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Fresh Takes on the Decisions That Matter
Timely posts on Medicare, retirement, estate planning, and tax strategy. Updated regularly — bookmark this page or check back each season.
Medicare 2026: What's New This AEP
Premium changes, the new $2,000 Part D cap, and what to re-shop this October
The 2026 Annual Election Period brings the biggest Part D change in over a decade plus standard premium adjustments. Here's what to know before October 15.
Read postThe 2026 Estate Tax Sunset
The federal exemption could drop by half on January 1, 2026 — what families with $5M-$15M should do now
The federal estate tax exemption is scheduled to drop from $13.99M to roughly $7M per person on January 1, 2026 unless Congress acts. For families in the gap, the planning window is now.
Read postBackdoor Roth IRA: Step-by-Step for High Earners in 2026
How to fund a Roth IRA when your income exceeds the limits — without triggering the pro-rata rule
If your income exceeds $150K (single) or $236K (joint), you can't contribute directly to a Roth IRA. The Backdoor Roth is the workaround — but the pro-rata rule trips up most who attempt it.
Read post5 Estate Planning Mistakes That Cost Families Six Figures
The quiet errors that wreck good plans — and how to avoid each one
Estate plans don't fail because of bad attorneys. They fail because of small administrative errors that nobody catches until it's too late. Here are the five we see most often.
Read postHow to Read Your Social Security Statement (And Spot Mistakes)
What each number actually means, and the common errors that cost retirees real money
Your Social Security statement contains numbers that will determine the largest source of retirement income for most Americans. Most people glance at it and file it. Here's how to actually read it.
Read postYear-End Tax Moves for Business Owners: A December Checklist
10 actions to take before December 31 — most are worth $5K-$50K in tax savings
Most business owners realize too late that the biggest tax savings happen BEFORE December 31, not at filing in April. Here's the checklist.
Read postShould You Pay Off Your Mortgage Early?
The math says one thing. Behavior often says another. Here's how to think about it.
It's one of the most common questions in personal finance — and one of the most polarizing. The math has a clear answer at most interest rates. Behavior has a different one.
Read postTax-Loss Harvesting: Use Losses to Lower Your Bill
A practical guide to harvesting investment losses — including the wash-sale rule that trips up most DIY-ers
Tax-loss harvesting is one of the most-recommended tax strategies — and one of the most commonly bungled. Here's how to actually do it right.
Read postCash Balance Plans: The Best-Kept Secret for High-Income Owners
How profitable business owners shelter $150K-$280K+ per year on top of a 401(k)
For high-income business owners over 45, the Cash Balance plan is the highest-leverage tax shelter in the U.S. tax code. Most owners have never heard of it.
Read postPension Lump Sum or Annuity? A Framework for Auto Retirees
The crossover-age math, longevity considerations, and what to factor in beyond the headline numbers
It's one of the largest single financial decisions of your life — often worth $300K-$1M+. Yet most retirees make it in a single afternoon with their pension paperwork. Here's the framework we use.
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