Your Medicare roadmap. A few questions, one clear plan, zero sales calls.

Tap any dotted word for plain English.

When were you born?

Yes, we're opening by asking your age. Forgive us. Every Medicare deadline hangs off your 65th birthday, so this one date does most of the work.

At 65, whose health insurance will be covering you?

Whether you work doesn't matter here; what matters is whose plan covers you. COBRA and retiree plans count as "nobody's."

When do you plan to retire?

A rough guess is fine. Every date in your plan adjusts if this moves.

Are you putting money into an HSA?

A Health Savings Account: the tax-free one that pairs with a high-deductible work plan.

    Planning as a couple? You each get your own timeline, so run it once per person.

    Your personal timeline

    All calculated from your birthday. Orange means "soon." Tap any step for the details.

    The one big decision

    Everyone on Medicare picks one of two roads, and there's no sign warning you that one of them is hard to reverse. Consider this the sign.

    Path A: Original Medicare + Medigap + Part D

    Any doctor and predictable bills, for a steeper monthly price
    • See any doctor or hospital in the U.S. that takes Medicare. No networks, no referrals
    • Medigap fills most out-of-pocket gaps; bills are small and predictable
    • Coverage travels with you anywhere in the country
    • Higher monthly cost: Part B + Medigap premium + Part D drug plan (often $300–450/mo total)
    • No dental, vision, or hearing; you'd buy those separately

    Path B: Medicare Advantage (Part C)

    Lower monthly cost, more asking permission
    • Low or $0 extra premium (you still pay Part B)
    • Usually bundles drug coverage, plus extras like dental and vision
    • One plan, one card. Simpler on paper
    • Networks: your doctors and hospitals must be in-plan; plans can change networks yearly
    • Prior authorization: the plan can require approval before covering care
    • Out-of-pocket costs can reach $9,000+ in a bad health year

    What Medicare costs in 2026

    The standard amounts. Higher earners pay more; details in the note below.

    ItemWhat it is2026 cost
    Part A (hospital)Inpatient care. Free if you (or spouse) worked 10+ years$0/mo for most
    Part A deductiblePer hospital stay benefit period$1,736
    Part B (medical)Doctors, outpatient, equipment$202.90/mo
    Part B deductibleAnnual, before Part B pays$283/yr
    Part D (drugs)Separate plan (or bundled in Advantage)~$0–60/mo
    Medigap (optional)Fills Original Medicare's gaps~$100–300/mo
    💡 Higher income? Watch for IRMAA. If your income two years ago was above roughly $109,000 (single) or $218,000 (married filing jointly), you'll pay a surcharge on Parts B and D. If your income has dropped since (for example, because you retired), you can appeal with form SSA-44. Many people overpay because they don't know they can appeal.

    The whole phrasebook

    Every dotted-word definition, A to Z. Tap one to expand it.

    whenim65.com is an educational site, not insurance, legal, or financial advice, and is not affiliated with the U.S. government or the federal Medicare program. Rules and dollar amounts change every year. Reliably, every year. Confirm your dates at medicare.gov or with SHIP, your state's free unbiased Medicare counseling program (shiphelp.org). Nobody here earns a commission on anything, which is exactly how we like it.