My only creative strategy/business plan is deadlines

(and most of them are fake)

[NOTE: This is a post I created for Patreon supporters, so I’m publishing it here for paid Substack subscribers as well]

About 20 years ago (OK, 22 years ago), I really wanted to make it as a freelance writer, despite all the warnings about how difficult it was. When I was in grad school at the University of Montana trying to get a master’s degree in journalism, I became friends with a guy named Jed who was a year ahead of me in the program. Jed went on to become the music and theater critic at the Boston Herald for 10+ years, but 22 years ago, he was freelancing, and unlike me, getting articles published and getting paid.

We were talking on the phone, me standing in my apartment in Scottsdale, Arizona, where I was struggling to pay half the rent with my then-girlfriend. Jed was in Boston, where he’d moved after leaving Missoula around the same time I did. He mentioned that he’d written a piece about skiing for an airline magazine, which sounded like it paid very well. But I didn’t know Jed to be a skier, so I asked, “Wait. Do you ski?” To which Jed said,