I'm 63 and I keep going back and forth on the timing. The math says I'm ready — portfolio's where it needs to be, expenses are under control. But there's this psychological weight I didn't expect. The paycheck stops. The structure goes away.
I've been reading everything I can find on the transition and most of it is either too abstract or written by people who retired at 55 with a windfall.
What's the thing that's actually keeping you up at night? For me right now it's healthcare — the 2-year gap before Medicare if I leave at 63 feels like a real cliff. Would love to hear what others are wrestling with.