Indentured & Independent: Freedom and Fatigue in Gig Life

Deep Dives in the Shallow End

In this episode of Deep Dives in the Shallow End, we put hustle culture on blast and offers a heartfelt “thank you” to the gig economy…for our daily existential crisis. From recording in his hatchback en route to sell plasma (for the rent), Donovan navigates the wild, soul-crushing world of modern side hustles. Think freelancing is freedom? Think again. We’re talking endless rideshare shifts, grocery gigs, and desperately avoiding that feet-pic hustle—for now.

With dark humor, painfully relatable anecdotes, and some brutal truths, we break down what it’s really like to be an “independent contractor” in a world where burnout is a badge of honor, “self-employment” means zero benefits, and sleep is for the weak. Tune in for a laugh, a reality check, and maybe a light cry as we explore if the dream of “being your own boss” is just another way to clock in...forever.