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Whitney Cummings Fearlessly Transmutes Failure Into Success

Whitney Cummings is famous for making failure her bitch.

After working for more than fifteen years in the world’s of comedy and entertainment, Cummings has written, directed, produced and starred in movies and TV shows, released several comedy specials, appeared in comedy roasts, talk shows, and has ultimately been able to shape a career reflecting her blunt feminist perspective.

She recently premiered her podcast, Good For You, where she interviews celebrities, comics, and friends, and also released her fourth comedy special Can I Touch It? on Netflix. Oh, and she’s just joined a new social media platform called Tik Tok, which may or may not be on its way to replacing Instagram in social media popularity.

“I don’t believe in failure. I just don’t think that’s a real thing, because it’s all practice.”

Given just how much Whitney has helped shift the conversation around how women can and should behave in public (and onstage) it’s not surprising she’s been met with her fair share of pushback, criticism, and failure along the way. Fortunately for us, none of this has slowed her down. “I don’t believe in failure,” Cummings explained in a recent interview following her appearance at Patreon Assembly, a summit focused on celebrating the creative class. “I just don’t think that’s a real thing, because it’s all practice.”

“Maybe because I’m a comedian and we sublimate all ostensible failures into jokes,” she continued. “But very early on I realized: ‘Oh my god, my mistakes and my failures are… going to pay for my mortgage.’” Cummings said that she views mistakes as something she can “alchemize into art,” and points out the best stories usually involve the process of transforming disasters, catastrophes, and nightmares into something bigger and better.

”Oh my god, my mistakes and my failures are going to pay for my mortgage.”

In conversation with comedian and actor Paul Scheer at Patreon Assembly, the two comics — who initially met in the pre-social media era while working together on shows for MTV and VH1 in the early 2000s — discussed how being able to connect directly with fans has empowered creators and changed the entertainment industry.

Getting excited over the new wave of social media brilliance that’s cropping up on apps like Tik Tok, when asked if she had any regrets or about the arc of her career, Cummings admitted she wished she’d embraced technology more seriously years ago, and taken advantage of how new platforms let creators directly connect with their fanbase. “I wish I had just done a podcast sooner,” Cummings said. “I wish I had taken Instagram serious sooner. I wish I had taken what I thought were ephemeral social media fads seriously sooner. I wish I had spent more time connecting with fans one on one instead of trying to impress networks.”

“I wish I had spent more time connecting with fans one on one instead of trying to impress networks.”

Still, it’s not like Cummings didn’t fare well when working with networks, too. A huge part of her success was due to creating the CBS sitcom 2 Broke Girls back in 2011, which ran for six seasons all the way through 2017 and put her on the map as not just a comic or an actor, but a producer. In the end, though, some of her most meaningful work as a creator has come not from creating fictional stories but telling the story of her own life — whether it’s on stage or in a different format.

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“It took me five or six years to even say something true on stage,” she said. “I thought I had to like, write jokes, and although that was a style that I admire and love and find really funny, it wasn’t something that wore really well on me. So it took me a while to figure out what I was going to talk about on stage.”

“It took me five or six years to even say something true on stage”

And still, the ghosts of failure, criticism, and disaster can loom around any corner, perhaps resonating even more painfully for creators like Cummings who work from a personal place — that’s just part of the cycle of risk and reward that all creators face. But particularly as a woman, Cummings wants to highlight how the playing field is still gendered in a way that impacts every single industry, every facet of public life. It isn’t just female comics who face heckling and harassment, or just in entertainment that it’s tough — it’s everywhere.

“I think it’s just hard to be a woman in every field, all the time,” she said. “I don’t think being called a whore, or told you look old, or you’re busted or asked why don’t you have kids and why aren’t you married — unfortunately, I think all women have to deal with that — not just the ones that are telling jokes onstage. I don’t want to minimize all the women in every field who have to go through it by saying it only happens to me because I talk to strangers at night with a microphone.”

Even after realizing that her own life experiences were something that resonated with a lot of other people in the world — especially other women — some of the subject matter she wanted to discuss was still a little difficult for Cummings to address. Learning how to shift modalities when it came to different kinds of material, and trusting that audiences would be open to that, is something about the current creative era she’s grown to appreciate.

Along with her recently launched podcast, she’s previously written two books — Emotional Ninja in 2013, and I’m Fine… and Other White Lies, published in 2017 — and these more removed creative formats, in particular, allow her to tackle potentially volatile issues.

“There are a lot of things I wasn’t comfortable talking about as a standup onstage,” she admitted, “but I was comfortable putting in a book. I talked about addiction, I talked about codependence, I talked about sexual assault. That’s something that onstage I just couldn’t get comfortable with for some reason. And on my podcast, I can do it, and in a book, I could do it, so I think that I’m so grateful that there are so many ways to be creative now.”

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