From the brilliant mind of Tanja at

Surprising as this may be to those who know my love of planning, I waited until fairly late to apply for coverage. California’s open enrollment goes six weeks longer than national open enrollment (until January 31 instead of December 15), and I mistakenly believed that the coverage was retroactive like COBRA. (Dumb, I know.) But we had such a long to do list otherwise, plus the stress of wrapping up work, and this was one thing that seemed like it could slide — so I let it slide.

I ended up applying over the holidays, thinking that was still well before the end of open enrollment, and would make a January 1 start date for our insurance easy. I learned too late, though, that even with the longer open enrollment period, the deadline for a January 1 start date was still December 15, just like on (D’oh!)

Healthcare is one of the biggest questions and scariest parts for most people looking to retire before age 65. This is a prime example of the absolute chaos that is the US healthcare system.

Early Retirement Health Insurance