I’ve been working in comedy clubs and the entertainment world for over 20 years. Every year, I’d witness a few artists break through—they’d make their mark on a late-night show, suddenly they’re touring the country, performing at colleges and clubs, and making it big. Or every so often, you meet a new me, someone who figured out how to thrive in the corporate and educational production game.

These artists live the life 24/7. They write, they perform, they constantly create content for their feeds, and they relentlessly find ways to get paid for their work. They hustle in the clubs. They realize the grind is substantial, but it’s still infinitely better than any day job.

And then there are the thousands of comics and actors who pop in from time to time. They treat art like a community theater activity, devoting just a few hours a week. They take classes for the right to perform for free.

The Joy of the Hobbyist

Now, for those without ambition—the thousands doing comedy and theater purely for fun, treating it like a community center—I offer no judgment. In fact, I’m genuinely jealous of you! You get to do this JUST for the love of the stage.

But I think folks come to town from around the world, and they see a couple hundred artists working on Broadway and in New York City’s clubs. Then they see the thousands of folks performing for free—the educational and showcase comedy and theater. Very few witness that crucial in-between stage: the hustle, the less fun parts of our world.

That part is a lot less fun, unless you do what I do: turn it into a game. You have to love the process, the game, as much as the final stage time. I daily say I don’t have a real job, but I am 20 years day job-free because I treat the business like a job. I just have so much fun it rarely feels like work.

The Trap of Unpaid Work

Nothing makes me sadder than when I try to give someone PAID work, and they are unavailable because they committed to unpaid “work.” They then have to get up early and go to their actual day job. They accept this cycle as the norm.

Truth be told, so did I for three years. When I got to New York in 1997, I was offended by the expectation to perform for free, to “showcase,” or worse, pay to perform. I was good on stage, but my mediocre audition routine had only worked in the small pond of college. So I spent three years in restaurants barely auditioning, hardening myself with 60-hour workweeks and late nights, with nothing to show for my artistry.

It took about eight years to fully figure it out, finally quitting my last boss in 2005. The transition began when I started respecting the business. I stopped being the big fish from the small college pond and became the artist who needed to make my own way, swimming against the current in the big ocean.

The Moment of Clarity

In 2005, my team and I were self-producing four shows a week at the NY Improv. We met dozens of working comics—big names from the 90s, up-and-comers hustling for stage time, and dozens of ROAD DOGS—the less famous, unknown working comics hustling gigs around the country. We also met hundreds of wannabes who no longer work.

My success over the last 20 years was realizing the biggest difference in that moment. Every time I saw a colleague make their late-night debut, I could imagine the hundreds of nights I saw them in the club, getting on stage 20 times a week or more. Every time I heard someone complain, “Why them, not me?” that person was doing one show a week.

Again, no judgment. Everyone has bills and a life to live. But the one consistent factor in successful artists? None of them were discovered while at their day job or sitting at home. They weren’t discovered at all. They meticulously built an act and a network. They came to play, to give their best, and chose to be the folks people wanted to work with. I’ve never seen anyone get “LUCKY.”

“Bad luck” in our business is a product of ego and insecurity, laziness, or far too often, substance abuse. I’ve never heard a hustler complain about “nepo babies.” They celebrate every time another breaks through. They are tenacious, and they find a balance between SHOW & BIZ.

The Illusion of Luck

Someone who knew me recently found out I had TV credits and said I got lucky. NOPE. I was hustling at the NY Improv for six months, selling out shows on Sundays and Mondays. The club manager got a call on a Monday afternoon from MTV: “Do you have any fat guys with a hairy back?” Eric came upstairs and asked me, “Busy tomorrow?”

Small minds will call that luck, being in the right place at the right time. That thinking offends me. I paid my dues. I was in the right place because in those days, I was rarely home on the couch.

Suddenly, I was Walt Frasier from MTV. Within the next year, I got a call from Letterman. “Can you be here in an hour for a costume fitting?” I had sent postcards to every casting director in town. It wasn’t luck; it was a domino effect of earned credit.

If you truly want to be a working artist, watch and learn from those that are working. Ignore the advice of those at your day job or unpaid shows. They haven’t figured it out.

Always Be Creating (and Monetizing)

When a young artist shrugs and says, “But you love marketing…” I simply retort, do you love side work after eight hours of serving food and drinks?

Everything I do, for the past 20 years, markets everything else I do. Every minute of “work” goes towards developing my art OR finding ways to monetize my art. Every social media post, every client call/email, every audition is a step toward paying my bills with my talent.

I can’t guarantee paying your dues will pay off. But I can guarantee: those that chose not to do the work, don’t make it.

Always be creating. ALWAYS BE CREATING! And then, you have earned the right to complain about luck. But chances are, you’ll be too busy having fun.