Long time lurker .... first time writer ever here or elsewhere. Have to decide whether to early retire with 60 weeks pay and benefits in the next 36 hours. Job is very stressful and little satisfaction for past few years. Know I've worked hard and am very fortunate and blessed to have saved early and regularly. Think I am set but insanely nervous nonetheless. Married 58 year old and been with megacorp for 25+ years. Have about $3.5M in deferred comp (a third of which gets paid at termination), $2.6M in 401k/IRA, and $750K in brokerage account. Expenses (yes, I know too high) run about $270K annually (includes $350k remaining mortgage and health costs but not taxes). Another $700 K coming over next two years from restricted stock. Have a freshman in high school who will go to college but $220K in a 529. Deferred pension of $29K a year starting in 2025. Will wait for Social Security until full age or 70. Firecalc and Fidelity planner lead me to believe okay but still worried about downturn in market, health costs, kid in high school and his college down the road. How does one ever feel comfortable jumping out? What am I missing?