Jay Thompson

Image with large print: "Starting retirement planning late?" And smaller print with "Here's How to Catch Up"
  • Jay Thompson
  • Posted by Jay Thompson
March 9, 2026

Starting Retirement Planning Late? It's not too late to catch up

Every now and then, someone sends me a question that begins with...

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  • Jay Thompson
  • Posted by Jay Thompson
February 28, 2026

Cardiac Health after 50: Lessons from a Widowmaker Survivor

At 51, I had a heart attack.Not a “maybe indigestion” scare. The...

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

Social Security Claiming Strategies: Yes, Age Matters

Bottom line: When you claim Social Security is one of the few...

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  • Jay Thompson
  • Posted by Jay Thompson
February 16, 2026

Income Withdrawal Strategy: Turning a Portfolio Into a Paycheck

Short version:Retirement income isn’t about “taking 4% and calling it a day.”...

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

Medicare: Get the Timing Right (Or Pay for it Later)

Short version:Medicare isn’t complicated. The calendar is. Miss a window, misunderstand your...

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  • Jay Thompson
  • Posted by Jay Thompson
February 7, 2026

Taxes: Roth Conversions

Roth conversions are simple in concept and tricky in execution. You move...

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

Taxes: Roth Conversions

Roth conversions are simple in concept and tricky in execution. You move...

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

Explore the Six Pillars

Retirement isn’t a single decision. It’s a structure. When I retired at...

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  • Jay Thompson
  • Posted by Jay Thompson
January 25, 2026

Lifestyle Pillar: Start Here

You did not retire just to optimize spreadsheets. You retired to live....

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

Healthcare Pillar: Start Here

If Medicare is the policy manual, healthcare is the lived experience. This...

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