• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia
SuccessJon Stewart

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

By
Chloe Berger
Chloe Berger
Down Arrow Button Icon
By
Chloe Berger
Chloe Berger
Down Arrow Button Icon
May 22, 2024, 2:56 PM ET
David Letterman once imparted some of Jon Stewart's greatest advice.
David Letterman once imparted some of Jon Stewart's greatest advice.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.

Recommended Video

“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.

Join us at the Fortune Workplace Innovation Summit May 19–20, 2026, in Atlanta. The next era of workplace innovation is here—and the old playbook is being rewritten. At this exclusive, high-energy event, the world’s most innovative leaders will convene to explore how AI, humanity, and strategy converge to redefine, again, the future of work. Register now.
About the Author
By Chloe Berger
LinkedIn iconTwitter icon
See full bioRight Arrow Button Icon

Latest in Success

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • Future 50
  • World’s Most Admired Companies
  • See All Rankings
Sections
  • Finance
  • Leadership
  • Success
  • Tech
  • Asia
  • Europe
  • Environment
  • Fortune Crypto
  • Health
  • Retail
  • Lifestyle
  • Politics
  • Newsletters
  • Magazine
  • Features
  • Commentary
  • Mpw
  • CEO Initiative
  • Conferences
  • Personal Finance
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
About Us
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map

Latest in Success

Larry Page looks up and to the right.
InvestingBillionaires
Jensen Huang might be fine with a billionaires tax, but Google cofounder Larry Page is already dumping California
By Sasha RogelbergJanuary 7, 2026
19 hours ago
walz
PoliticsMinnesota
Walz in the wilderness: from future VP to unemployed in just a few years
By Steve Karnowski and The Associated PressJanuary 7, 2026
21 hours ago
Ted Sarandos
Successlifestyle
Netflix co-CEO says he doesn’t read business books—at all. Instead, he reads one 1902 fiction about a ship and its reckless ‘hot dog’ captain over and over again
By Preston ForeJanuary 7, 2026
22 hours ago
Lonely young woman in office
SuccessWorkplace Wellness
Staff at a major Swedish pharmacy chain are being paid to take time off with friends to combat loneliness—they can even text loved ones during the $100 ‘friendship hour’
By Emma BurleighJanuary 7, 2026
22 hours ago
fraser
CommentaryLeadership
The 7 most overlooked CEOs in 2025—and the 5 to watch in 2026
By Jeffrey Sonnenfeld and Stephen HenriquesJanuary 7, 2026
1 day ago
SuccessThe Interview Playbook
Gen Z’s hiring nightmare is real. These are the curveball questions CEOs are asking to catch out job seekers: ‘Design a car for a deaf person’
By Orianna Rosa RoyleJanuary 7, 2026
1 day ago

Most Popular

placeholder alt text
Law
Amazon is cutting checks to millions of customers as part of a $2.5 billion FTC settlement. Here's who qualifies and how to get paid
By Sydney LakeJanuary 6, 2026
2 days ago
placeholder alt text
Economy
Mark Cuban on the $38 trillion national debt and the absurdity of U.S. healthcare: we wouldn't pay for potato chips like this
By Nick LichtenbergJanuary 6, 2026
2 days ago
placeholder alt text
Future of Work
'Employers are increasingly turning to degree and GPA' in hiring: Recruiters retreat from ‘talent is everywhere,’ double down on top colleges
By Jake AngeloJanuary 6, 2026
2 days ago
placeholder alt text
Personal Finance
Janet Yellen warns the $38 trillion national debt is testing a red line economists have feared for decades
By Eva RoytburgJanuary 5, 2026
3 days ago
placeholder alt text
Success
MacKenzie Scott sends millions to nonprofit that supports anti-Israel and pro-Muslim groups, two of which are facing federal probes
By Sydney LakeJanuary 6, 2026
2 days ago
placeholder alt text
Personal Finance
Current price of silver as of Tuesday, January 6, 2026
By Joseph HostetlerJanuary 6, 2026
2 days ago

© 2025 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.