The six decisions that make Medicare at 65 hard
Each guide states the rule with its number, shows what it costs when it goes wrong, and links to the calculator that does the math for your situation.
Still working at 65
The 20-employee rule, who pays first, and the 8-month window that starts when you stop.
Read →Enrollment windows and penalties
Seven months, eight months, and the 10%-a-year penalty that never expires.
Read →The income surcharge (IRMAA)
Two-year lookback, six tiers, the appeal form, and Roth-conversion timing.
Read →Retiring before 65
COBRA, the marketplace after the 2026 subsidy change, and bridging 36 months of coverage.
Read →Medigap vs. Medicare Advantage
How to think about the choice, and why the first six months matter more than the plan.
Read →Medicare and your HSA
Why Part A backdates six months, and the exact month to stop contributing.
Read →Not sure which one is yours?
A 30-minute conversation usually settles it. No cost, no plan sales, statewide by phone or video.
Talk it through before you decide
Bring your birth date, your work situation, and last year’s tax return. Leave knowing your enrollment window, what Medicare will cost you, and whether the income surcharge applies.
- No-cost, no-obligation consultation
- Statewide by phone or video
- Education first — no plans sold here
Request your no-cost consultation
Tell us how to reach you — we follow up within one business day.