In this solo presentation, CFP® Craig Wear explains why many IRA millionaires lose tax savings not because their Roth conversion plan was bad, but because they blindly follow an outdated plan. Using a pilot flight‑plan analogy, he shows that even a well‑designed plan can drift off course as assumptions (income, account growth, spouse status, tax rules) change over time. Wear introduces a simple habit: a yearly feedback‑loop review of the Roth conversion strategy after filing the prior year’s tax return. He outlines three critical review questions—whether the conversion pace still reduces future RMDs, whether current income and tax environment match the plan’s assumptions, and whether the overall strategy still meets its goal of minimizing future tax exposure. Based on the updated projection, the plan will be either ahead, on, or behind pace, each prompting a specific action (increase, maintain, or decrease conversions). He emphasizes that the most valuable conversion years are before required minimum distributions (RMDs) begin, and that missing a conversion in a “skip” year can cost millions. To operationalize the habit, Wear provides an RMD calculator linked in the description, which projects RMDs and potential lifetime tax savings using data from over 2,000 clients. The video ends with a call to action to use the calculator and watch a follow‑up video.
Chapters
Most IRA millionaires don't lose tax savings because they made a bad Roth conversion plan. They lose them because they followed a good plan. Because having a Roth conversion plan and being protected by it are not really always the same thing. So in this video, I'm going to show you how following your Roth conversion plan can be the most expensive mistake you make. And the one habit I've used to help over 3,000 IRA millionaires avoid over $10 billion in lifetime taxes. And how to tell exactly what to change to keep your conversion strategy working in your favor. Because if a good plan can still create a bad outcome, something important is missing. So let's say you're flying from JFK in New York to LAX in California. Before takeoff, pilot creates a flight plan that gets you to your destination. But here's what happens when the pilot is just one degree off course. At first, you really can't tell, and it looks like everything's going fine. But over a long enough distance, that one degree deviation makes a really big difference. So instead of arriving at LAX, you maybe wind up 40 miles off in the Pacific Ocean. Not because the pilot made a bad plan, but because Even a good plan only works if the actual journey matches the exact plan. And that's the mistake many IRA millionaires make when they build their own Roth conversion plan. They use the best information available at the time, but over several years of plans in action, the assumptions underneath the plan are constantly changing. Change in income can alter how much room is available for future conversions, and a strategy built around a married couple may look different after one spouse dies. That doesn't mean the original plan was bad. The problem comes from expecting a plan built on old information to keep producing the right answer. And here's how big of a difference that 1 degree makes in a retirement plan. To get a look at where your plan is currently heading, you can put your numbers into our RMD calculator that's linked below. Look, so once you understand how closely following your plan can hold you back, the missing piece becomes much easier to see. Just like a pilot doesn't just create a flight plan and then ignore the instruments until landing, a Roth conversion strategy needs a way to check whether it's still on course. Without that feedback loop, following the plan can create a false sense of security while you slowly drift. Of course, after all, if you've been converting You're converting exactly what the spreadsheet told you to convert. It feels like the strategy's working, but completing the plan and accomplishing the goal are not the same thing. A Roth conversion plan tells you what to do based on what you knew when it was built. A conversion strategy tells you how to respond when reality turns out differently. And that difference is where a lot of lifetime tax savings are either won or they're lost. So that's where this habit comes in. So just like how a pilot keeps checking their route and communicating with air traffic control, we check if the strategy still on course before another year of opportunity disappears. So, what does that actually look like? Well, let's start with the problem the strategy was originally built to solve. Most Roth conversion plans are trying to reduce the amount of money that will eventually remain in the traditional IRA when RMDs begin. But imagine your IRA grows much faster than expected for several years. That's just happened. That sounds like good news, and from an investment perspective, it surely is. The problem is that a larger IRA also means larger future RMDs. So before converting the amount in your spreadsheet, the first question becomes, is my current conversion pace still reducing the future RMD problem at the rate I originally expected and planned? Notice that this is a very different question from, did my account go up or down? One measures performance, the other measures whether the strategy is still accomplishing its objective. Next, imagine the original plan assumed a certain income level. Then you end up taking on some consulting work or a spouse retires sooner than planned. The conversion amount hasn't changed, but the tax environment surrounding that conversion has, which naturally leads to the next question. Does the amount that made sense before still make sense today? Because Roth conversions don't exist in isolation. They stack on top of the rest of your income, and the same thing happens with tax rules. A spreadsheet created several years ago can still look detailed and precise, but if the assumptions inside it no longer match the current tax situation or Medicare threshold, the precision becomes actually very misleading. And that's why the review asks, am I still using current numbers to make current decisions? And finally, after updating everything, there's one question that matters more than all the others. Is this strategy still producing the future outcome it was designed to create? Because the goal is not to convert money. The goal is to reduce future tax exposure. A conversion strategy should be judged by the problem it removes, not the transaction it completes. So once those questions have been answered, the next step becomes surprisingly simple. The updated projection will usually tell you one of three things. You're ahead of pace. You're on pace, or you're behind pace. And each outcome naturally points toward a different decision. If the strategy is still on pace, well, there, you won't need to change much. If the future tax problem is growing faster than expected, the strategy you might want to consider larger or earlier conversions. And if circumstances have shifted in the other direction, reducing or delaying a planned conversion may actually be your better move. That's why this review works best after a prior year's tax return has been completed, if you can wait that long. At that point, the assumptions have been replaced by actual numbers while there's still enough time left in the current year to adjust the strategy. Because the most valuable years for Roth conversions are the ones before RMDs begin. Medicare costs rise and you're able to take advantage of the filing joint thresholds. But once those years pass, the opportunity to reduce the tax burden is gone. So don't make the habit to do a Roth conversion every year. Make the habit, check the Roth conversion plan to make sure you're keeping pace before another year of opportunity disappears. That's the habit that we help our clients with. So hopefully they keep their plan up to date and actually arrive at their destination. So to easily check if you're keeping pace with Roth conversion plan, you can put your own numbers into our RMD calculator that's linked below. It helps you project your RMDs and gives you a clear idea of what you could save in lifetime taxes based on over 2,000 of our actual clients' results. And if your plan is telling you to skip a Roth conversion this year, you could be making a million-dollar mistake. So to make sure you're on the right track, go Watch this video next.
