I’m two weeks away from a big birthday that I had been looking forward to for a single reason: Medicare.
While my advancing age — 65 — is nothing I feel like celebrating, the promise of health care insurance relief, at the metaphorical 18-mile mark of life’s marathon, had been motivation to keep putting one foot in front of the other.
I helped care for my mom in her final years. Managing her finances, I couldn’t help but notice that she didn’t pay a dime for medical care. Through surgeries, hospitalizations and prescriptions, I don’t think I ever saw a bill — only “explanations of benefits.” It turned out Medicare alone wasn’t covering her expenses. Her former job, as a secretary to the principal at my high school, came with supplemental medical and long-term care insurance.
To the untrained eye, though, it seemed that the flimsy red, white and blue paper card she regularly fished out of her giant purse unlocked a superpower.
Older and wiser now, I’ve come to learn: It’s not that simple.
In the months leading up to my April birthday, I started getting mailings from Medicare “navigators” — certified helpers who sent dense, multipage missives with charts and graphs that went straight into the recycling bin. Friends who had already been through it referenced the experience of signing up like shaken airline passengers deplaning after a turbulent flight. They were full of warnings about deadlines and penalties and choosing the right additional coverage to “fill the gaps.”
What “gaps”? I didn’t like the sound of that.
Following in the footsteps of two elders, I called Sandy Anderson of Medicare Northeast, a licensed independent consultant whose husband once co-owned the storied Burlington music venue Hunt’s. Foolishly, I agreed to meet in her South Burlington office on a Tuesday afternoon, the day Seven Days goes to press and I’m normally glued to my computer. She started the lesson by explaining that Medicare is woefully out of date: The original plan does not accurately reflect longer lifespans, higher medical costs and pharmaceutical inventions. We’d be going over its four parts — A, B, C, D — as well as a dizzying number of “supplemental” insurance options.
Anderson gave me a handout and was 30 minutes into explaining the details of the first column, “A,” aka “hospitalization,” when I started to sweat. I could see she had three more columns to cover and started to worry about being away from the office for too long. And, of course, we were talking about hypothetical pints of blood, “durable goods,” home care and hospice for me — not my mom.
“How long is this going to take?” I asked somewhat rudely. “I’m sorry, I thought it would be, like, an hour.”
In my second session with Sandy, at $125 an hour, she got into the real nitty-gritty. While Medicare Part A is free, Part B — which covers physician expenses — has a variable price tag based on your tax return two years prior. Part D, also on a sliding scale, covers prescription drugs, but there’s an annual deductible.
Part C is the additional insurance you buy to cover everything A, B and D don’t. First you have to choose between two routes — Medicare Advantage or Medigap — each with its own restrictions, pros and cons. The Medigap plans, from A to N, are yet another bowl of alphabet soup, offered by private insurance carriers at different prices.
By the end, my head was spinning. Bottom line: All the Medicare parts I need add up to more than the cost of my current monthly premium! So, it looks like I’m going to stay where I am for now: in a broken health care system. Frankly, not the birthday present I had hoped for, nor an enticement to quit working. But it’s certainly a relevant topic for this week’s Money & Retirement Issue — and proof the two subjects are linked.
Meanwhile, Charlotte author Stephen Kiernan, one month my senior, has been celebrating. As a self-employed writer with kids, he has shelled out so much for health insurance over the years that turning 65 brought measurable financial relief. He marked his birthday last month with a “Medicare party.” The way Kiernan, and Anderson, figured it, he just got a $16,000 raise.
This article appears in The Money & Retirement Issue 2025.


