Certainly depends on what you are looking for in your stage of life and what org you work in. I've generally had a good nearly 20 year run (came from an acquisition though). Left for a few years to try the startup thing, then a different company, in both cases aside from income I felt like I was going backwards in my career. Returned to O, into the same org which I had left, I continue to be compensated much higher than average, I get respect, I'm not managed, just pointed in a direction, work on reasonably cool stuff. I've been asked once to step into management and said no thanks, but continue to lead and mentor others as I go along. I still have a long 18 years before normal retirement and am not a person that can just "turn a crank", and I don't find it hard to retool and learn and my management supports this. Not knowing the future, but if I can make it to retirement at O that would be good by me. To be fully satisfied though, I do not rely on my job to make me happy all the time, just glad it is interesting enough. If I was to win the lotto though, or come across a dream job (something I have zero experience or training in, but would still provide the same income and benefits) I wouldn't think twice about leaving.