The Dark Side of Running a Paid Newsletter
Peep Show: Issue #1
Peep Show is a semi-regular series where I go full Hemingway.
"There is nothing to writing. All you do is sit down at a typewriter and bleed."For over 10 years, I’ve made money by writing.
I retain some skepticism about the whole deal. Sort of ‘how is this even possible,’ but also ‘how much longer can I possibly bewitch people with Star Wars inside baseball and penis metaphors.’ It’s like a dream I’m cognizant of having, one I expect to wake up from any moment.
But an interesting thing happens after people start putting money directly in your pocket because they like your work.
After the ‘holy crap’ euphoria faded, it slowly dawned on me that, in a sense, I work for my paid subscribers. I doubt any of them see it that way. Doesn’t matter. That’s how I feel about it. It’s not quite obligation. It’s more like a desire to prove their instincts right. They bet on the right horse.
Such thoughts sent me into a bit of a tailspin.
Imposter syndrome is like Syril Karn’s mom in Andor—it has nothing positive to say but is super hard to ignore. (Syril is the sociopath who moves back home and eats cereal while his mom busts his balls.) Mine flared up after a holiday break that wasn’t much of a break. Worse, I didn’t make any progress on the Star Wars book, which just made me feel even more impostery. I’ve been grappling with emotions—doubt, guilt, and shame, the unholy trifecta—ever since.
My grandma collected a lot of ailments toward the end of her life, conditions which required regular visits to the hospital for surgical procedures. She once told me, “getting old isn’t for sissies.” I’d like to borrow her colorful inflective.
Going paid isn’t for sissies.