Free PDF Guide
The Understanding Medicare Guide
Medicare is a maze of windows, penalties, and income tests — and the defaults are rarely in your favor. The whole system, explained once, clearly.
What’s inside
The parts, in plain English
A, B, C, D — what each one covers, what each one costs, and how they fit together.
Enrollment windows and lifetime penalties
The seven-month initial window, special periods, and the late-enrollment penalties that never go away.
Advantage vs. Medigap
The real trade — networks and out-of-pocket caps vs. premiums and freedom — and why the first choice is hard to reverse.
IRMAA: your premium is income-tested
The surcharge cliffs, the two-year lookback, and the appeal that works after retirement drops your income.
Working past 65
Employer coverage coordination and the HSA contribution cutoff when you delay enrollment for a workplace plan.
The annual review
Plans change under you every year — the October-to-December window and what to actually compare.
Written by Jim Crider, CFP®, founder of Intentional Living FP — a fee-only fiduciary wealth management firm in New Braunfels, Texas.
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This guide is educational only and is not specific financial, tax, or legal advice. Tax figures reflect 2026 rules and are subject to change. Fee-only fiduciary · No commissions · Always on your side of the table.