Jay Thompson

Image titled "Choosing a Medicare Supplement (MNedigap) plan"
  • Jay Thompson
  • Posted by Jay Thompson
March 14, 2026

How to Choose the Right Medicare Supplement Plan

A practical guide to filling the gaps in Original Medicare and tips...

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  • Jay Thompson
  • Posted by Jay Thompson
March 1, 2026

The Hidden Side of Retirement: Boredom, Identity, and Marriage

Retirement planning conversations usually orbit around money. Net worth. Withdrawal rates. Social...

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  • Jay Thompson
  • Posted by Jay Thompson
February 22, 2026

Healthcare Before 65: The Gap Years Nobody Plans For

Quick Summary: If you retire before 65, Medicare isn’t there yet —...

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  • Jay Thompson
  • Posted by Jay Thompson
February 17, 2026

Why Your Tax Rate in Retirement Might Be Higher Than You Think

Quick Summary: Retirement doesn’t automatically mean lower taxes. While earned income may...

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  • Jay Thompson
  • Posted by Jay Thompson
February 12, 2026

Medicare Advantage vs. Supplement: What Changes at 75?

Quick Summary: Both Medicare Advantage and Original Medicare with a Supplement can...

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  • Jay Thompson
  • Posted by Jay Thompson
February 5, 2026

How Social Security Is Taxed (And Why It Surprises People)

Quick Summary: Social Security isn’t automatically tax-free. Depending on your total income,...

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  • Jay Thompson
  • Posted by Jay Thompson
February 4, 2026

The Retirement Paycheck: How to Turn Assets into Monthly Income

For forty years, most of us had a simple system. Work →...

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