What if planning forward is the wrong way to retire?

This episode flips the script on traditional retirement planning by exploring a “reverse engineering” approach, starting with your end goal and working backward to build a strategy. The conversation breaks down why relying on investments alone can miss key factors, and how taxes, income timing, healthcare, and estate planning all intersect. It also tackles common misconceptions about lower taxes in retirement, the risks of stacked income streams, and why Roth conversion decisions go beyond simple calculators. The focus stays on building a comprehensive plan that aligns with real-life goals, not just numbers on a page.

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.