Sometimes the Smartest Move Feels Like the Craziest
(and luckily I don't do things like this anymore!)
Comedy is full of risks. Getting on stage, hoping people like your material, booking the gig, getting to the gig—it’s all a gamble. But sometimes, just to spice things up, you add even more risk… on purpose.
Back in my comedy club road days, I booked a week of one-nighters—bar gigs across North Carolina, Monday through Sunday. I was starting to pivot toward corporate work, but at the time, I hadn’t lined up many of those gigs yet.
Then I got a call.
A company wanted me to perform for a Sunday noon event in Chicago—on the same Sunday as my last bar gig. And here’s the kicker: the corporate event would pay more than the entire week of one-nighters combined.
Now, I have a strict no-cancel policy—once I commit to a show, I don’t back out, no matter how tempting the money. But this time, well...
I didn’t cancel, but I did start researching flights. Sure enough,
there was a flight out of Raleigh, NC on Sunday morning, and one that would get me back in time that afternoon to drive two hours to my final one-nighter that night. It was a huge risk—counting on two flights in and out of Chicago on the same day? Yikes.
After a long chat with my bank account—and my better judgment—I took the plunge. Why?
A. I was transitioning into corporate work, and this Chicago gig could open doors. The one-nighters weren’t moving me forward.
B. If the booker got mad, I could return the Sunday gig money (or the whole week’s money) —and still come out ahead.
C. If the booker really got mad and never booked me again, I was
okay with that. I knew bar gigs weren’t my future.
D. The comic I was working with that week could cover my time if needed—and he’d be thrilled to get my paycheck.
E. Honestly, I’d be more upset turning down a great corporate opportunity just to perform for 50 half-interested bar patrons.
So I did the Saturday night show, caught a few hours of sleep, then
headed to the airport. I flew to Chicago, performed the gig (even as storms rolled in right before I took the stage adding pressure to me!), and dashed back to the airport.
The flight was delayed—of course—but we finally boarded. I made it back to Raleigh, drove two hours, and arrived at the gig an hour before showtime. Whew.
The other comic, who I’d been working with all week (we traveled separately),
casually said, “Hey, where were you today? I thought maybe we’d grab lunch.”
I laughed. “Chicago.”
He was floored. Honestly, so was I.
The bar show went exactly as expected: 50 people who weren’t really feeling my clean
comedy. But I had zero regrets—I’d backed the right horse. I’ve never done something that nuts again and don’t plan to in the future, but I stand by what I did.
Take calculated risks. If the downside won’t wreck your reputation, doesn’t leave anyone hanging, and helps you move toward your bigger goals, then maybe it’s worth the leap.
Jan McInnis is a Keynote Speaker, Comedian, Comedy Writer, and Master of Ceremonies. She has written for Jay Leno’s Tonight Show monologue as well as many other people, places, and groups – radio, TV, syndicated cartoon strips, and even guests on the Jerry Springer show (her parents are proud). For 20+ years she’s traveled country as a keynote speaker and comedian sharing her unique and practical tips on what business leaders can learn from comedians (no, it’s not all about telling jokes). She can be reached at www.TheWorkLady.com, or Jan@TheWorkLady.com She’s also a GREAT Master of Ceremonies. Click here for her emcee site
Some of the stories in this newsletter are taken from Jan’s popular book:
Convention Comedian: Stories and Wisdom From Two Decades of Chicken Dinners and Comedy Clubs.