Buy yourself a job

Monetize your friends

When a friend of mine bought a gas station/convenience store in our small town, her father explained it as, “Well, she’s buying herself a job.” It sounded gruesome to me: long hours, low margins, and well-capitalized corporate competitors. But hey, it’s a small town and job options are limited. (Plus, she turns out to be great at it. Best product assortment you’ll ever see in a c-store!)

To me, making money on Substack feels like buying yourself a job. (Less capital outlay, so maybe building yourself a job.) You pledge to your customers that you’ll write X times per week. There’s no built-in vacation or sick time. Your renewal rates are based on your customers’ perceptions that their intellectual life benefits from your product. (It’s not like selling, say, appliances: when it wears out I need a new one.) Like many entrepreneurial ventures, there’s a ton of risk—yet unlike other forms of freelancing, there’s little flexibility. You’ve committed yourself to a weekly grind.

But hey, it’s the media industry and job options are limited. There’s an industrywide belief that mailing lists are valuable, and this is one of the few ways for an individual to monetize them. As one of Substack’s earliest missives advised me, “Bring your list from Mailchimp, TinyLetter, Patreon, and more.”

As a writer, I’ve never cornered a particular subject niche. (If I did, the businessperson in me would rather start a publication—an institution that I might later be able to sell—than a personal newsletter.) When I look at my tiny mailing list, I see relatives and friends. I am honored that they are willing to listen to my perspectives. To charge them for that privilege, to monetize that willingness, seems a bit crazy to me. To do so for the privilege of buying myself a job: doubly crazy.