I want to leave my high-paying job, but health insurance is the one thing keeping me trapped
I’m 41, married, no kids, and I’m pretty close to the number where leaving my job should be possible. Not luxurious private island possible, but “reasonable life, paid off house, conservative withdrawal rate, part time work if needed” possible. Our invested assets are around $1.7M, house is paid off, yearly spending is usually $58-65k depending on travel and repairs. My wife works part time by choice and brings in about $18k a year, but her job doesn’t offer health insurance.
On paper, I should be excited. The problem is my job is slowly eating my brain. I’m in a high-stress tech management role and the money is very good, around $230k total comp most years. But the meetings, the constant reorganizations, the “urgent” weekend pings, the pretending every leadership pivot is inspiring instead of chaotic, it’s all wearing me down. I used to think I could just grind one more year, then one more year became three. I’m starting to realize I’m not staying because I love the cushion. I’m staying because I’m scared of health insurance.
My employer plan is excellent. Low deductible, great network, predictable costs. My wife has a chronic condition that is very manageable but requires regular medication and specialist visits. Nothing catastrophic right now, but enough that buying coverage on our own feels like staring into a fog machine. I’ve looked at ACA plans, but the premiums and out-of-pocket maxes make me hesitate, especially because our taxable income in early retirement would depend on how we structure withdrawals. I know subsidies exist, but I don’t want to build our entire plan around keeping MAGI perfectly optimized like it’s a second job.
Part of me thinks I should just keep working until 45 and make the portfolio so stupidly safe that healthcare costs don’t matter. Another part of me thinks that’s how people wake up at 52 still saying “just a few more years.” I don’t want to be dramatic, but the whole point of FIRE was supposed to be buying back time and health. It feels absurd that I can be financially independent in every category except “please don’t let medical billing destroy us.”
For those who left a high-paying job before Medicare age, how did you get comfortable with the health insurance risk? Did you just budget the full unsubsidized premium and worst-case out-of-pocket every year? Did you use ACA subsidies, part-time work, a spouse’s plan, or something else? I’m not looking for magic, just trying to figure out if this fear is rational planning or golden handcuffs wearing a hospital bracelet.