Dennis Hensley on Going from Landing a Book Deal to Working at Crate & Barrel (And Everything in Between)

2025-12-02

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Dennis Hensley was the very first real writer I ever knew—back when getting a book published felt like spotting a unicorn in 1990s LA.His debut novel Misadventures in the (213) came out in 1998, and I thought it was the coolest thing imaginable.Years later, we'd find ourselves sweating through Ben Allen's dance classes together, proving that creative people really do wear all the hats.Dennis has written for everyone from Joan Rivers to Wondery podcasts, created party games and somehow made more money dancing in commercials than writing this y...

Dennis Hensley was the very first real writer I ever knew—back when getting a book published felt like spotting a unicorn in 1990s LA.

His debut novel Misadventures in the (213) came out in 1998, and I thought it was the coolest thing imaginable.

Years later, we'd find ourselves sweating through Ben Allen's dance classes together, proving that creative people really do wear all the hats.

Dennis has written for everyone from Joan Rivers to Wondery podcasts, created party games and somehow made more money dancing in commercials than writing this year.

Our conversation (recorded the day before his 61st birthday) goes deep on resilience, disappointment and figuring out how to keep creating when the scoreboard stops making sense.

Topics Discussed:

The 1990s writing gold rush: When Gen X believed you could actually make a living as a writer, gift bags overflowed at parties. and magazines paid $1 per word
Breaking in: How an audition rejection for Madonna's Blonde Ambition tour became Dennis's first published article, leading to gigs at Movieline, Detour and beyond
Writing for free (for three years): The unglamorous hustle behind Misadventures in the (213), including interviewing Carrie Fisher in her bed and scoring a gym membership through barter
The 2013 Fashion Police strike: How standing up for freelance writers' pay during the Writers Guild organizing effort traumatized Dennis, cost him his best friend/roommate and triggered a health crisis that changed everything
Rehab for disappointment: Dennis's raw account of hospitalization, thinking he'd "die of disappointment" and the long road through somatic therapy, meditation and redefining success
Changing how you keep score: Why tracking wins vs. losses will destroy you, and how Dennis learned to measure creative life by "who I'm being" rather than what he's getting
The game that almost was: Pitching "You Don't Know My Life!" to Jason Bateman's production company, feeling good about the pitches, getting rejected—and being sad for only five seconds
"Everything is impossible, so anything is possible": Life lessons from artist Stephanie Elizondo Griest and why trying matters more than outcomes
Dancing pays better than writing: How Dennis made more money this year from Vegas commercials than his writing career, and why he's okay with that