Too many factors in play to know for sure. I’m 53. By 56 I should have my mortgage paid off, all my debt gone, and have enough in my 401k to be able to say “enough” (aka F.U.) at any point. But I won’t be eligible for retirement health insurance benefits through work until 62. And I’m nearly at the top of the food chain at work, so as long as my staffing gets normalized and I am not as overextended as I have been this past year, will I want to leave early? Maybe reduce at age 60 to working 8 months a year, March-June, Sept-Dec allowing for summer sailing and winter snowbirding until 62?