The House Is the Hard Part
Most families get the will right and the house wrong. One decision — made years early, out of kindness — can cost your children a six-figure tax bill.
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Four Moves You Have Until December 31 to Make
I’m not a CPA, a tax attorney, or a financial advisor, and none of this is personal tax advice. Tax rules turn on details that are specific to you — your income, your state, your filing status, your accounts. Every figure here is sourced and current as of publication, but use this to build a…
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The Envelope You’re About to Throw Away
It arrives this month, it looks like junk mail, and ignoring it is the most expensive thirty seconds of your year.
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Medicare, Explained Once and Properly
Medicare’s Annual Enrollment Period runs October 15 through December 7, and by the time it opens, most readers will have already made — or drifted into — the single decision that shapes nearly everything else about their healthcare for years to come. This piece exists so that decision is made on purpose. We’re going to…
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The Beneficiary Audit
The Hour That Quietly Overrides Your Will Wednesday, August 26, 2026 · Estate Planning & Wills · 9 min read In July we walked through the five documents of a solid estate plan — the will, the powers of attorney, the healthcare directive, the HIPAA release. If you did that work, you may feel finished….
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What Long-Term Care Insurance Actually Costs
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…
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Are 55+ Active-Adult Communities Worth It?
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…
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Unretirement, by the Numbers
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…
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The Retirement Tax Bomb
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…
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Paying for Long-Term Care
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…
