Look, I'm not going to lie to you. Nobody ever just woke up one morning and thought, "Of all the things possible in the vastness that is life, what I'd really like to do is play smooth jazz 250 nights a year." It just doesn't work that way.
It's not something you can plan for—it's all circumstance, I swear: You want to play music for a living. You bust your ass paying your dues in tiny clubs with six people in the audience. You think about all the talented jazz musicians out there who can't make ends meet and you start to worry. The next thing you know, your agent has you filling out forms to legally change your name from Mel Jablonsky to Michael Langello, and it's seeming like a good idea. Then suddenly you're 40 years old and you open up your dresser drawer to find nothing but linen pants.
There are a few stumbles -- for instance, never in the entire history of school band programs has the alto sax ever been "the only instrument left." (More typically, school bands have, like, at least a dozen alto sax players and no one willing to even try the bassoon.) And like any other musical endeavor, smooth jazz isn't actually all that lucrative, except for a tiny handful of inexplicable superstars. "$6,000 to $14,000 a night"? Dude, where do I sign?
On the other hand -- "'I'd like you to meet my very good friend, Chuck Mangione'"? Priceless.