
Medicare Doesn't Stay Still
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VOLUME 2026 · MEDICAREEvery year, I hear some version of the same comment.
It usually sounds something like:
"I enrolled in Medicare a few years ago. I should be all set."
Frankly, it's what most of us would expect. We don't assume our homeowners insurance changes every year. We don't assume our driver's license changes every year. So why would Medicare?
After decades of making decisions about retirement accounts, pensions, Social Security, insurance, taxes, and investments, nobody is excited about adding another item to the list.
Unfortunately, Medicare doesn't reward the idea of "setting it and forgetting it."
In fact, it often does the opposite.
We just hosted a Medicare education webinar alongside Ryan Hickel, CPA, and independent Medicare specialist George Walters. We spent nearly an hour discussing enrollment rules, IRMAA surcharges, prescription drug plans, and the annual changes that catch retirees off guard. I recommend everyone age 63+ take a second to listen.
One theme kept resurfacing — most costly Medicare mistakes don't happen because people ignore their health. They happen because people assume nothing has changed.
One of the most surprising parts of our discussion wasn't about Medicare Advantage or Medigap.
Many people believe Medicare begins at age 65 — period. The reality is more nuanced: some people should enroll immediately. Others should wait because they're still covered by a qualified employer plan.
Some retirees unknowingly pay higher premiums because Medicare looks back two years when calculating IRMAA. Others qualify to have those premiums reduced after retirement — but only if they know the appeal process exists.
None of these decisions are especially difficult. But almost none of them are intuitive.
The same thing happens with prescription drug coverage. A Part D plan that worked beautifully last year may no longer be the best option this year.
- A medication can move to a different formulary.
- A preferred pharmacy can change.
- Premiums can increase.
- The drug itself may not change. The rules around it often do.
That's why spending twenty minutes reviewing coverage each fall can save hundreds — or sometimes thousands — of dollars over the coming year.
One topic generated more discussion than others — and rightfully so:
Medicare Advantage
If you've watched television lately, you've probably seen the commercials:
Those benefits are certainly worth understanding. But healthcare decisions deserve more than a thirty-second advertisement — and pitfalls can exist.
Every person's situation is different. Your health, your income, and where you travel. Whether you split time between home and another state, and the physicians you want access to.
There simply isn't a universal answer. What matters is making an informed decision — not a rushed one.
At Harbor Wealth, we've always believed our job isn't to pretend we're experts in everything. Our responsibility is to surround clients with specialists we trust. That's why we partner with independent Medicare specialists who help our clients evaluate their options objectively and answer questions we simply shouldn't pretend to know ourselves.
Perhaps the biggest takeaway from our webinar wasn't about Medicare at all.
It was about retirement.
The best financial decisions are rarely one-time decisions.
- That's true for investment portfolios.
- It's true for tax planning.
- It's true for estate plans.
- And it's certainly true for Medicare.
To watch the pre-recorded webinar, please go to our website, Theharborwealth.com → Events. The link is HERE.
Our team would be happy to connect you with one of the independent Medicare specialists we work alongside to review your current coverage or discuss upcoming enrollment.
Open Enrollment runs from October 15 through December 7 — many important decisions become significantly more difficult once that window closes.
If you — or someone you care about — is approaching Medicare or simply wants a second opinion, we'd be glad to make the introduction.
Helping clients make informed decisions — not rushed ones — is exactly why we hosted the webinar in the first place.






