Mark your enrollment window
Write down the seven months in your Initial Enrollment Period and check whether enrollment may be automatic or requires action through Social Security.
Free · 2026 edition · 5 pages
Your first Medicare decisions, in the right order.
A plain-English checklist for people approaching 65, people working past 65, and family members helping with Medicare — checked against Medicare.gov, CMS, and SSA.
- Map the 7-month Initial Enrollment Period
- Check job coverage, COBRA, HSA, Part D, and Medigap timing
- Compare Original Medicare and Medicare Advantage without a sales pitch
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Source-checked Aug. 28, 2026
Independent education
No plan sales
Not affiliated with Medicare or CMS
Inside the notebook
Five pages built around the decisions that change your timing.
This is a focused starting guide, not a promise that every Medicare situation fits one checklist.
Check the coverage you already have
Working past 65, COBRA, retiree coverage, and an HSA can change which questions you must answer before enrolling.
Compare the two main coverage paths
See the practical questions behind Original Medicare and Medicare Advantage: providers, drug coverage, prior authorization, supplemental coverage, and travel.
Source check: Medicare.gov says the Initial Enrollment Period generally lasts seven months; current-employment coverage may create an eight-month Part B Special Enrollment Period; COBRA does not extend it; and going 63 days or more without Medicare drug coverage or other creditable drug coverage may lead to a lifetime Part D late-enrollment penalty. See the official pages for enrollment timing, working past 65, COBRA, and creditable drug coverage.
Who it is for
Not only for someone having a 65th birthday.
The checklist begins with turning 65 because timing mistakes are common there, but it also helps spouses, caregivers, people still working, and anyone revisiting how Medicare fits with other coverage.
Is this personalized insurance advice?
No. It is general educational information. It does not recommend a company or plan and is not medical, legal, tax, or insurance advice. Use Medicare.gov, Social Security, your benefits administrator, a licensed professional, or your local SHIP for help with your circumstances.
Will you sell my information to an insurance agent?
No. The Medicare Notebook does not sell Medicare plans, and the form is not a lead transfer to an agent or broker.
What emails will I receive?
The checklist immediately, then two short educational emails: one about working past 65, COBRA, and HSA timing; one about comparing Original Medicare and Medicare Advantage. After that, only occasional source-checked updates. Every email includes an unsubscribe link.
How current is it?
The checklist and landing-page claims were cross-checked on August 28, 2026 against current Medicare.gov, CMS, and SSA material linked on this page and inside the PDF.