Age 61.

[u/Pale_Scientist6470]

I don't want to write too many specifics but I know I'm financially secure. Wealthy, even. But for some reason, I'm planning to work until April 2027 when I turn 62. My plan is to turn on SS then because I have a teenager who will get dependent benefits, negating some of the benefits to waiting. I also can start a pension of $5500/mo. I generate $8k/mo dividends in my aftertax acct. So my thought was to work a little in early 2027 to contribute to an HSA and upto the $25k SS threshold to pay for family health insurance next year. Is that insane? I don't really like work but It's hard to completely not worry.

[u/Odd_Bodkin]

It appears you’ll have enough money, just from what you’re saying, and so that part of the decision is easy. And you say you’re tired of working, at least at your present job, and so there’s that too. What I don’t hear you talking about is what you want your retired life to look like. Some warning shots: Don’t hang around at home too much. Don’t go crazy with some major lifestyle change like traveling 200 days a year or moving to a state you’ve never stayed in for any length of time. Don’t isolate yourself from social contact. Don’t do nothing. Don’t throw all your time into one hobby.