The Financial Harmony™ Podcast

Will High Earners Actually Pay Less Tax in Retirement?

High earners are often told they’ll be in a lower tax bracket in retirement.
For executives and business owners, that promise rarely holds up.

In this episode of the Financial Harmony™ Podcast, Dr. Preston Cherry breaks down why retirement taxes are often higher—and more complex—than people expect. While income may decline, taxable income often doesn’t, due to RMDs, taxable Social Security, Medicare IRMAA surcharges, and capital gains.


In this episode:

  • Why “lower” doesn’t always mean low for high-income retirees.
  • The hidden tax layers most retirement plans underestimate.
  • Why retirement income is often lumpy, not smooth.
  • Practical strategies for lifetime tax smoothing and withdrawal sequencing.


Segment highlights:

  • The Wealth Word: Why the “low-tax retirement” idea persists
  • The Signal: Cutting through noise, headlines, and false certainty in retirement planning
  • The Money Move: How tax brackets really work in retirement and what to plan for instead
  • Financial Harmony™: The financial and emotional investment we make in adult children—and how to audit it without guilt
  • Culture Corner: Why this podcast paused, and how alignment—not hustle—brought it back


🎯 Start here:

Take the Gen X Retirement Readiness Scorecard
https://concurrentfp.typeform.com/genx-scorecard


Go deeper:

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@DrPrestonCherry