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Jay Leno's 6 Lessons for Leaving a Job You Love

He'll get The Mark Twain Prize on PBS; how he handled his handoff

By Nancy Collamer

(On Sunday, Nov. 23, PBS stations will air Jay Leno: The Kennedy Center Mark Twain Prize, honoring the former Tonight Show host and featuring tributes from the likes of Jerry Seinfeld, Chelsea Handler, Garth Brooks, Wanda Sykes and Seth Meyers. Below is the Next Avenue article that appeared just before Leno turned his show over to Jimmy Fallon, with career lessons for all of us on how to manage a job handoff professionally.)

Tomorrow, Jay Leno, 63, will end his reign at The Tonight Show and hand over the job to Jimmy Fallon, 39. In a 60 Minutes interview with Leno, Steve Kroft described it as part of a shift beginning to affect millions of boomers being pushed aside to make way for a younger generation. “The inevitable changing of the guard that reflects a change in taste, sensibilities and values,” said Kroft.

Pushed Out While Still On Top

Inevitable? Absolutely. Every business should have a talent succession plan in place. But what makes this case troubling to some is that Leno, who loves the job he’s had for 22 years (aside from the brief Conan O’Brien era) and would prefer to stay, is being pushed out at the top of his game. He’s the late-night ratings leader and dominant in every demographic group, including younger viewers.

(MORE: What to Know Before You Get Fired or Laid Off)

While the particulars of Leno’s fame and fortune are exceptional — he’s reportedly receiving $15 million for exiting before his contract expires in September — his Tonight Show departure offers lessons for everyone approaching retirement age on how to leave a beloved job with grace and dignity.

Here are six key takeaways:

1. Don’t trash-talk your employer. While we can’t know what Leno has said about NBC behind closed doors, in public, he’s been all smiles. "It's been a wonderful job, but this is the right time to leave," Leno just told Associated Press television writer Lynn Elber.

This despite the fact that it’s the second time NBC has pushed him out and replaced him with younger talent (after the network replaced him with O’Brien in 2009, it asked him back less than a year later).

(MORE: An Ex-Public Radio Host Asks Herself, ‘Now What?’)

When pressed by Kroft to vent his outrage at NBC, Leno refused to take the bait. “I’m not bitter, not upset,” he said. “NBC has been more than fair. These are tough things and you know, you have to step back and go, ‘Look, you're getting a little old for this now.’ And that's where I am. So I’ll try something else.”

Leno’s attitude is an important reminder to never publicly bash your employer, no matter how well deserved. While doing so might make you feel better, it only serves to make everyone else around you uncomfortable.

2. Acknowledge your limitations. There’s something distinctly unsavory about watching a one-time star struggling to remain relevant after his or her prime has passed. (Paging Norma Desmond.) While Leno is clearly not yet at that point, he recognizes that the “relevancy clock” is ticking.

Leno told Kroft that when he saw Jimmy Fallon doing a dance number with Justin Timberlake, he thought, “I can’t do that.” He also conceded struggling to keep up with social media and pop culture, laughing when he couldn’t recall the name of Justin Bieber’s latest hit.

In Leno’s industry, the cool factor counts. In yours, a lack of technology skills or physical stamina might lurk as a ticking time bomb.

(MORE: 7 Rules for Quitting Your Job Gracefully)


3. Spread the light as you pass the torch. It’s easy to hold a grudge against the person replacing you, but Leno has gone out of his way to praise Fallon publicly at every turn. “I thought Jimmy has been especially gracious and polite,” Leno told Kroft. Leno even teamed up with Fallon to film a spoof making fun of all the late-night rumors.

Paving the way for your successor is not only a nice thing to do, it’s the right thing to do. As OgilvyOne’s Brian Fetherstonhaugh told Next Avenue: “Within an organization there’s a responsibility for passing on your knowledge — and sometimes your relationships — to make sure the place you move on from is in at least as good a shape as when you found it.”

To his credit, Fallon has been publicly kind to Leno, expressing his admiration.

Appearing on Leno’s show Monday night, Fallon read a “thank you note” to Leno which said: "For carrying on the proud tradition of The Tonight Show host with such humor and class, and for being nothing but gracious and generous to me over the past years. I will do my best to make you proud, every night. Thank you." (Fallon then made a huge faux pas, however, asking the band: “What are you guys up to in two weeks?” When the show moves to New York, its 164 staffers will effectively lose their jobs, though they’ve been encouraged to apply for new ones.)

4. Keep it in perspective. If you’re shown the door before you think it’s your time, try to understand your employer’s situation. That’s especially true if you’re a highly compensated employed who, on balance, has been treated well.

“You think I should be angry or bitter?” Leno asked Kroft when pressed about his true emotions. “I mean what you’re saying applies if you’re making $27,000 as a Wal-Mart manager and you get fired. But you know when you make the type of money you make in show business, just shut up and don’t complain.”

5. Prepare for the possibility that you might “get screwed.” Leno told Kroft: “I always tell new people in show biz that show biz pays you a lot of money because eventually at some point you’re going to get screwed.” Even if you’re not in show business, Leno’s advice to save and plan for the future is wise. This way, you’ll be ready financially if your exit happens earlier than you’d hoped.

6. Start planning your post-retirement gig earlier rather than later. The day after Leno leaves Tonight, he has a standup show booked in Sarasota, Fla. Last year, on top of his late-night duties, he performed live more than 100 times.

It’s never too early to start planning for your next act. So begin cultivating your hobbies, testing out your interests and building a side gig. For tips on how to do it, read “Starting a Side Gig After 50: A How-To Guide.

As Featherstonhaugh told Next Avenue: “There will be a chapter three. Whether it will be rewarding and nourishing or a bummer is up to you.”

Photograph of Nancy Collamer
Nancy Collamer, M.S., is a semi-retirement coach, speaker and author of Second-Act Careers: 50+ Ways to Profit From Your Passions During Semi-Retirement. You can now download her free workbook called 25 Ways to Help You Identify Your Ideal Second Act on her website at (and you'll also receive her free bi-monthly newsletter). Read More
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