Garry Shandling and the art of being a quitter

Throughout his life, the comedian repeatedly made difficult decisions to abandon jobs, even good jobs — even great, once-in-a-lifetime jobs. It served him well.

Adam Grybowski
3 min readApr 18, 2018

Garry Shandling had no problem being a quitter.

Throughout his life, he repeatedly made difficult decisions to abandon jobs, even good jobs — even great, once-in-a-lifetime jobs.

As a college student, he quit studying electrical engineering because he couldn’t conceive of working as an engineer. He switched to marketing, and because he found it a less demanding subject, he had time to fool around with writing comedy. He wrote several scripts for television shows (Sanford and Son, Welcome Back, Kotter) and despite the success, he chose to quit and pursue stand-up comedy.

Shandling became famous as a comic, and he soon accomplished his goal of appearing on The Tonight Show with Johnny Carson. Next, he wanted to become a late-night host. He worked his way up to become a regular guest-host on The Tonight Show, and just when his dream was close to being realized, he swerved and decided to create a TV show instead.

Those decisions were borne out of a desire not for material success or comfort or ego satisfaction but rather the wish — the need — to be true to himself. In The Zen Diaries of Garry Shandling, Judd Apatow’s insightful and affecting documentary, we repeatedly see Shandling searching for the truth of his authentic self. He seemed to believe that the more he could be himself, the more successful he would be and the happier he would be. He was driven by that belief.

“Be Garry,” he writes over and over again in his diary.

To find his authentic self, Shandling refused to be complacent. He approached each step of his life by questioning if it would help him grow. When he was deciding to accept the job as David Letterman’s replacement on Late Night or create a new sitcom, he asked himself, “Can I grow as an artist going on TV every night?”

He went on to create two groundbreaking shows, It’s Garry Shandling’s Show on Showtime and The Larry Sanders Show on HBO. Shandling approached other projects with the same need to push the boundaries of his self and the art form. Even when it came time to produce the DVD extras for a best-of Larry Sanders Show package, he created a highly unusual exploration of the show and its creators that critics judged as interesting as the show itself.

The constant self-scrutiny came at a cost. Conan O’Brien observed that Shandling was “enveloped in self-criticism,” and that condition could at times be unhealthy, especially as Shandling got older. Apatow’s documentary revisits an uncomfortable appearance on Conan’s Tonight Show when Shandling seems to be criticizing his performance in real time, his self-awareness in overdrive.

But overall, Shandling’s willingness to look inside himself served him well, even when it led him to decide to walk away from safe prospects. Quitting is often viewed through the lens of failure, of giving up, but Shandling’s life shows how the choice to quit can be brave and lead to growth and fulfillment.

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