Photo Source: Hanna Barczyk

Failure is funny. And if your goal is to make people laugh, you should hope that it happens to you often.

When I first started doing comedy, I enjoyed getting laughs, but there was always a part of me that also wanted to look cool. Whether it was the nonchalant way that I conducted myself onstage or the pseudo-rock star–looking promotional photos I had, there was always this youthful part of me that was terrified of being laughed at for the wrong reasons.

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Ironically, when I was offstage during this time, I would unintentionally crack up my close friends and colleagues by telling them horror stories about my embarrassing real-life failures. These stories could be about a terrible business blunder I had made, or perhaps how I put my foot in my mouth during an important meeting. They were personal anecdotes that I would never want the world to know about, lest people think I was stupid or clumsy. And my friends would laugh. Hard. I would argue harder than any audience had ever laughed at my stage act. These stories were resonating with my fellow performers so much that I started becoming known among my peers as a “born to lose” character. And still, the stories accumulated. How strange it was, looking back, that my job title was “comic,” and yet most of the laughs were happening when I wasn’t working.

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What I wish someone had told me earlier is that failure is one of the best assets a comic can have, and to try to conceal it is contrary to the very thing you’re trying to do. Failure is comedy in its purest form. Audiences don’t watch a comedy film about a police detective who does the job with great competence, nor do they pay to see a clown whose pants stay on and fit perfectly (unless the clown is expressing failure at being a clown, which I guess is a loophole). Generally speaking, we laugh when we see someone who is worse at life than we are.

This is not to say there are no “cool” comedians. It’s pretty hard for me to look at old footage of Lenny Bruce smoking a cigarette and not see elevated levels of coolness. But comedy is about exposing human foibles, whether you’re revealing them in others or divulging them about yourself. Personally, I like when it’s a combination of both. When I finally came to this realization, I had a cathartic outpouring of content depicting my vast array of life failures—and there were many: botched romances, embarrassing social flubs, dumb career choices. Suddenly, the general audience was being let in on secrets that had previously been known only by my closest friends. And for the first time, I started feeling like an individual voice was emerging in what I was doing. Most importantly, the laughs were bigger. So my advice, whether your dream is to be a comic or maybe you’ve just been assigned a comedic role and it’s a huge departure for you, is to remember this: The more you hold on to trying to look cool, the less chance there is that what you’re doing will be funny.

Phillips is an L.A.-based comedian. He can be seen in “Punching Henry,” an indie film he wrote and stars in alongside Sarah Silverman, Tig Notaro, and J.K. Simmons. He’s also appeared on “Silicon Valley” and “Drunk History.”

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