Retirement Tax Planning
Taxes, not investments, determine how long your retirement lasts.
The biggest variable in retirement isn't market returns. It's taxes. Most retirement plans model your investments and call it done. We start with your lifetime tax bill instead, because the decisions you make about withdrawals, conversions, and timing shape how long your money actually lasts far more than an extra percent of portfolio return ever will.
Who This Is For
You've Saved Diligently. Now Someone Needs to Plan the Tax Side.
This page is built for pre-retirees and retirees with $1 million or more saved in pre-tax 401(k)s and IRAs who are within about ten years of retirement, or already retired, and have never had anyone show them what those savings will actually cost at tax time.
You and your spouse have $1 million or more saved in pre-tax 401(k)s and IRAs, built through years of consistent saving, and you're within about ten years of retirement or already there.
No one has ever sat down with you and shown what your pre-tax savings actually cost once required withdrawals, Social Security, and Medicare premiums all show up on the same tax return.
You're aware of required minimum distributions, Social Security taxation, IRMAA surcharges, and the widow's penalty in the abstract, but nobody has modeled how they apply to your specific numbers.
Your current advisor talks with you about asset allocation and market performance. Very few sit down and walk through the tax bill that's been building since your first payroll deduction.
If that sounds like your situation, you're exactly who we built the Retire Ready Roadmap™ for.
How It Works
A Tax-First Plan, Built Around Your Numbers
Here is the short version of how a tax-first retirement plan comes together. For the full step-by-step timeline, including what to expect at each visit, see How We Work.
Step 01 · One-Time
We Build Your Retire Ready Roadmap™
We model your lifetime tax trajectory, not just next year's return: Roth conversions, withdrawal sequencing, Social Security timing, healthcare costs, and legacy, all mapped out together instead of decided one piece at a time.
Step 02 · Ongoing · Optional
We Coordinate Every Piece
Roth conversions, withdrawal sequencing, Social Security timing, healthcare costs, and legacy planning are connected decisions. We coordinate them together so a choice made in one area doesn't create an avoidable tax cost in another.
Step 03 · Ongoing
We Monitor and Adjust
Tax laws change. Markets move. Your life changes. We revisit your plan regularly to keep your tax strategy aligned with what's actually happening, not what we assumed when we built it.
The Bigger Lever
Why Taxes Are the Biggest Retirement Variable
Most retirement conversations focus on investment returns: what should be in stocks, what should be in bonds, how much risk is too much. Returns matter, but they typically vary by a few percentage points a year, and no one, including us, can control them.
Tax decisions are different. The choice of when to convert to Roth, in what order to draw from which accounts, and when to start Social Security can swing your after-tax income by tens of thousands of dollars a year, and those decisions are largely within your control.
A plan that focuses almost entirely on the variable you can't control, market returns, while ignoring the variable you can control, your tax strategy, is missing the bigger opportunity. Retirement tax planning starts by flipping that order: taxes first, then the investment strategy built to support it.
Forced Withdrawals
RMDs: Forced Income You Didn't Plan For
Once you reach age 73, or 75 depending on your birth year, the IRS requires you to start withdrawing a minimum amount from your pre-tax 401(k)s and IRAs every year, whether you need the money or not.
These required minimum distributions count as ordinary taxable income. On a large pre-tax balance, they can be substantial, and they can push you into a higher tax bracket than you expected, increase how much of your Social Security is taxed, and trigger IRMAA surcharges on your Medicare premiums, all in the same tax year.
Because RMDs are calculated off your account balance, the size of the eventual bill is largely determined by decisions made years earlier: how much you converted to Roth, how you sequenced withdrawals, and how proactively you planned before the RMDs became mandatory. By the time RMDs start, most of the planning window to reduce them has already closed.
Social Security
Social Security Taxation and Provisional Income
Many retirees are surprised to learn that Social Security benefits can themselves be taxed. Depending on your provisional income, a combination of your adjusted gross income, tax-exempt interest, and half your Social Security benefit, up to 85% of your benefit can be included in your taxable income.
For 401(k) and IRA millionaires, this usually isn't a fringe scenario. Once RMDs and other retirement income are added in, most households land in the range where a large share of Social Security is taxable by default.
Roth conversions completed before Social Security and RMDs begin, along with thoughtful withdrawal sequencing once you're retired, can reduce your provisional income and lower how much of your Social Security benefit ends up taxed. It's one of the more overlooked levers in a retirement tax plan, because Social Security itself often isn't the first thing people think to plan around.
Medicare Costs
IRMAA: The Hidden Medicare Tax
IRMAA, the Income-Related Monthly Adjustment Amount, is a surcharge Medicare adds to Part B and Part D premiums for higher earners. It's based on your modified adjusted gross income from two years prior, so a high-income year today can mean higher Medicare premiums two years from now.
The IRMAA brackets have historically not kept pace with inflation, which means income levels that once felt comfortably below the thresholds can drift into surcharge territory as RMDs grow. A single large withdrawal, a big Roth conversion, or a lump-sum event can be enough to trigger a jump.
Because IRMAA is based on income you control, at least in part, planning ahead matters. Spreading conversions across multiple years, sequencing withdrawals deliberately, and watching your modified AGI in the years that count can keep your Medicare premiums closer to the baseline instead of the surcharge tier.
Account Types
Tax Diversification: Not All Accounts Are Equal
Pre-tax accounts (traditional 401(k)s and IRAs), Roth accounts, and taxable brokerage accounts are taxed differently in retirement, and that difference is a planning tool, not just an accounting detail.
Withdrawals from pre-tax accounts are taxed as ordinary income. Qualified withdrawals from Roth accounts are tax free. Withdrawals from taxable accounts may trigger capital gains tax, but often at a lower rate, and only on the growth, not the full withdrawal.
Having meaningful balances across all three account types gives you control over your taxable income in any given year. In a year when you need extra cash for a large purchase, you can draw from the account that costs you the least in tax, rather than being forced into whichever account happens to hold the money. Most 401(k) and IRA millionaires are heavily concentrated in the pre-tax bucket, which is exactly the imbalance a tax-first retirement plan is built to correct.
Common Questions
Retirement Tax Planning FAQ
Straight answers to the questions we hear most about RMDs, Social Security taxation, and IRMAA.
Retirement tax planning is the process of managing your lifetime tax bill across retirement, rather than just filing an accurate return each year. It covers Roth conversions, withdrawal sequencing, Social Security timing, RMD management, and IRMAA exposure, coordinated together instead of decided separately.
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Areas We Serve
Serving Clients Nationwide, With Local Expertise Across Kansas City
We build tax-first retirement plans for 401(k) and IRA millionaires across the country. We also happen to be based in Overland Park, Kansas, with deep roots in Johnson County communities including Olathe, Lenexa, Leawood, Prairie Village, Shawnee, and Mission. If you're local to the Kansas City metro, find your community below.