06/01/2026
Medicare planning is one of those retirement decisions that sounds simple…
Until you actually get close to it.
Then come the questions:
-Should I enroll at 65 if I’m still working?
-Can I keep contributing to my HSA?
-Should I choose Medicare Advantage or a Medigap plan?
-How will my prescriptions be covered?
-Could my income cause higher Medicare premiums?
-What happens if I retire before age 65?
And suddenly, Medicare feels less like a benefit and more like a part-time job with acronyms.
But these decisions matter.
A poorly timed Medicare decision can lead to penalties, higher premiums, coverage gaps, or surprise costs that may have been avoided with better planning.
It also overlaps with tax planning.
Roth conversions, capital gains, IRA withdrawals, pensions, Social Security, and other income events can potentially increase Medicare premiums through IRMAA.
That does not mean you should avoid good planning.
It means you should understand the ripple effects before making big retirement decisions.
The goal is not to become a Medicare expert.
The goal is to coordinate Medicare with your retirement income, tax strategy, healthcare needs, and overall plan.
Because retirement planning is not just about investments.
It is about making sure all the pieces work together.
If you are within five years of retirement, Medicare should be part of the conversation before you are staring at enrollment forms, wondering why retirement came with homework.