My situation:

37 years old
Same corporate (high net worth individual) for 11 years
Owner is 75

I now have another opportunity for a high net worth individual, $20k more per year, better quality of life (more time off). Boss is ten years younger.

I’m concerned that my boss will die and I’ll be jobless, which is why I am considering the job described above.

Do I move on to this job? I’d say the job I’m offered as good, if not a bit better than where I’m at.

But should fear of the boss dying be enough to make a job move?

I'd make the move.

Lots of variables you haven’t mentioned, but I would just have a discussion with you current principal about his plans for the future of the plane. Just be honest with him(her).

I turned down a dream corp job once when I was on furlough, because the owner was 70 something. I mean it was truly “the” dream job, but everyone speculated the job couldn’t last more than a couple more years. The owner lived well past 90 and continued to travel til almost his last days. This was in early ‘80s, when longevity wasn’t expected like today. The estate continued to use the plane for a couple years after he died, and I heard the crew got an awesome severance (retirement), that had been specified in the owners will.

Yeah, the safe odds say make the move. Usually better to do that on your terms rather than as dictated by circumstances.

PMEP100's anecdote is not the typical case.

That’s my thought exactly... make a move on my terms. I’m simply concerned that when the time comes that I NEED a new job, the jobs that are available won’t be nearly as good as the one that I’ve been offered.

What is the current owner's health like? Lifestyle? Is it just age you're worried about or does he drink a white russian at six AM in the morning before takeoff? stack up the pros and cons on a piece of paper before jumping. Something about grass being green... on the other side of the runway...