Retire With Confidence — 2026 Edition
Medicare, Social Security, and the money decisions that decide your retirement.
A 295-page reference on the decisions that come at you between 62 and 75 — Medicare, Social Security, income, taxes and long-term care. It's free, and there's nothing to buy at the end of it.
What's in it
- Medicare: your foundation. The four parts, the seven-month enrollment window, what Medicare covers and the gaps it leaves, Original Medicare against Medicare Advantage, Medigap, and Part D.
- IRMAA and the income traps. The surcharge nobody warns you about, the late-enrollment penalties that never end, and how selling a house or converting an IRA can raise your Medicare premium two years later.
- Social Security. How the benefit is calculated, claiming at 62 against 67 against 70, spousal and survivor benefits, the earnings test, and how much of it is taxed.
- Retirement income planning. Building the income stack, the tax difference between a 401(k), an IRA and a Roth, life insurance in retirement, and where you live changing what you keep.
- Protecting what you have built. Long-term care and the hybrid policies that return your money, where you will live, caring for aging parents, and final expense planning.
- Future-proofing, and the reference material. The annual Medicare review, the decision timeline from 59½ to 75+, a glossary of 60+ terms, a 2026 quick-reference card, and what changed for 2026.
Forty-seven chapters, plus a glossary, a 2026 quick-reference card, and a what-changed summary. Each chapter stands alone, so you can go straight to the one that's worrying you.
Who wrote it
Darin Weidauer — Gerontologist, 22-year U.S. Air Force veteran, independent insurance agent and Registered Social Security Analyst. He's the licensed agent behind this site, and he's independent, which means he's appointed with a number of carriers rather than employed by one. That's worth knowing before you read anything he's written about insurance, so it's on the about page as well.
What happens when you ask for it
We email it. Nothing downloads from this page — check your inbox, and your spam folder if it hasn't arrived within a few minutes.
The optional checkbox on the form below is unticked by default. Leave it that way and you get the book and nothing else — no call, no follow-up sequence. Tick it only if you actually want to talk to somebody.
Where should we send it?
Written and reviewed by Darin Weidauer — licensed insurance agent (NPN 18580338), Gerontologist (USC Davis School of Gerontology), MBA, Registered Social Security Analyst, and 22-year U.S. Air Force veteran.Last reviewed September 2, 2026. Plan availability, benefits and costs change every plan year — verify current details at Medicare.gov or 1-800-MEDICARE.