Roth Conversions for High Earners: Timing, Taxes, and Long-Term Control (Ep. 23)

Retirement tax decisions often feel simple on the surface, but the ripple effects can last decades. The real question is not whether taxes will be paid, but when, how, and by whom.

In this episode, Dan Reese, CFP®, walks through how Roth conversions, a taxable event, can fit into a broader retirement and estate plan for high-income earners. He explains when conversions may help manage future tax exposure, Medicare premiums, and inherited IRA issues. The conversation also covers market downturns, early retirement gap years, state tax differences, and why scenario planning is essential before acting.

Key takeaways:

• How Roth conversions can affect heirs, estate plans, and long-term family tax outcomes over multiple generations
• Why higher income does not automatically rule out conversions, and how added income can trigger hidden taxes
• How market downturns may lower the taxable cost of converting retirement assets
• Why early retirement gap years can create valuable planning windows before Social Security begins
• How moving between low-tax and high-tax states can change the timing and value of conversions
• And more!

Resources:

• Carson Wealth Retirement Readiness Quiz

Connect with Dan Reese CFP®:

• Avery Wealth
• LinkedIn: Avery Wealth
• LinkedIn: Dan Reese