The Real Numbers at 55, 60, and 65 — and the People Who Should Skip It Entirely Wednesday, August 19, 2026 · Money & Care Planning · 10 min read Last month we laid out the $100,000 question Medicare won’t answer: roughly seven in ten people turning 65 today will need long-term care, Medicare doesn’t…
The Honest Math Wednesday, August 12, 2026 · Money & Housing · 10 min read The brochure is genuinely seductive. Resort-style pools, a golf course out the back door, pickleball and a hundred clubs, a clubhouse humming with people your own age, and someone else mowing the lawn and shoveling the snow. After Monday’s piece…
Going Back to Work by Choice — and What It Does to Your Benefits and Taxes Wednesday, August 5, 2026 · Money & Work · 10 min read On Monday we made the case for the encore — that purpose is medicine, and that going back to work in the third age is increasingly a…
How to Defuse It on Your Terms — Before the IRS Sets Them Wednesday, July 29, 2026 · Retirement & Taxes · 10 min read Everything we write on Wednesdays comes back to one idea: the second half of life is not something that happens to you — it is something you design. Nowhere is…
The $100,000 Question Medicare Won’t Answer — and the Four Ways People Actually Cover It Wednesday, July 22, 2026 · Money & Care Planning · 11 min read Start with the number that reorganizes everything: a person turning 65 today has a roughly 70 percent chance of needing long-term care before they die, and just…
What’s Worth Buying in Safety Tech After 55 — and What’s Junk Friday, July 17, 2026 · Technology · 10 min read This is the third article this week about living on your own terms, and it is the one where we finally go shopping. On Monday we made the argument that solo aging is…
The Real Math of the Claiming Decision After 55 By The Bold & The Wise Editorial Team Wednesday, July 1, 2026 · 11 min read Categories: Legal, Money & Family, Wednesday Editor’s note: A standalone piece on one of the three largest financial decisions adults face in the second half of their lives. The guidance…
Rebuilding Your Charitable Giving Plan By The Bold & The Wise Editorial Team Wednesday, June 17, 2026 · 10 min read Categories: Legal, Money & Family, Wednesday Part three of The Divorce Reset — a four-week practical guide to rebuilding your financial life after divorce. Editor’s note: This article is the third in a four-part…