Tax Planning
Fiduciary Wealth Management
The Largest Expense Nobody Plans For.
For most retirees, taxes are the single largest expense across the rest of their lives. Larger than housing. Larger than healthcare. Larger than the cost of every vacation, every gift to the grandkids, and every replacement roof combined. And yet for most households, tax planning happens once a year, in April, after every decision that mattered has already been made. By then the only question left is how much you owe.
We run tax planning year-round, integrated directly into your investment, income, and retirement decisions. Our in-house CPAs model the tax impact of every move before you make it: Roth conversions, withdrawal sequencing, capital gains, IRMAA thresholds, charitable giving, RMD timing. The work is proactive, coordinated, and continuous. The goal isn't to pay less tax this year. It's to pay less tax over the rest of your lifetime.
WHO THIS IS FOR
Built for Retirees With Multiple Tax Levers.
Clients with $500K to $5M in retirement assets, particularly those with a mix of traditional IRA, Roth, and taxable accounts. If you have a large traditional IRA building toward RMDs, ongoing capital gains from a taxable portfolio, Social Security on the horizon, and no coordinated tax plan tying it all together, this is the conversation to have. Especially valuable in the years between retirement and age 73, when the tax planning window is widest.
Pillars of Your Tax Strategy
Year-round tax planning isn't one decision. It's a series of timing calls made across investments, income, and life events. Here's how we handle each one.
Year-Round Bracket Management
Most retirees only think about their tax bracket once, when they file. Our CPAs track your projected bracket throughout the year and look for opportunities to fill the lower brackets efficiently. Realizing a long-term capital gain into the 0% bracket when it's available. Recognizing income in a year when you're already in a low bracket because you haven't started Social Security yet. Timing the larger withdrawals into the years where they cost the least. Bracket management is small decisions made consistently, not heroic moves made annually.
Roth Conversion Modeling
The years between retirement and age 73 are where Roth conversion strategy moves the most money. Convert too little and you leave a traditional IRA building toward an RMD problem and the higher tax brackets that come with it. Convert too much and you push yourself into a higher bracket today, or trigger an IRMAA surcharge two years from now. We model the conversion window every year, against your projected income, your projected RMDs, your spouse's situation, and your estate goals. There's no universal right amount. There's a right amount for this year.
Coordinated Withdrawal & Asset Location
Which account you draw from changes your tax bill. What you hold in each account changes your tax bill for the next twenty years. Tax-efficient investments belong in your taxable accounts. Tax-inefficient ones belong in your IRAs. Roth assets should generally grow untouched. These are simple rules in theory and almost never followed in practice, because most portfolios were built one account at a time, in different places, by different people. We coordinate asset location across every account in one plan.
Let's Build Your Tax Plan
On your Chain Reaction Audit, Jonathan reviews your current tax exposure, your projected RMD trajectory, and your Roth conversion window. Then we show you how tax planning can be coordinated with the rest of your retirement plan. No pressure. No product pitch. Just clarity.
Layer 01
Year-Round Strategy
Tax planning that runs continuously, not annually. Bracket management, conversion timing, capital gains harvesting, and income smoothing handled in real time, integrated with the investment decisions that drive them.
Layer 02
Multi-Year Modeling
The decisions that matter most in retirement tax planning rarely pay off in the same year you make them. Roth conversions affect RMDs ten years out. IRMAA brackets reflect income from two years prior. We model your tax picture across the next ten to fifteen years, not just the current return.
Two layers. One coordinated tax strategy. The kind of work most CPAs don't do because they're scoped to file the return, not plan the decade.
What's Included
Tax Planning, Year-Round.
- Annual Roth conversion modeling across multi-year horizon
- Projected RMD planning and tax-impact analysis
- Bracket management and income-timing strategy
- Capital gains harvesting (and loss harvesting)
- Asset location coordination across all accounts
- IRMAA bracket monitoring and conversion timing
- Qualified Charitable Distribution (QCD) strategy at 70½
- Annual tax return preparation through our CPAs
The Coordination Advantage
Tax Decisions Touch Everything.
Almost every retirement decision has a tax consequence. Here's how tax planning connects to the rest of your plan when one team handles all of it.
A Roth conversion is a tax decision dressed up as an investment move. How much you convert, in which year, depends entirely on your current bracket, your projected RMDs, and your IRMAA exposure. Our tax planning and Roth conversion strategy are run as one decision, not two.
Roth Conversions
Required Minimum Distributions at age 73 are the single largest forced taxable event most retirees face. The size of your RMD is set by the size of your traditional IRA at age 72. Tax planning in the years before 73 is mostly about managing that future tax event before it arrives.
RMD Planning
IRMAA is a tax surcharge on your Medicare premium, triggered by your income from two years ago. Every tax decision you make today affects what you pay for Medicare two years from now. We model both together so a tax-smart Roth conversion doesn't quietly become a Medicare bill.
Medicare Planning
Why Choose Leonard Financial Solutions?
There are a lot of CPAs available. Here's what makes this one different.
Fiduciary by Law
As a fiduciary Registered Investment Advisor, our advisory recommendations are legally required to be in your best interest. That standard extends to the tax decisions we coordinate alongside your investment plan.
Our CPAs, Year-Round
Tax planning at LFS is handled by our CPAs, not a once-a-year preparer. They run the numbers before the decisions get made, not after. You meet the same team on day one and work with them every year.
Coordinated With Everything Else
Most CPAs prepare returns. Some do tax planning. Almost none coordinate that planning with your investment portfolio, your Medicare premium, your Social Security timing, and your estate plan in the same room. We do.
Your Chain Reaction Audit: Three Simple Steps
A coordinated tax plan starts with one conversation. Here's how it works.
Book Your Audit
Choose a time on Jonathan's calendar. Two minutes, no prep work required.
We Map Your Income Sources
Jonathan walks through your current bracket, your projected RMDs, your Roth conversion window, and your IRMAA exposure. When the technical tax detail calls for it, our CPAs join to model the numbers.
You Get a Clear Picture
No product pitch. Just an honest read on whether your current tax strategy is working, where the gaps are, and what a coordinated plan would look like for your situation.
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?
Possibly. 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 and your income is temporarily lower. We model this every year for every client. There's no universal right amount.
How is this different from my current CPA?
Most CPAs are scoped to prepare returns. They look backward at the year that just ended and tell you what you owe. Our CPAs work alongside the investment and retirement plan year-round, modeling the tax impact of decisions before they happen: a portfolio rebalance, a Roth conversion, a withdrawal sequence, a charitable gift. The goal is to lower your lifetime tax bill, not just file an accurate return.
What's IRMAA and why does it matter for tax planning?
IRMAA is the Income-Related Monthly Adjustment Amount, a surcharge added to your Medicare Part B and Part D premiums when your income crosses certain thresholds. The thresholds are cliffs (one dollar over and you pay the full surcharge) and they're based on your tax return from two years ago. That means a Roth conversion done in 2026 affects your Medicare premium in 2028. Tax planning that ignores IRMAA can cost more than it saves.
Take the Next Step
Start Building Your Tax Plan
Whether you're looking at a large IRA balance, an upcoming RMD, or a Roth conversion decision you've been putting off, the right time to plan is before the decision is made. The Chain Reaction Audit is where we start. One session, your situation, no obligation.
