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Jay Leno, Here’s My ‘Now, What?’ Advice for You

An ex-public radio star offers pointers from her own experience


Jay,

I know it’s only been a few days, but how are you holding up?

It feels a little weird, doesn’t it? Not getting in the car (or motorcycle) and heading down the 101 or the 134 or the 110 or whatever to the office for a solid day’s work. At first it kind of seems like you’re just on a staycation. Of course this staycation could be a long one. And that’s what makes it different.

Career Transition Kindred Spirits

We are kindred spirits, Jay, BFFs in the arena of career transition.

I left my high-profile job in public radio a little over a year ago, when I walked away from being host of Marketplace Money, the weekly personal finance show. Like you, I didn’t really want to leave, but felt like I had to. And like you, when I left, I didn’t have anything else lined up.

(MORE: Jay Leno’s 6 Lessons for Leaving a Job You Love)

So since I’ve been in that space a few months longer than you and I’m now at work on a book about career choices, ambition and the pressure to have a linear trajectory in your work life, I thought I’d give you an idea of what it might be like for you now that you’re… in-between gigs.

A Sense of Freedom, At First

In these first few days and weeks, you will feel the freedom of the world laid out before you. (The last time you left your gig, you had another one to go to; sorry about how that turned out). This time, you have exactly one million options. You can be anything you want to be.

As the self-helpers would advise: Follow your passion! Do what you love!

Oh right — you already did that. Yeah, me, too. We had our dream jobs. We followed our passions. We did what we loved. So the self-helpers are really no help at all.

I see from the newspapers that you are not retiring. And why should you? You’re only 63!

(MORELaid Off After 50: 5 Do’s and a Don’t)

But I haven’t seen anywhere what you’re going to do next (I know you’re reportedly still under contract with NBC until September), except maybe some standup, which I would love to catch, having seen your act already twice in my lifetime.

No Plan, No Problem

You don’t seem to have a plan for your next career, and that’s totally cool. It’s great, in fact.

You wouldn’t believe how many people have done the same thing — leaving the work they’ve known for so long without a backup plan. We all know we’re supposed to have one, but trust me, lots of people don’t, including me.

My advice: Give yourself some time to chill, for sure. Go dip your toes in the fountain at Grand Park. Have a sno-cone out on Santa Monica pier.

Soon, though, you’ll find yourself feeling itchy to be… productive.

So maybe you’ll play with your cars for a while. Maybe you could earn a living that way somehow (though I‘m guessing that’s not your major concern — you did save at least 10 percent of your annual salary, right?).

Or you could start a motorcycle body shop. Oooh I like that! You could even get a TV show out of it! Oh, right — there already is one. Shoot.

(MORE: 7 Rules for Quitting Your Job Gracefully)

The Answer You’ll Need

You will need to come up with an answer to “What are you doing?” because it is the Incessant First Question of almost every dinner party and airline seat conversation (I suspect even in first-class).

People get very uncomfortable if you tell them you’re either in between gigs or figuring out what you want to do with your life or just hanging out having a good time for a while.

Many of them will give you sad looks of pity. And when you insist you left your amazing job of your own volition (I know your story is a bit more complex), they will give you looks of bewilderment and pity. So come up with an answer for that question before you do anything else.

Prepare yourself for the sudden realization that you’re no longer sure of who you are, now that you are no longer identified with what you did.

You are no longer “The Tonight Show’s Jay Leno.” You are just Jay Leno.

How to Get Comfortable Being Just You

Ok, you’re a little different than me this way, because your name will still go in the history books and your obituary will appear prominently in The New York Times one day. So you will always have a certain identity. But you won’t be going to that job that made you famous anymore. You’ll have to figure out how to be comfortable with just… being… Jay.

Finally, spend some time figuring out how you will deal with your own ambition and your Type A need to always be striving for the Next Big Thing.

After hosting The Tonight Show, you may have a tough time finding another gig to top it.

The Trouble With Peaking

Our career arcs are supposed to be a linear, upward trajectory, but after you’ve reached a peak, it’s hard to come to the realization that you don’t know where else to go or that anywhere else you do go will be, you know, downward. Former presidents deal with this, of course, and departing big-time corporate CEOs.

Maybe you could work for Habitat for Humanity or start your own charitable foundation. Just a few ideas I’m throwing out there for you, though really, it can’t and doesn’t get any better than hosting The Tonight Show, so pretty much you’re screwed. You’ve topped out. Sorry, buddy.

Call me anytime if you just want to sit down for a cup of coffee and a chat. I’ve been where you are now and I’m happy to provide more advice and perspective. If you’re cool with it, why don’t you go ahead and make the reservation at The Ivy? I’d like a table near the front.

Tess

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