I'm going to take a contrarian view from all the people clutching their corporate health insurance for dear life.
You need to retire as soon as you hit that vest. Do not look back. Do not go for "just one more year". Circle the date on your calendar, make a plan, and then spend the rest of the year drafting your resignation letter. You're polishing cannonballs over there. The game you're hunting has stood up on its hind legs, walked right up to your shotgun barrel, and started licking the front sight. Click off the safety and pull the trigger. Seriously.
Plugging my particulars into ehealthinsurance.com, it looks like I could get a plan hat covers everything after a 10k deductible for about $500 a month. That's not chicken feed, but its doable, especially as I believe health insurance premiums are deductible for the self employed. It will be interesting to see how much that changes in a year.
I think you're risking your health as it is, and it's a testament to your endurance that you've lasted as long as you have. You don't need to find out that you're living on borrowed time. Once you retire you'll shed all the stress and you probably won't even need the health insurance... except for all the cosmic-ray exposure you're getting up there. Can you shave some off the ehealthinsurance quote with even higher deductibles and a HSA? How accident-prone are your kids?
I can't remember whether your spouse's employment has never come up before, but am I the only one here who appreciates the irony of advising a guy whose better half is a freelance career counselor? Can you get a free hour's consultation from her before deciding whether her advice is worth her fee? Please don't tell her I suggested that.
You've done everything you can do within the last five years to make your life better, short of leaving the workplace. When I think of our first lunch in 2007, we've both come a long way. I'm pretty sure you know what Bob Clyatt and BUM would tell you now. You've improved your geography, your employment, your bosses... and that's just not going to get any better. You've already spent a couple of years proving that you've done all you can do to "fix" the workplace.
What's your downside here? Living off squirrel pot pie and a backyard veggie garden and homebrew? (No need to answer that.) I think that once you're free of the office and the commute and the business trips, you'll get caught up on your sleep. You'll be outdoors more of the time and your fitness will bounce back pretty quickly. You'll be spending time with family so your morale will improve. (Although I could point out that morale could hardly get any lower.) Your head will be full of ideas. You'll monetize your blog. You'll offload your spouse's housekeeping/clerical duties so that she can grow her business. You'll never pay retail prices for meat ever again, and you might even be selling your excess. You'll become a nationally-ranked homebrew judge. (No need to answer that either). You'll find more value-investing ideas than Ted Weschler & Warren Buffett combined. (E-mail me when you're seeking shareholders.) You'll start any kind of side business (because that's who you are) on your own terms and your own hours, and within five years you'll be earning $40K/year plus capital gains, and your spending will be down to a 3% SWR.
The only thing you have to gain from work is a bonus with a small pension. You have way more to lose than just some health insurance premiums. If all else fails then you can take a year off and see how you feel about going back to your career field. Tell 'em you worked at a dog daycare center for a year to learn how it feels to be respected as an employee. I know a guy who's always looking for good help.
Think of how much fun it'll be to see your kids grow up into teenagers, and then to spend all of those years afterward persuading them to move out of the house. When it's over, you'll be happier that you were suffering at their hands instead of from your boss & co-workers.
Yeah, I know. Lifestyle advice from a guy with a federal COLA'd pension whose health insurance only costs $45/month. But I've seen what the corporate cubicle culture does to guys in your situation. I think you'd be much better off retired and worrying about where to get $500/month for your health insurance than you would be on medical leave from the office while you're trying to get out of the ICU.
Once you've had a couple months to decompress and relax, I think you'll be amazed by the
stupdity opportunities all around you. The bar is not that high. You'll have the motivation & time to dig into the financial research that you certainly have the aptitude and stamina to do. You'll find all sorts of ways to cut expenses around your house. Your contacts will be pestering you for consulting, even if they're 2-3 time zones away.
I can't think of a single thing that you could do to make you more ready than you are right now. Take the leap.
