The Side Hustle Secret
🌟Career Coaching: A reliable income stream changes everything when you're in the entertainment industry.
When I first landed in New York City from Michigan—what feels like a dozen lifetimes ago—I arrived armed with big dreams, a one-month sublease on a studio apartment that came with a roomate, and the kind of blind optimism that only a twenty-something can possess.
I took every job imaginable to keep myself afloat. The most memorable? Four slapstick hours as a waiter, nervously ferrying fried flounder dinner specials from the kitchen to the dining room—until a tray full of them hit the floor in one spectacular, greasy crash. At that point, the owner handed me $20 and showed me the door.
But the real problem wasn’t my inability to carry fish on a tray—it was the constant anxiety of not knowing where my next paycheck would come from. I moved to NYC convinced I would write the next great American drama, only to realize that loving the city’s energy meant I couldn’t stand to stay home alone and write. (Ah, the siren song of Lower East Side.) And also—Virginia Woolf was absolutely right!—I couldn’t have a creative life without £500 a year and a room of my own.
Creativity Demands Breathing Room
Back then, I thought that hustling meant suffering—that scraping by was just part of “paying dues.” I saw peers in the industry cycling through endless gigs, hoping that the next one would finally mean stability. But for most of us, the cycle never seemed to break.
What big lesson did I learn? Chasing every dollar is exhausting. And relying solely on project-to-project income leaves you perpetually on edge, unable to immerse yourself in your creative work because you’re constantly haunted by the specter of next month’s rent.
At the end of the day, creativity requires the freedom to take risks. You can’t invent new narratives, imagine groundbreaking solutions to producing challenges, think outside the box, go for gold, reach for the skies—or whatever your preferred cliche—when you’re stressed about money all the time.
The Side Hustle Revelation
It took me longer than it probably should have to see the pattern. I finally realized that so many people who thrive in the entertainment industry—the ones who actually advance their projects and careers in a sustainable way—have at least one of three things: 1) a trust fund, 2) an industry-connected family member, or 3) a side hustle. Most of us don’t have 1 or 2, and neither are something we can control.
But having a reliable stream of income that is not dependent on one employer or one creative project is something everyone can achieve. A successful side hustle is not dependent on the family you’re born into.
Side hustles don’t have to be soul-crushing. In fact, they should bring you some joy. I’m talking about a business you can keep running whether you’re prepping a shoot, rehearsing a play or attending a festival. I know a writer who makes fabrics, an actor who runs a fleet of ice cream trucks and a musician who handles taxes for fellow artists. I know producers who fund their projects by selling merchandise and directors who are landlords. The possibilities are endless.
And here’s the amazing part: once I had that steady foundation, every part of my creative world opened up. I could take on riskier projects, build genuine connections without the desperation of needing a job, and pitch my ideas and projects with confidence—because I wasn’t coming from a place of scarcity. I was finally building real momentum, not just treading water.
If you’re still feeling stuck between creative ambition and financial instability, know that you’re not alone and it’s not your fault. Most people never talk about the real day-to-day grind behind the “overnight success” stories in our industry.
But you can change it by creating a side hustle that makes sense for you. Because you deserve to be more than just “surviving” in this industry.
You don’t need a trust fund or a cousin at CAA. You just need a plan that works for you. Start small. Start weird. And don’t wait for someone to hand you permission.
Your insights and writing style is so wonderful! Thank you!