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Medical Insurance: The Ultimate Full-Time Hobby

  • Writer: Sue Leonard
    Sue Leonard
  • May 25
  • 3 min read

It’s a good thing retirees don’t work full-time—because navigating medical insurance is a job in itself. I’m convinced the system is designed to test our stamina, sanity, and ability to survive 55 minutes of hold music without hurling the phone.


frustrated woman on phone Created by AI 5/25/25
Created by AI 5/25/25

Let’s start with January. The New Year brings new beginnings and, naturally, deductibles that reset themselves like clocks after a power outage. So imagine my surprise when my eye drops, normally a painful $200 for a tiny bottle, suddenly cost $450. So I’ll keep my vision, but need stronger blood pressure meds.


But here’s the kicker: my prescription plan doesn’t have a deductible. So we called the helpline—aka the Insurance Olympics. That day’s featured event? The Agent Handoff Relay. We spoke to five different people, spent 55 minutes listening to the same 10-second ditty on repeat, and got the same wrong answer: “You haven’t met your $4,000 deductible.”


“Yes,” we said, “on the medical plan. But not the prescription one.”


At least we understood each other this time. In the past, with overseas help lines, calls felt like playing a game of Taboo, where you try to get someone to say "snow" without saying white, cold, or winter.


So, before the next call we cracked open the insurance booklet, thicker than the Oxford Dictionary, but harder to read, and there it was: no prescription deductible.


Round two: same song, different agents. But this time, Hubby, now in full “Insurance Warrior” mode, demanded a three-way call with both companies. Genius. That’s when we found the culprit: my eye drops had  mysteriously been bumped from Tier 2 to Tier 3. Translation: same drops, fancier price tag. Strange how errors always work in the insurance company’s favor.


Pro tip from Consumer Reports: front-line reps can’t transfer you to a supervisor unless you ask. (1) Apparently, yelling “GET ME SOMEONE WHO KNOWS WHAT THEY’RE DOING!” is frowned upon. Better to save the rants for the dinner table, where friends nod and swap their own insurance horror stories.


And we’re not alone a Reddit post said:

“I got quoted $6,000 for an MRI. My insurance said the claim was denied.Two hours and four phone calls later, I found out it was covered 100%. I’m relieved… and furious.”

doctor stamping a document denied. Created by AI 5/25/25
Created by AI 5/25/25

One commenter said the confusion is by design. (2) Most people won’t fight back. Not us. We’ve got unlimited minutes and iron-clad stubbornness.


Now, about our mail-order pharmacy. It sends 90-day supplies… every 70 days. So we end up with a growing stash of unused pills—enough to open our own Walgreens. Being good citizens, we don’t trash or flush them. Instead, we make cheerful little field trips to the police station’s drug take-back box. Nothing says "fun outing" like handing Lipitor to a uniformed officer.


box of perscription meds Created by AI 5/25/25
Created by AI 5/25/25

I've accepted that modern life includes long hold times, confusing policies, and mysterious drug tier shifts. So now I treat each insurance call like a camping trip: snacks, tea, phone game, and whatever it takes to mute that awful hold music without spiking my blood pressure.


When it comes to insurance UK and Canada have it made. Listen to what one smug Brit shared in the Reddit insurance posts.


“I saw a doctor for back pain, got referred for an MRI, paid 25 euros, and was reimbursed 17. A week later, scan done. No copay. My insurance is 48 euros a month. I laugh at you Americans.”


But hey, I’ve heard it takes months to see a doctor there too. We’re not much better. In November I tried to get a hearing aid appointment at my local big-box store.  First appointment? March. Then it was canceled the morning of and rescheduled to May. That’s six months. Good thing I’m not completely deaf. The delays are not surprising, since the average age in our city is 64 and the most common word is “What?”


Anyway, I guess I shouldn’t complain. Two hours on the phone saved us $250.  That’s a salary of $125 an hour – not bad for a retiree.


Epilogue: Keeping Perspective

Yes, the system is maddening. But I’m not as angry as the man who shot the UnitedHealthcare CEO in 2024—a horrifying act that reflected a deep well of real frustration and grief. We’ve been lucky. We haven’t lost anyone due to denied care. But many have, and that’s no joke.


So I’ll keep laughing. It keeps me sane. But deep down, I’m hoping someday we’ll have a system that doesn’t require a law degree, a Bluetooth headset, and a bottle of Tylenol just to get some eye drops.


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