Roth Conversions
Fiduciary Retirement Planning
The Tax Decision With A Closing Window.
A Roth conversion moves money from a traditional, tax-deferred account into a tax-free Roth. You pay the tax this year so you (or your heirs) don't pay it later, often at a higher rate. The math sounds simple. The execution isn't. The conversion window is widest in the years between retirement and age 73, when you've stopped earning W-2 income and haven't started Required Minimum Distributions. Convert too little during that window and you leave a traditional IRA building toward an RMD problem. Convert too much and you push yourself into a higher bracket today, or trigger an IRMAA surcharge two years from now.
We model your conversion window every year. We identify the years where your income creates the most room to convert efficiently, without triggering Medicare premium surcharges or creating a future tax problem that undoes the work. The goal isn't to convert the most. It's to pay the least tax over your lifetime, not just this year.
WHO THIS IS FOR
Built for Retirees With Large Traditional IRAs.
Clients with $500K+ across IRAs, 401(k)s, and other tax-deferred accounts, who are between retirement and age 73 (and especially those still 5+ years from RMDs starting). If you have a large traditional IRA building toward a future RMD problem, a Roth balance that's underfunded relative to your traditional balance, and no clear plan for how much to convert in any given year, this is the conversation to have. Particularly valuable when paired with the years between retirement and Social Security claiming, where your bracket is temporarily low.
Pillars of Your Conversion Strategy
A Roth conversion isn't one decision. It's a series of annual decisions made against a multi-year picture. Here's how we handle each layer.
The Conversion Window
The years between retirement and age 73 are usually the best years to convert. You've stopped earning W-2 income but haven't started RMDs. Your bracket is often lower than it was during your peak earning years and lower than it will be once Social Security and RMDs are flowing in together. The window is real, but it's not the same for every household, and it's not always open the whole time. We map your specific window against your specific bracket, year by year.
Multi-Year Modeling
A one-year Roth conversion decision is almost never the right way to look at the question. The conversions you do (or don't do) between age 60 and 73 affect your tax bill every year from then on. Convert too aggressively and you pay more tax in the conversion year, plus possibly trigger IRMAA surcharges two years later. Convert too conservatively and you leave a traditional IRA building toward an RMD that arrives in your highest tax brackets. We model the next ten to fifteen years, not just this one.
IRMAA & Bracket Coordination
Every Roth conversion is also an income event. It fills up your current tax bracket and counts toward the IRMAA threshold that determines your Medicare premium two years from now. A conversion that looks tax-smart in isolation can become expensive when you account for the bracket-filling effect and the IRMAA cliff. We model the full picture before any conversion decision: this year's tax bill, this year's bracket, the IRMAA implication two years out, and the RMD trajectory ten years out.
Let's Build Your Conversion Plan
On your Retirement Coordination Review, Jonathan reviews your traditional IRA balance, your projected RMD trajectory, and your conversion window. Then we show you what a multi-year conversion strategy could look like for your situation. No pressure. No product pitch. Just clarity.
Layer 01
Annual Conversion Sizing
The amount you convert in any single year is driven by your bracket, your IRMAA exposure, and your projected income. We size each year's conversion to fit your specific situation, not to a fixed formula.
Layer 02
Lifetime Conversion Strategy
Annual conversion decisions are the tactical layer. The strategic layer is the multi-year plan: how much total to convert across the window, in what order, and how that interacts with your Social Security timing, your retirement income strategy, and the RMD problem you're solving for.
Two layers. One coordinated conversion strategy. The work that turns a tax decision into a multi-decade tax plan.
What's Included
Roth Strategy, Modeled Annually.
- Annual conversion-window analysis
- Multi-year tax-bracket modeling
- IRMAA threshold coordination
- RMD trajectory and lifetime tax projection
- Spousal coordination for couples
- Social Security timing integration
- Estate-aware conversion strategy
- Annual review and conversion-size recalibration
The Coordination Advantage
A Roth Conversion Touches Every Tax Lever You Have.
The conversion decision is rarely just about Roth. It interacts with your tax bracket, your Medicare premium, and your future RMD picture. Here's how it all connects when one team handles all of it.
A Roth conversion is a tax decision dressed up as an investment move. The size of the conversion, the year you do it, and the bracket it fills are all tax questions answered alongside your annual tax plan. Our CPAs run the conversion modeling as part of the year-round tax strategy.
Tax Planning
A Roth conversion done in the wrong year can push you across an IRMAA threshold and add thousands to your Medicare premium two years later. The brackets are cliffs. A conversion plan that ignores IRMAA can cost more than it saves. We coordinate both before any conversion happens.
Medicare Planning
The whole point of doing Roth conversions in your 60s is usually to solve an RMD problem in your 70s. The amount you convert during the window directly reduces the size of your future RMDs and the taxes they'll generate. Conversion strategy and RMD planning are two sides of the same decision.
RMD Planning
Why Choose Leonard Financial Solutions?
Roth conversion modeling shows up at a lot of firms. Here's what makes this one different.
Fiduciary by Law
As a fiduciary firm, our advisory recommendations are legally required to be in your best interest. The conversion strategy we recommend is the one we believe fits your situation, not the one that maximizes a fee or a product sale.
Modeled Year by Year
Roth conversion decisions don't survive contact with shortcut rules. Your specific situation, your bracket, your IRMAA exposure, your projected RMDs, and your spouse's picture all matter. We model annually, not by formula, so the conversion plan adapts as your circumstances change.
Coordinated With Everything Else
Most firms either do Roth conversions in isolation or don't do them at all. We run conversion strategy alongside your tax plan, your Medicare premium, your Social Security claiming decision, and your investment portfolio. One team. One coordinated plan. One direction.
Your Retirement Coordination Review: Three Simple Steps
A coordinated conversion plan starts with one conversation. Here's how it works.
Book Your Review
Choose a time on Jonathan's calendar. Two minutes, no prep work required.
We Map Your Conversion Window
Jonathan walks through your current account balances, your projected RMDs, your tax bracket, and your IRMAA exposure. Then we sketch what a multi-year conversion plan might look like for your situation.
You Get a Clear Picture
No product pitch. Just an honest read on whether Roth conversions make sense for you, how much might be worth converting, and over how many years. Just the information you need to decide what to do next.
No cost. No obligation. Just the information you need to decide what to do next.
Common Questions Answered
Got a question? Here's where most people start.
Should I do a Roth conversion?
The answer depends on your current tax bracket, your projected income in retirement, your IRMAA exposure, your projected RMDs, and how large your traditional IRA is relative to your Roth. The conversion window is usually most valuable in the years between retirement and age 73, when RMDs haven't started yet and your income is temporarily lower. We model this every year for every client. There's no universal right amount.
How much should I convert in a single year?
There's no fixed answer, but the most common approach is to convert enough to fill up a specific tax bracket without crossing into the next one, while staying clear of the next IRMAA threshold. The exact number depends on your current ordinary income, any capital gains you've recognized, your spouse's situation, and what you want to leave to heirs. Some years it's $40,000. Some years it's $0. We size it annually based on your actual picture, not a rule of thumb.
What if tax rates go down after I convert?
Possible, but the planning case for Roth conversions usually rests on more than just future federal rates. It also rests on the math of RMDs (your traditional IRA is forced into income eventually, often at a higher bracket than you're in today), the IRMAA cliff structure on Medicare premiums, the tax treatment of an inherited IRA for non-spouse heirs (the 10-year forced drawdown rule), and the value of having a tax-free pool of assets for flexibility in your highest-spending retirement years. Rates going down is one variable. It's rarely the deciding one.
Take the Next Step
Start Building Conversion Plan
Whether you're staring at a large traditional IRA, an upcoming retirement date, or a window you've been meaning to use, the right time to model the conversion is before the year runs out. The Retirement Coordination Review is where we start. One session, your situation, no obligation.
