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Chloe Berger

Jon Stewart says David Letterman gave him the best career advice after his first talk show was canceled: 'Don't confuse cancellation with failure'

(Credit: SAUL LOEB / Stringer—Getty Images)

Most of us have been pushed and landed on our ass, instead of our feet, at one point or another. Of course, being callously told to throw your stuff in a cardboard box and leave lends itself to feelings of humiliation. But just because someone fires you doesn’t mean it’s the end of the road, at least if you take fellow late-night icon Dave Letterman’s advice to Jon Stewart to heart.

“They have locked the door and told me, ‘Get your shit and get out’,” Stewart told fellow comedian Larry Wilmore in 2016 during the final episode of Wilmore’s canceled late-night talk show, The Nightly Show. Stewart was talking about how some people in the entertainment world treated him after missteps in his early career. Back in the early 1990s, Stewart had a talk show of his own on MTV, aptly titled The Jon Stewart Show. He described it as a bit of a scramble as the show was bought by Paramount to replace comedian Arsenio Hall's. 

“I was the natural replacement for Arsenio. Because I think a lot of people are like, ‘Hey, the hip African American guy, let’s stick a maybe small Jew in his place and see what happens,’” Stewart said sarcastically on a recent Q&A at The Daily Show.

The Jon Stewart Show shuttered after less than a year. “We were all very sad,” Stewart said, explaining that “when your name is on it and they tell you to get out of the building, it’s very hurtful.” And nine months after its first airing, Letterman came onto Stewart’s last show to impart some wry words of wisdom. 

“He said to me: ‘Don’t confuse cancellation with failure,’” Stewart said. 

“I thought that was really interesting,” Stewart continued. “Then in the commercial break, he said, ‘Although… this is also a failure.’ He just didn’t want me to confuse it,” he joked. And Letterman was largely right. While the MTV gig itself might have not been a success, Stewart went on to reinvent the late-night comedy scene with a new form of political satire and commentary for decades at Comedy Central's The Daily Show. His defeat didn’t mean the end of his career.` 

Stewart imparted Letterman’s words to Wilmore when the latter was experiencing his own cancellation. “I took that to heart,” he said of Letterman’s quip, at the time.

Of course, not many of us are in the entertainment industry, so a one-to-one application of Letterman’s advice might be a little unhelpful. But the larger sentiment rings true as people, especially in the tech and media sector, experience layoffs. What might feel like the end of the road could amount to just a blip in it—much like the classic phrase from baseball player Yogi Berra, "It ain't over." 

Right now, the job market feels especially trying as even recruiters admit the process is arduous and long. But just because a boss has ushered you out the door, like Stewart, it doesn’t mean there aren’t greater things ahead. There’s always room to pivot for a better fit. 

“Regardless of your role at a tech company, your skills and expertise are valuable and can transfer to many other industries,” Sarah Doody, a future of work expert, told Forbes. “Just because your last job was at a tech company, that doesn’t mean you can’t get hired in another sector, and maybe even with a salary increase.”

Correction, May 22, 2024: An earlier version of this article misstated Larry Wilmore's surname.

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