Jon Stewart on Letterman's Advice: "Cancellation Isn't Failure"

Exploring Jon Stewart's journey through career challenges and triumphs

by Zain ul Abedin
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Jon Stewart on Letterman's Advice: "Cancellation Isn't Failure"
© Jamie McCarthy/Getty Images

Jon Stewart once shared some of the best career advice he received from none other than David Letterman, during a period of significant professional uncertainty. After Stewart's early talk show was canceled in the 90s, he found solace and perspective in Letterman's words during his final show.

"Don’t confuse cancellation with failure," Letterman told him, a piece of advice that has resonated deeply with Stewart over the years. The backstory to this advice dates back to when Stewart was hosting "The Jon Stewart Show" on MTV, which was meant to fill the void left by Arsenio Hall.

Despite the mismatched replacement, as Stewart humorously noted, the show was short-lived, lasting less than a year. During his last episode, Letterman appeared as a guest and imparted the memorable advice. Although he humorously added, "Although...

this is also a failure," during a commercial break, the main takeaway was clear and impactful. Stewart's early career in television was fraught with challenges and setbacks. After his show was abruptly canceled, he described feeling a profound sense of personal failure, especially painful given his name was prominently associated with the show.

However, Letterman's advice helped him to differentiate between a project’s end and personal defeat.

Stewart's Transformative Resilience

This lesson proved invaluable as Stewart went on to revolutionize late-night television with his next venture, "The Daily Show." His approach blended political satire and comedy in a way that redefined the genre and made an indelible mark on TV history.

Stewart's resilience and ability to pivot from his earlier setbacks underscored the truth in Letterman's words. The relevance of this advice extends beyond the entertainment industry, resonating particularly in today's volatile job market, where layoffs and cancellations are commonplace.

For many, especially in sectors like tech and media, what might seem like a career-ending move can merely be a transition point. The ability to adapt and redirect one’s path in the face of change is crucial. Experts like Sarah Doody, a future of work specialist, echo this sentiment, emphasizing the transferability of skills across different industries.

Regardless of one’s last position, the potential for new opportunities remains vast, often with the possibility of better alignment and even salary improvements. Thus, the wisdom shared between two legendary television hosts carries a powerful reminder: a setback need not be the end but the beginning of a new chapter.

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