Jon Stewart’s Best Career Lessons

Last week Jon Stewart flicked off the lights for the last time at The Daily Show, where he and his staff created a machine that delivered incisive political and media commentary through comedy for 16 years. Let’s take a look at how they did it and what we can learn.

Photo by Martin Crook. Contact the author at [email protected].

Surround Yourself With Great People

In discussing the inner workings of the show, the always self-deprecating Stewart has been adamant about one thing: the staff of the show are what make it great. From the producers and interview bookers to the writers, a daily talk show requires a small army to function. Stewart may have ultimate say in the creative and editorial decisions on the broadcast, but he isn’t pulling the show forward alone. Just the other day Stewart told longtime friend Denis Leary that he doesn’t expect to ever attain the level of collaboration that he has with the current staff:

“Here’s the thing I know I’ll never get again. […] I’ll never find a group of people like this again. I’ll never find a collaboration like this. I’ll never find writers and producers and all those people. And I know that. And I had to make peace with that.”

Of course, the most public aspect of the collaboration is in the writers’ room, where the narratives and jokes are crafted and refined. Comedy produced on a regular basis can be an intense daily grind with a deadline that has no flexibility, leaving little room for ego or concern about whose jokes make it to air. In fact, with the bench staffed with experienced comedy writers, Stewart isn’t necessarily present during the first morning meetings when the writers and producers spitball ideas. The New York Times recapped a panel in 2008 where Daily Show writers discussed their process:

“The staff members have their morning meeting, with the tidbits that have been pulled out by a rolling cast of writers, producers, graphics and researchers — many of whom have been working on ideas since the previous day, as news breaks. “We get specific about what angles we’ll be taking and we’ve all agreed to,” said Mr. Havlan, who has been working on the show since 1996. “We’re joking around from 9 to 10. Jokes from 9 to 10 frequently end up on the show.” Jon Stewart sometimes joins in at the end.

As the cliche goes, hire people that are smarter than you. When working on any project, surround yourself with people whose skills and abilities can enhance your work beyond what you are capable of alone.

Limitations Can Benefit Your Work

As imposing as it is to write and produce a literal daily show, the hard deadline and the resulting ephemeral nature of the show can actually be freeing. Jon Stewart has a background in stand-up comedy, and when talking with Jerry Seinfeld, Stewart explained that “In stand-up, new material is so much more precious. [With The Daily Show], like, I have to.” He has to produce something, he means. Being tied to the news cycle, by comparison, makes perfectionism almost impossible; the show must go on regardless of any writer’s block. As he explained to Rolling Stone, that constriction can be freeing:

“It’s easier for me to do this than when I used to do the regular talk show because […] there’s a news cycle to work off of. You don’t necessarily have to adhere to it, but you at least get to work off it, so it’s somewhat easier. […] It’s freeing because you don’t have to come in every day and go ‘What joke will I make about J-Lo’s derrière today?’”

Most of us don’t write jokes for a living, but it can be beneficial to approach your work without a sense of perfectionism. Waiting for a moment of inspiration will usually stifle your productivity more than anything. It depends on the nature of the work and the decisions at hand — I’m not talking about brain surgery — but acknowledging the ephemerality of the daily grind relieves the pressure that comes with the well-intentioned goal of getting your work just right.

Know When to Move On

Jon Stewart’s decision to leave The Daily Show while its still on top came as a surprise to many, but he had already talked about the necessity of leaving before any sense of ennui sets in. “I’m not interested in just going in and hitting the ruts that I’ve worn out,” he told Seinfeld last year. Of course, for many people, being able to leave your job is a luxury. But becoming too complacent with your work and simply clocking in every day is bad for your career.

You shouldn’t quit your job just because it’s not perfect, but remember that there’s a lot out there. When you feel like you might be able to find other work that you’re better suited for, it’s worth exploring the possibilities. And even if loyalty to your coworkers is holding you back, they will be fine. As Stewart told the Guardian: “The value of this show is so much deeper than my contribution”.

And now Jon is off to do whatever the heck he wants, leaving us for a time without a guiding voice in the venerable field of bullshit detection. Watching the show has been an education, personally — an education in comedy as a tool to make a point, and also how honest, thorough work can lay waste to the disingenuous noise of the world.