In this presentation, Craig Wear, CFP®, uses a chess analogy to explain why the timing of a Roth IRA conversion is critical and why a rushed December conversion often misses major value. He identifies five essential “pieces” that must be positioned before the conversion move: the Rook (your CPA) – whose early involvement before tax‑season overload enables proper coordination of estimated payments and conversion timing; the Bishop (your investment advisor) – who evaluates which holdings are best to convert by looking diagonally at portfolio recovery potential; the Knight (your estate attorney) – who assesses how moving money from pre‑tax to post‑tax changes inheritance and beneficiary outcomes; the King (your spouse) – whose awareness and participation protect the household’s long‑term retirement strategy; and the Queen (timing) – the most flexible piece that must be given space to align market conditions, income levels, and tax brackets throughout the year. Wear argues that waiting until December ignores these preparatory steps, often resulting in lost tax savings and missed market opportunities, with potential value on the order of $500 K–$1 M. He concludes with a call to a masterclass for deeper guidance.
Chapters
A Roth conversion isn't something you do in an afternoon in December, click a few buttons and call it good. Just like in chess, the conversion itself may be one move, but the value comes from where all the pieces were before that move was made. And every strong conversion plan I've ever studied has really these 5 pieces that are sitting in a good position. The first piece is your rook. And if you played chess, you know that the rook can move as far as it wants to in a single move, but early in the game, it's stuck behind the pawns. So it's not much help until the pawns actually have gotten moved out of the way. And that's what happens maybe from February through April, because that rook is maybe your CPA. During tax prep season, your CPA is buried in filings, deadlines, extensions, client returns. So if you want to coordinate estimated payments, withholding, and conversion timing properly, you need to move that piece into place and have that conversation way before they get swamped. If you miss that window, you might end up having to wait until next year or do something in a very rushed manner. The second piece is, we'll call it like your bishop, which can move diagonally across the board. It spots lines that aren't obvious if you're only looking straight ahead. And Roth conversions work the same way. Most people look at how much they should convert, but the bishop looks at what makes the most sense to convert. The bishop is, we'll call it your investment advisor. They look at which holdings are down. Which assets have the strongest recovery potential and how it really impacts the rest of your portfolio and your conversions. Those are diagonal questions and identifying the right assets takes real evaluation across your portfolio and it needs time. It's not a decision you want to rush until the beginning of December, like most people do, because by then kind of the cake's already baked on the investment stuff and you lose out so much opportunity that you could have had, had you started earlier. The third piece that we'll call it is your night. This piece, a lot of people just simply overlook because until all of a sudden it suddenly changes everything because It doesn't move like anything else on the board. It doesn't go straight or diagonal. It jumps. And for your Roth conversion strategy to be truly solid, you need to plan for those jumps because when you convert, you're not just moving money from one retirement account to another, you're moving it from pre-tax to post-tax. And that move changes how that money behaves in the future in ways most people don't really expect. And that's maybe where your estate attorney comes in because when your assets change, it could affect how assets are inherited, how beneficiaries experience the money and whether the documents you already have still do what you think they do or what you want them to do. So before you do a conversion, your broader estate plan may need just a quick review as well. And look, that's especially crucial when it comes to the next piece, which is your king. In chess, the king is the piece the entire strategy is built around protecting. He can only move one square at a time. So when he gets cornered, there's not much at all he can do. So you don't win by ignoring the king or leaving him exposed, and you definitely don't win by bold moves on one side of the board while the king is vulnerable on the other side of the board. Roth conversion planning has the same issue. A strategy can look great on paper and still fail if the person most affected by the long-term consequence isn't taken into consideration. Because this isn't just about one tax year, it's about your whole retirement. It affects all your retirement income, household confidence, and what happens once you're gone. We're going to call the king as your spouse. The sooner your spouse is not just aware of the plan, but part of the decision, The more confidently the whole thing gets executed. I've seen more plans stall because of a spouse who wasn't in the room than for almost any other reason. And finally, there's the queen. It's the most flexible piece on the board. She can move in multiple directions. She can create great advantage, but only if she has the space to move. And if you rush her into the fray, your opponent will take her out before you had a chance to create that advantage. If the board is cramped or the other pieces are in her way, the queen's power is limited. And Roth conversions are exactly that. The best opportunity may not show up in December. In fact, probably will not. show up in December. It may show up when markets are temporarily up or down for each of the securities that you have. And when your income is lower than you expect, or when projections show there's still room in the current bracket, but you only get to use that opportunity if the rest of the board is ready. The queen is timing. Instead of assuming the right moment to convert is December, use timing to your advantage can make a massive difference. It lets you see when market conditions and your tax positioning actually line up and You can only spot those when you have a full year to monitor and to act. What so many people do in Roth conversions is totally contrary to what got them to the success in the first part. Even advisors or CPAs will say, hey, just wait till December. We'll play cleanup. We'll figure it out. Look, our research has proven that December is actually the worst time of the year to convert if you consider all these different factors. And if you wait too long, the IRS will have moved their piece across the board and trap you. And if you move pieces into place in preparation, you're in a whole lot better position for checkmate.
Hey, if you're an IRA millionaire, you know, what matters in doing Roth conversions isn't just how much you convert, it's also the timing of when you get— when you convert. And there's as much as $500,000 on the table, could be even $1 million if you don't get those details right. And I know there's all kinds of messages all over the internet and there's, you know, you can scroll through your socials and you get 10 financial advisors telling you to convert, not to convert, how fast, how not. Look, the facts are just the facts and the math is undeniable. I've got a masterclass. I'd like to walk you through all the details of it. I don't think that you'll find anything in there that you would probably disagree with. Our client list includes tax attorneys, CPAs, financial advisors, and a whole lot of really bright engineers who knew the math and decided to come and allow us to help them anyway. But I just want you to get the information. I want you to get to the masterclass, learn what you can get accomplished, and click the button below and see what happens.
