It's an interesting question. I'm wondering if I'll regret hanging on a bit longer. I was very close to jumping 10 years ago, and again about 4 years ago, but each downturn knocked my nest egg back so I'm glad I didn't. Now I'm back to having enough for a 3% SWR including a small pension and social security, or 4% with just my 401K, IRA, and other funds. If I've set my budget correctly, which I think I have since it includes house and car maintenance, vacations, and a set aside for capital expenses. I could also downsize my house if it looks like I can't make it.
The thing is, everybody tells me I've got the perfect job, and I tend to agree. I'm working 1/2 time, the pay is decent, benefits, and I telecommute with flexible hours. I like the work ok, and it's pretty slow. I do software support for what's now a pretty stable product, and they just want someone around in case something goes bad, and in the meantime I keep as busy as I want to be (or not) with minor enhancements. Even when the pressure is on, it rolls off my back. I figure if things go bad, I can bail, but why walk away when I've got it good. I'm 47, so I feel like I've still got lots of time to spend any extra I put away.
I had hoped a buyout might come, but they just offered one and you have to be 55, so I probably won't see one in my work life. I thought I might get a layoff package, but the last two missed me. Who knows if there'll be another one. It wouldn't bother me to get a severance package, rather than just giving 2 weeks notice.
Once I leave am I going to wonder why I kept on, or does it seem reasonable to stick around in a good situation and kept building the nest egg?
If I left and felt it was a mistake and needed to come back, I doubt I'd get rehired, and there's only 3-5 companies at which I'd be able to use my specialty to get hired, and I probably wouldn't have as good of a setup, like working part-time. And in 5 years, I'd probably be a dinosaur.