I know - and the best news is that I am completely confident in the plan and not worried at all. The timing was just so freakin' predictable.
DH sold a bunch of his stock options last week and managed to do it at almost their all time high, so there's that...
Great thread. I am in a similar spot. We've been FI for several years, but that option vesting carrot is strong. I've really been OMY'ing it since 2016. I tried to quit last year and my last day would have been within a couple of days of the market peak last September, so by December I was kind of glad I hadn't. My boss's boss pushed me to stay, giving me a completely new role which is very low stress (I went from managing 65 software developers scattered across the globe - US, India, China, etc. to managing 0 and doing a bunch of low priority side projects.) I want to pull the trigger soon since options vested last month and financially we're fine. But at 51 I have similar concerns about healthcare for the next 14 years. One thing I've been thinking about is NFW am I working until 65 so I'll have to deal with the healthcare nightmare at some point. 18 months of COBRA gets us through the next election.
DW has been retired for a few years for a variety of reasons, so she's kind of waiting for me. But, last year it was easier to quit, I hated my job, I had a new boss who I didn't like, the hours were ridiculous since I was basically on call 24x7. Now I have none of that. My job is just boring, but damn they pay me a lot for the amount of work I'm doing. So I've been dithering a lot.
And as Much Fishing to Do points out there is the possibility of needing to focus on parental care. 3 of our parents are in their late 70s and while healthy now, I can certainly see a few years down the road where we'll need to take care of them and then suddenly we'll be old and need to be taken care of ourselves.