Career Lessons From Conan O'Brien

A new documentary about the late-night TV star shows what he did when finding himself jobless.


It was hardly a typical career disruption last year when Conan O'Brien left the Tonight Show, in the big, tiresome brouhaha over NBC's late-night lineup. O'Brien complained relentlessly about the shabby treatment he felt he got from the honchos at NBC, giving voice to millions of others who felt the same way toward their own bosses (or former bosses). But he also got a $32 million settlement from NBC—the kind of rich severance package most displaced workers can only dream about.

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O'Brien suddenly had something in common with other out-of-work people, however: He had to figure out what to do next. Now, a lively new documentary, Conan O'Brien Can't Stop, reveals the TV showman's anxiety and manic creativity as he worked with his staff after the NBC flameout to devise his next act. O'Brien ultimately ended up with a new late-night show on TBS, but between his NBC and TBS gigs, he gave live stage performances in 32 cities, dubbed the "Legally Prohibited From Being Funny on Television Tour." The documentary, directed by O'Brien's college pal Rodman Flender, shows how O'Brien and his team came up with the tour idea, developed the material, and tromped grudgingly from city to city.

It's a funny and unsparing portrait of O'Brien that mixes footage from his comedy shows with many unscripted, offstage moments. The film is highly entertaining—even more enjoyable than O'Brien's current show, on most nights—because the wired comic can be as hilarious off the stage as he is on it. He also has a biting, sarcastic streak—which colleagues refer to as "Mean Conan"—that's unflattering and assures that the film is not just a promotional vehicle. Viewers will also see some of the clever ways the driven entertainer kept his career going after losing his dream job. Ordinary working stiffs may not have the name recognition or other advantages O'Brien did, but there are still some takeaways from the film that regular folks can apply when they hit their own career obstacles. Here are some of the things Conan O'Brien did when he found himself jobless:

Blame himself. But not for long. One of O'Brien's on-stage soliloquies during his tour covered the eight stages of grieving he went through, after losing his job on the Tonight Show. Stage 1: Denial. Stage 2: Blaming himself. "Screw that stage!" O'Brien told his audiences. "I did nothing!"

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Vent. Stage 3 of his eight stages of grieving: Blame everybody else. "That's a good stage," O'Brien joked. Throughout the film, both onstage and off, O'Brien describes the anger he felt at being dumped by NBC. "I don't think I was entitled to do the Tonight Show," he tells the camera at one point, "but sometimes I'm so mad I can't even breathe. It's like a gallstone that has to work its way through my urethra. Eventually it will drop into the toilet and I'll be done with those [bastards]."

Improvise. Obviously O'Brien did that on stage, while interacting with audiences, but it's also an apt metaphor for what he did with his career. O'Brien and his team hatched the idea for the comedy tour in a series of brainstorming sessions, and fleshed it out as it took on a life of its own. "I'm 46, and what do I do now?" O'Brien wonders aloud early in the film. "All I know is I really like being in front of an audience." So given the chance, he decided to spend some time doing what he really liked.

Commit to something. The O'Brien team started booking theaters and promoting the tour before they had figured out what the show would be about. "Nothing motivates you to figure out what your show is like selling a bunch of tickets," O'Brien explains. "We're making it up. First, you gotta sell tickets. Then you come up with a show."

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Try something new. O'Brien didn't have a Twitter account and described himself as a technology Luddite when he left NBC. With help from a couple staffers—and some devoted fans—O'Brien started Tweeting in February 2010, promptly becoming one of the most-followed Tweeters on the Web (@TeamCoco). That following revealed the power of social media and helped O'Brien spread the word about his revival. Most of his shows sold out quickly, with Twitter being a major factor.

Laugh at himself. O'Brien is much more likable when he's poking fun at himself than when he's complaining about being mistreated by a firm that paid him $32 million to go away. When he and his staff arrive in Eugene, Ore., for one of the first shows of their tour, they disembark from their private plane onto a tarmac that's almost completely lifeless. "Get this crowd back!" O'Brien shouts, as staffers giggle. Later, in a car en route to his hotel, O'Brien, still worried about turnout, says, "I think, for security, we should change our hotel at the last second. [Pause.] I learned that from Saddam Hussein."

Ceaselessly self-promote. A recurring theme throughout the film is O'Brien's willingness to meet with anybody and do almost anything if it will help promote his show. He glad-hands with an endless stream of fans and promoters, even though he complains about exhaustion and worries that he'll lose his voice and be unable to perform. "Nobody's thinking about burning me out," he grouses at one point. "When I burn out and everybody who's working for me doesn't have a job, they're going to think about it." Then he heads off to another meet-and-greet that somebody has told him is essential.

Relax. If only for a moment. When the tour is nearly over and O'Brien seems spent, he says, "This is the most exciting thing I've done in show business, but you can see the sickness in it, too. I love this, but I can also see that it needs to stop pretty soon." The frenetic showman yearns for a brief interlude of boring domesticity: "I need to go home and drive my kids to school," he deadpans. "Or have my agent drive my kids to school."

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O'Brien didn't need to go on tour at all, and he would have gotten his next job, with TBS, even if he had stayed at home and said nary a word until he returned to TV. But he felt the same restless need as many others to do something productive and therapeutic, to keep working, basically, even if it felt like a diminished platform. O'Brien peddles laughs—not career advice—but Conan O'Brien Can't Stop provides generous helpings of both.

Twitter: @rickjnewman