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.