Medicare rewards the organized. Here is the month-by-month version of organized, starting six months out, with each task small enough to finish over one cup of coffee.
Six months before your birthday month
- Confirm your work-quarter status at ssa.gov: 40 quarters means premium-free Part A. Spousal records count.
- Decide the employer question. Still working with group coverage from a 20+ employee company? You may delay Part B penalty-free. Smaller employer, COBRA or retiree coverage? Different rules entirely, and this is the month to learn them.
- Start the doctor and drug list. Two columns on one page: physicians you keep, prescriptions with dosages. Every good decision downstream uses this page.
Four months out
- Learn the two stacks. Read our four parts lesson and the Advantage vs Medigap framework. One hour total.
- Rough your budget. Part B costs $202.90 a month in 2026; higher incomes add IRMAA. Know your bracket before plans start quoting you.
Three months out (your IEP opens)
- Enroll in A and B at ssa.gov if you are not delaying B. Enrolling in these three months gives you a clean start on the first of your birthday month.
- Get real quotes. With your doctor-and-drug page, have every option priced for your county. This is precisely the work we do free.
Two months out
- Choose your stack and apply. Advantage plan, or Medigap plus Part D. If Medigap tempts you at all, remember your six-month no-health-questions window starts with Part B; use it.
- Coordinate HSA contributions if you have one; contributions must stop before Medicare begins, and Part A can backdate.
One month out
- Confirm cards and start dates. Medicare card, plan card, pharmacy on file.
- Book post-birthday appointments under the new coverage, including the free Welcome to Medicare visit.
Birthday month
- Celebrate, covered. Then set one recurring calendar reminder: every October 15, review the plan. Plans change annually; your loyalty should be earned annually.
The two mistakes this calendar prevents
Missing the IEP entirely (a lifetime Part B penalty of 10 percent per year missed) and skipping drug coverage because you feel healthy (a permanent Part D penalty of 1 percent per month). Both are unforced errors, and both are why the six-month head start exists.
Class dismissed
Questions about how this applies to you? That is what office hours are for: call (561) 770-7957 or book a free review. No cost, no pressure, ever.
