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The Turning-65 Decision Workbook

Our free articles tell you how Medicare works. This tells you exactly what to do: your personal deadline calculator, the comparison tables for real quotes, and the word-for-word scripts for HR, brokers, pharmacies, and hospitals. Print it, fill it in with a pen, hand pages to your spouse.

$24 one-time · instant PDF download Get the workbook
  • Instant PDF download
  • Print at home or type in it
  • Free update when 2027 numbers publish
  • Stuck? Email us, a person answers

Not sure? Download three sample pages first, free. The cover, the dates calculator, and the broker conversation card, exactly as they appear inside.

2026 edition. Updated editions ship free to past buyers when CMS changes the numbers. If cost is a genuine barrier, write to us and we'll sort something out.

24 pagesletter-size, print-first design
9 worksheetswith write-in tables, not paragraphs
8 scriptsword-for-word, including the wallet card
2026 figuresofficial CMS amounts, sourced

What's inside

Six parts, front to back, in two sittings

Part one

Your dates

The personal deadline calculator: write your birthday month once, derive your enrollment window, your gap-free deadline, your Medigap window's exact closing date, and the still-working exit clocks.

Part two

Your situation

Doctor and medication inventories built for the plan finder, plus the budget-and-temperament page that settles the fixed-cost vs. pay-as-you-go question honestly.

Part three

The decision

The path scorecard that turns your worksheets into a defensible choice, the tiebreaker rule, and the HSA shutdown worksheet with the six-month math done for you.

Part four

Shopping

Side-by-side tables for three Medigap quotes (with the rating-method question most buyers never ask), two Advantage finalists, three drug plans, and the safe switching order for later years.

Part five

Scripts

The HR email requesting the 20-employee answer in writing. The five broker questions with red flags. The pharmacy counter lines. The IRMAA appeal worksheet. The hospital wallet card you cut out and carry.

Part six

Forever pages

The September ANOC ritual, the 30-minute annual re-shop with its receipt table, the 2026 numbers card with a write-in column for 2027, and the done list.

Actual pages

Worksheets, not walls of text

Workbook page: the personal deadline calculator with write-in date table
The deadline calculator: your six dates, derived from one birthday.
Workbook page: the path scorecard comparing Original Medicare and Medicare Advantage
The path scorecard, with the one-way-door tiebreaker.
Workbook page: the HR email script and the cut-out hospital wallet card
The HR email and the hospital wallet card you cut out.

Fair questions

Why pay, when the articles are free?

Because they're different jobs. The free site explains and recommends; it will stay free, all of it, forever. The workbook is the execution layer: your dates on paper, your quotes in one table, the exact sentence to say at the hospital intake desk. If you can build all that yourself from our articles, genuinely, do that. This is for everyone who'd rather spend $24 than an evening with a legal pad.

What format is it?
A 24-page PDF, letter size, designed for printing. It reads fine on a tablet, but it's built for a pen: write-in tables, checkboxes, and one page you literally cut with scissors.
Is it up to date?
Every figure is an official 2026 amount published by CMS, checked July 2026, with sources printed on the numbers page. When CMS publishes 2027 figures this fall, buyers get the updated edition free.
Is this financial or insurance advice?
No. It's an educational organizing tool from an independent publisher. It makes you the best-prepared person in the room with a licensed agent or free SHIP counselor; it doesn't replace them for plan-specific decisions.
What if it's not useful to me?
Reply to your receipt within 30 days and we'll refund it. We'd rather refund $24 than have someone resent the purchase.
I'm helping a parent. Does it work for that?
Yes, and honestly that might be its best use: fill it out as them, then bring it to their kitchen table. The worksheets give the two of you something concrete to point at.

The guarantee, in plain English: if the workbook doesn’t make your decision easier, email us within 30 days and we refund the $24 in full. You keep the PDF. No form, no questions, no restocking fee on a file.

Before you buy

The questions buyers ask first

How do I get the workbook after paying?
Checkout takes about a minute; the download link appears immediately and arrives by email, so you can save the PDF to your computer, tablet, or phone. If anything goes sideways, email us and a person sorts it out.
Do I need a printer?
No. The workbook works both ways: print the whole thing (24 pages, black and white is fine) and fill it in with a pen, or type directly into the PDF on a computer or tablet and save your answers.
Is it up to date for 2026, and what about 2027?
Every figure is the official 2026 amount, checked against CMS publications. When CMS releases the 2027 numbers each fall, we update the workbook and email buyers the new edition free. The forever pages include a write-in column for next year’s figures.
What if it doesn’t help me?
Email us within 30 days and we refund the full $24, no questions, and you keep the PDF. If cost itself is the barrier, write to us anyway; nobody gets turned away over $24. (The formal refund policy, equally short.)
Is this insurance advice? Will you try to sell me a plan?
No and no. The workbook is educational: it organizes your dates, costs, and decision so any conversation you have with Social Security, HR, or a broker happens on your terms. We don’t sell insurance, and no company pays us to steer the worksheets.

Ready when you are

One decision. One workbook. Done right once.

Not sure Medicare's even confusing enough to need this? Run the free decoder first. If your situation turns out simple, believe us, we'll say so.

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