pondering my gradually-diminshing workload in publications such as VICE and The Atlantic while listening to Mickey Newbury’s “Nights When I Am Sane” and Johnny Paycheck’s “The Old Violin” on repeat.7

After it appeared, business picked up, even if much of that work is forgotten or memory-holed8: I landed the obituary beat at the Ringer, I labored on a podcast worth $3-4k a month9 after leaving a similar administrative role at Payday Report, I discovered a number of other regular outlets, and I started climbing the actual 9-to-5 corporate ladder from the aforementioned comfort of my home office.

Alas, all of this is slowing down once again, even if I’ve improved as a writer and developed a better understanding of what I do and don’t want to do with my work,. Thus I’ve reached another impasse. What does the future hold? I suppose it’s impossible to say; my upbringing was so chaotic that the brute beast in me is happy merely to be “sucking wind for another 48,” as my father would put it, content with little more than “two hots and a cot.” It is only for my daughter that I worry, but I worry ceaselessly.10 How much longer, I wonder, can I live the creative life “sin vivir en mí,” in the words of Teresa of Ávila? Yet one must keep making moves until they’re all out of moves.11