Craig Wear, CFP®Craig Wear, CFP® | Expert in Roth Conversions & Tax-Efficient Retirement Strategies for IRA Millionaires

Are You Minimizing The WRONG Taxes?

11 Mar 2026 · 1 min

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In this segment, Craig Wear, CFP®, explains that many IRA investors work with skilled CPAs who excel at minimizing taxes on a year‑by‑year basis. He challenges viewers to consider a different objective: minimizing taxes over a lifetime rather than just the current year. Because CPAs are typically trained to solve for a single tax year, their strategies may appear conservative and responsible in the short term but can actually increase total tax liability across decades. Wear argues that a strategic Roth conversion plan must be designed with a multi‑decade horizon, and that short‑term tax‑saving tactics can unintentionally raise lifetime taxes.

Chapters

Most IRA millionaires I meet are working with a very good CPA. They're organized, they're careful, they help you minimize taxes every single year, and that's important. But here's the question almost no one asks: are you minimizing this year's taxes or your lifetime taxes? Because those are two very different objectives. Your CPA is trained to solve for one year at a time, maybe the next one. A strategic Roth conversion plan, on the other hand, has to look at decades ahead. And when you zoom out, something surprising happens. Strategies that look conservative, even responsible on this year's return, can quietly increase what you pay over the rest of your life.