You don't want to regret not knowing your kids in 10 years when you retire (like you said). You are in the trap of making so much money that you can't get a lateral job without starting over down a few rungs on the ladder. My sister is in the same spot where she feels she has to keep working at the job as anything else would be a huge step back. But you are at the advantage that you have a ton saved and don't spend a lot, so if you know this and really don't need more money, why not just retire? Or even ask for a sabbatical, take a lower position in the company, switch to a no stress local job where you can leave work at the office, or take a part time job. If you're making $500k now and I assume are in a HCOL area then I'm sure you are very good at your job in a competitive industry, and you could probably (if you are looking to move) go somewhere in a LCOL area and be a big shot that can make your own hours/rules, etc. All signs point to retire, but I imagine a person at your level enjoys the type of work you do at some capacity and it's tough to go from overloaded to absolutely nothing, so will you really miss at least part of the office if you retired? Think about if you would get bored, miss the mission, etc. That may help lead you into the right kind of "retirement job" if you think you will miss work. I'm in the opposite place where I moved to a LCOL area from a HCOL so I could focus more on work/life balance, raise the kids in a right area, etc. but I find myself frustrated w/lack opportunities for promotion, so I've pretty much killed my career for promotion, however I have to constantly remind myself that being promoted would add more stress and more hours without a whole lot more money. If you find the right balance that helps your family life without being bored then I imagine you would be happy.