Another interview with Jay Leno.
There are a lot of articles around about his departure from The Tonight Show and many of them seem to me to be missing an important point. Yeah, I think Jay would have liked to have stayed on indefinitely but I think he's okay with leaving. Somehow, this is getting translated into either, "He's upset about leaving" or "He thinks it's a great idea to leave now." Speaking for myself, I've never felt either way about a job I enjoyed and did for any significant length of time.
In this world, there are folks who think of a job as one place where you try to work until the day you're ready for retirement. And then there are those of us who go from job to job our whole lives, sometimes juggling several at a time, treating each one just as something they're doing for a while. I'm in the latter group: I've been a freelancer since 1969. I've never worked for one publisher or producer at a time, nor have I ever worked on anything that I felt I'd be doing for more than a few years…or in many cases, a few months. If I get hired to write a TV show or a comic book or a movie script or anything, it's just what I'm doing at the moment.
I have friends in the first category who can't understand how a person could live like that. Their lives seem to require the order and security that comes from an occupation where you can describe what you do in a simple sentence: "I do [job description] for [name of employer]" and they can expect that, apart from promotions, that sentence won't change in five or ten years. I have one acquaintance from high school who worked for the phone company from age 18 until he retired and to him, I'm just a guy who can't hold a job.
Leno is at heart a stand-up comic. It's about as "freelance" an occupation as exists in the world today. Even when you work the same club over and over, you go in, tell your jokes and leave. No office. No sense of being part of a staff. Jay got that from doing The Tonight Show but he never even did that exclusively, playing two or three stand-up appearances per week. He has a stand-up date the day after he does his last Tonight Show. I'm sure he'll miss the nightly gig but he's not losing his career or something he expected to last forever. And I suspect he doesn't need the money.