One overlooked retirement expense can quietly unravel even the most carefully built plan.

In this episode, Charles discusses common retirement pitfalls, including healthcare coverage gaps before Medicare, unexpected expenses, Social Security taxation, and the ripple effects of RMD decisions. He explores why retirement planning involves more than investments alone and discuss the role of income, tax, healthcare, and estate strategies. The conversation also covers the growing use of AI in retirement planning, the importance of personal context, and common misconceptions about annuities. Plus, learn how seemingly simple financial decisions can trigger unexpected tax and Medicare consequences years later.

Hear The Tax Smart Retirement show every Sunday at 6am WAMJ 107.5/97.5 Powered by The Rollover Company.

For more information and to schedule a complimentary consultation with Charles Winfrey, visit www.Rollovercompany.com.