The biggest tax wins happen years before the return is filed
Most tax conversations with clients happen in the spring, when the numbers are already fixed and the only question left is how to report them. Justin opened the session by reframing where the leverage actually sits. By filing season, the decisions that move lifetime tax, when to convert, how much, which accounts to draw from, and how to keep income under the thresholds that trigger surcharges, have already been made or quietly missed. The work that moves the needle is multi-year positioning done in advance, not deductions found in April. The session walked through what that positioning looks like when you can see its effect on the whole plan at once, rather than one tax year at a time.
Roth conversions, sized to the plan
A Roth conversion is one of the few levers that lets an advisor decide, deliberately, how much income to recognize in a given year. The skill is in the sizing. Convert too little and you leave low-bracket room unused; convert too much and you spill into a higher bracket, or trip a Medicare surcharge two years out that costs more than the conversion saved. Justin showed how to size a conversion against the brackets a client will actually occupy over the rest of retirement, not just this year's, so the decision compounds correctly across the plan. The window that opens in the gap between retirement and the start of required distributions is often the most valuable stretch a plan has, and the value comes from filling brackets on purpose across several of those years rather than reacting one return at a time. The full framework is in the Roth conversion strategy guide.
IRMAA: the surcharge that responds to income from two years ago
IRMAA, the income-related monthly adjustment amount, is the surcharge added to a client's Medicare Part B and Part D premiums once modified adjusted gross income crosses a threshold. The detail that catches people is the timing. The premium a client pays in a given year is set by the income they reported two years earlier, so a large Roth conversion or capital gain today does not raise this year's Medicare premium. It raises the premium two years out, which is exactly when a client who was not warned will be surprised by it. Because the thresholds are cliffs rather than gradual phase-ins, a single dollar of income over a bracket line can add hundreds of dollars in annual surcharge per spouse. The planning move is to position income around those thresholds on purpose, with the two-year lag built into the timeline, so a conversion that makes sense on its own is not undone by a surcharge later. The IRMAA brackets guide has the current thresholds.
The decisions advisors miss
The session's title points at the moves that rarely show up in a return-season review because they are not about the current year at all. Withdrawal sequencing, which accounts a client draws from and in what order, changes the trajectory of taxable income for the rest of the plan. Bracket management across multiple years turns a string of unremarkable returns into a deliberately lower lifetime bill. Coordinating conversions, capital gains, and the start of Social Security and required distributions so they do not collide in the same years is the kind of work that only becomes visible when you can model the whole horizon at once. None of it is exotic. It gets missed because most planning tools show one year at a time, and the needle moves across many.
What it looked like live in Income Lab
The back half of the session moved into the software, where Justin worked the decisions live in Tax Lab. He showed a multi-year view of a client's income and tax picture, sized a Roth conversion against the brackets and the IRMAA thresholds on the same screen, and traced how a change in one year flowed through to the spending number, the surcharges, and the lifetime tax total. The point of working it live, rather than on slides, was to show that the analysis is inspectable: an advisor can see where every dollar of recognized income lands and what it costs or saves, which is what makes the multi-year case credible to a client. He also showed where Penny, the Income Lab paraplanner, surfaces positioning moves an advisor might otherwise have to go hunting for. For advisors who are new to the platform, the section below has the fastest way to get up to speed, and a walkthrough on your own client numbers is one click away.
