The Freelance Creative

‘You’re Going to Bomb’: 5 Freelancing Lessons from a Standup Comic

Since 2007, I’ve captained my own freelance career ship. Some days have been more Jolly Roger, while others have been more Titanic. And after braving the seas of freelancing for seven years, I decided to take on another arena in the gig economy: standup comedy. When deciding how to spend my nights, it was either that or medical school, but standup won out.

Here’s the truth: Medical school would have been less terrifying.

Here’s another truth: Freelancing has made me a better comic, and standup has made me a better freelancer. Here are five parallels between freelancing and standup that may help you find the funny in this gig economy.

1. You’re going to bomb

And by that, I mean I bomb. Regularly. And it’s not because I suck. It’s because I’m learning. I had an incredible instructor in my first standup class who opened with, “You’re going to bomb. Get used to it. And it’s awesome.” And he was right. Each time I bomb, there’s a lesson to learn. It’s not unlike when I launched my freelance writing career—I had more swing-and-misses than I did grounders (forget about home runs). We practice to get better. A well-honed freelance practice comes from writing drafts, bombing, and rewriting. Just like standup.

2. About that paycheck…

Every bit of standup I’ve done thus far has been for free. I have friends performing for a cut of the cover charge and others making between $50 and $100 per night on bigger showcase gigs. Why do we do it? Because we love it, we’re gluttons for punishment, and it’s a necessary grind to build a career. Whether telling jokes or writing blog posts, you’ll likely start off with a pretty low rate. Remember that passion when you’re staring at 10 bowls of ramen each week.

3. Write it down

I carry this bound purple notebook with me everywhere. It’s my idea book. Should I ever get hit by a cab and my body is found in the streets of Chicago, this purple notebook will be with me. The cops will flip through it, question why I’m not in a mental institution, and have a laugh. I write down everything that might be funny, and the good stuff gets funnier with work and time. The same idea carries over to freelancing when I’m brainstorming new topics and people to interview. I can’t tell you how often I find joke ideas or article concepts when I go back through my notebook. And maybe I should think about investing in a separate notebook, for times like this, when I’m freelancing about standup. See how it all comes together?

4. Meet and greet

Standup comics get bigger and better gigs by getting recognized over time at open mics and supporting other comics—that’s a huge part of building my career in standup. I wish more freelancers thought like standup comics rather than brooding over a laptop. Devoted comics talk to other comics; they talk to show hosts. They’re an asset to the room whether they’re holding the mic or not. Your freelance business depends on the quality of your work, but it also hinges on the relationships you’re willing to nurture.

5. Take the time to find your rhythm

While I don’t think I’m going to wake up one day and be Ellen DeGeneres—though that would be grand—I go through some natural frustration as I try to find my voice. It’s going to take time to align my style and talents with the clients and audiences that would appreciate them most. A joke will go over one night and fall flat the next day. I wish I knew why, but it happens. I’ve occasionally found that a particular crowd isn’t picking up what I’m putting down. Sometimes, I have to find a new audience. Just like I’ve had to find new clients and readers over the years for my writing.

The worlds of standup and freelance writing intersect more than you might think. Everyone’s funny in front of a bathroom mirror, and we all think we’re worthy of a Pulitzer when we put the final period on a first draft. However, what really binds both worlds is how the hustle never stops.

The good news? No student loans from medical school.

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