If you’re like me and retire before Medicare and do not have a pension.
Besides finances, a massive part of retiring is health insurance.
My retirement goals:
Good health, freedom, access to a doctor and a million dollars.
“One million is not enough? How about one hundred BILLION” ?
– Dr Evil
THINK BIG … SCHEME BIGGER!
Health Insurance and inflation are always changing and, it is not something I do not 100% fully understand, yet. Honestly, I’m still learning as I go but, I have great advisors in my corner across the board that will help me stay on course:
Feel free to also check out my overall insurance blog by CLICKING HERE.
(Being under insured is something that I have never experienced).
An accident, medical emergency or prolonged illness can cost you far more than your health—it can wipe out everything you own as well. One serious accident or illness can destroy a lifetime of savings in a hurry without proper insurance.
I am glad that stressful time without health insurance is coming to an end!
Because if you know me, I stress the fuck out over this stuff!
I had a massive learning experience on my health insurance …
I went the entire first part of 2026 without health insurance in the USA.
Although, I still had travel insurance that would have covered me as I was in the Philippines, my American policy had actually been cancelled because of non-payment.
I’m unsure if I am Shrek or just a donkey for allowing this to happen!
The premiums changed for 2026, and since I wasn’t checking my physical mail or spam emails properly while traveling, I completely missed the notices.
It was a complete shock getting home from the Philippines on April 15th and finding out my policy was cancelled due to non payment. The following six weeks before my new policy starting on June 1st, I kept a pretty low profile.
I couldn’t afford to get into an accident and lowered my odds!
I tried not to think too much about possibly needing a doctor, although I really did need to refill my prescriptions.
Stressful lesson learned!
Set up auto-pay and review my health insurance policy every December.
There are also services now that will scan and email my physical mail while I travel, which honestly would have saved me a lot of this stress.
Ironically, I saved about $1,200 in premiums and never needed a hospital visit during that time. I also had travel insurance as a backup outside the USA.
Still… that’s not a money saving gamble anyone should be taking. 💰
Somehow I dodged the bullet, saved paying premiums, and never ended up needing a hospital. But let’s be honest—that was less “financial strategy” and more “accidental gambling on my life and retirement.”






