Retirement Tax Optimizer — Free Roth Conversion & Withdrawal Strategy Calculator
Americans overpay an average of $6,000–$12,000/year in retirement taxes they didn’t have to pay. Find the specific strategies — Roth conversion timing, Social Security tax optimization, withdrawal sequencing, RMD planning — that apply to your retirement accounts, age, and state.
✓Free. 11 questions. 3 minutes. Email only to unlock your playbook.
How do I optimize taxes in retirement?
Five strategies reliably reduce retirement taxes for most Americans: (1) Roth conversions in low-income years before RMDs start at age 73, (2) tax-efficient withdrawal sequencing (taxable accounts first, Roth last), (3) state residency planning (0% vs. up to 13.3% income tax), (4) Qualified Charitable Distributions after 70½, and (5) IRMAA bracket management to avoid Medicare surcharges. Frank Finly’s tax optimizer identifies the ones that fit your situation, ranked by estimated annual savings.
If any of this feels familiar, you’re leaving money on the table.
The tax drag you can feel but can’t name.
“I’m getting hit from every direction.”
Pension, Social Security, rental income, RMDs, dividends, maybe a part-time job. Each one changes your bracket. You can’t tell which lever to pull.
“Does Roth conversion apply to me?”
Generic articles say “Roth conversions save taxes.” Okay. How much? In which year? Before or after Social Security? For you, in your state, at your income — that’s the real question.
“Nobody tells me what I should’ve done.”
TurboTax and CPAs are backward-looking. They clean up the past. They don’t optimize the future.
Why tax planning feels impossible — and how we fix it
Two problems stop smart people from optimizing taxes. We solve both.
- •The jargon wall — Roth, pro-rata, IRMAA, NIIT — the acronyms alone make brains shut down. We translate every strategy into one number: “convert $X this year, save $Y across 10 years.”
- •The timing trade-off — Most advice asks you to sacrifice today for abstract gains decades out. We lead with strategies that save you money this year — present-you and future-you on the same team.
Personalized strategies. Honest ranges. Real trade-offs.
What makes this different from every “10 tax tips” article.
Personalized Strategies
Not generic tips — real strategies matched to your retirement accounts, age, and timeline.
Roth Conversion Window
The years before RMDs start are your golden window — see if you’re using it.
Avoid Tax Surprises
Social Security taxation, IRMAA surcharges, RMD bracket spikes — see what’s coming.
Dollar Amounts
Every strategy shows estimated annual savings in real dollars (as a range, not a false-precision single number).
What the dashboard actually gives you
- →Retirement tax rate projection — current trajectory vs optimized, including RMD impact
- →Top 3 strategies ranked by estimated $-savings with confidence indicators
- →Full playbook of all applicable retirement tax strategies
- →Decision branches where two strategies conflict (Roth aggressive vs gradual, SS early vs delay)
- →Golden window analysis — years between retirement and RMDs mapped to Roth conversion opportunity
How it works
Answer 11 quick questions
Retirement accounts, pre-tax/Roth balance, Social Security plans, retirement status, filing status, state, age. 3 minutes.
See your retirement tax picture
Projected retirement tax rate (current trajectory vs optimized). Top 3 strategies ranked by estimated annual savings.
Decide or delegate
Each strategy includes how-to guidance. DIY, or connect with an advisor who specializes in your situation.
Here’s what you’ll see
Effective rate: 28%
$23,500 paid in federal + state last year. Here’s how to lower it.
Roth conversion: $4K–$8K/yr
Convert in low-income years before RMDs. Clear win for most pre-retirees.
CA→FL: $6K–12K/yr
Relocation analysis includes break-even on moving costs.
Decision branches
“Roth now vs. later” shown side-by-side. You decide.
Sample based on a 62-year-old with $800K Traditional IRA, $40K pension, SS at 67, CA resident. Your situation will produce your own playbook.
What changes after 3 minutes
Why trust our analysis
15+ years of retirement & tax planning expertise
Built by professionals who’ve navigated hundreds of multi-income-source retirees through Roth conversions, RMD strategies, and state relocations.
IRS-accurate calculations
Federal tax brackets, state rates, FICA, Medicare surtax, NIIT, IRMAA. All the hidden taxes, modeled.
Ranges, not false precision
Tax optimization depends on future variables. We show honest ranges and flag uncertainty.
All income sources in one model
Pension + SS + rental + RMD + dividends + part-time work — integrated. That’s where the real optimization lives.
Your data stays yours
Bank-level encryption. We never sell your data.
Expert insights
Deep-dive articles from our tax planning team.
Roth Conversion Timing for 2026
When to convert — and when to wait. The decision framework for this year.
RMD Calculator: Calculate Your Required Minimum Distributions
Understand your required withdrawals and plan your tax strategy.
State Tax in Retirement: Where to Live
How CA, NY, IL retirees actually save by relocating — and when the math breaks down.
Retirement Tax Traps — and How to Defuse Them
Why your Traditional IRA is a time-bomb at 73 — and the 10-year window to fix it.
Frequently asked questions
How to convert a Traditional IRA to a Roth without paying taxes?+
The short answer: you can’t do it completely tax-free, but you can minimize the bill. Three main strategies: (1) convert in low-income years — gap years between retirement and age 73 when RMDs start, (2) convert amounts that stay within your current bracket, and (3) use the pro-rata rule awareness if you have after-tax contributions. For most pre-retirees, the “Roth conversion window” between retirement and age 73 is worth $50K–$200K+ in lifetime tax savings.
What is a Roth conversion, and when does it make sense?+
A Roth conversion moves money from a pre-tax account (Traditional IRA or 401(k)) to a Roth account. You pay income tax on the converted amount now, in exchange for tax-free growth and withdrawals later. It makes sense when your current tax bracket is lower than your expected retirement bracket, when you have a large Traditional IRA at risk of the “RMD tax bomb” at 73, or when you want tax diversification in retirement.
What is the pro-rata rule, and how does it affect me?+
The pro-rata rule says that if you have both pre-tax and after-tax money in your Traditional IRAs, any conversion is proportionally treated as pre-tax and after-tax. This complicates the “backdoor Roth” strategy for high earners. If you have no after-tax Traditional IRA money, pro-rata doesn’t affect you. The optimizer flags this based on your account types.
How do I avoid IRMAA Medicare surcharges?+
IRMAA adds up to $5,000+/year in Medicare Part B & D premiums once your income crosses thresholds (~$103K single / $206K married in 2026). Keep your MAGI below the threshold in years you’ll be on Medicare (65+). Key tactics: spread Roth conversions across multiple years, use QCDs after 70½ to reduce AGI, harvest gains strategically.
Is this really free?+
Yes. The tax optimizer and full playbook are free. Frank Finly is paid by the advisors we match users with — you never are.
Why do you show ranges instead of exact savings numbers?+
Because tax optimization depends on future unknowns: tax law changes, your actual income, life events. We show honest ranges and flag uncertainty. Calculators that give you one exact number are either lying or ignoring reality.
How is this different from TurboTax or a CPA?+
TurboTax and CPAs are backward-looking — they handle last year’s return. The Retirement Tax Optimizer is forward-looking — it identifies retirement tax strategies to implement this year and across the Roth conversion window. Bring the playbook to your CPA; it makes the conversation 10× more productive.
Does it handle my state’s taxes?+
Yes. We model all 50 states, including the 9 states with no income tax on retirement income (FL, TX, NV, WY, SD, WA, AK, TN, NH). Relocation analysis included.
I have a Traditional IRA — is the "tax bomb" real?+
Yes. At 73, RMDs force taxable withdrawals whether you need the money or not. If your balance is large, RMDs can push you into a higher bracket and trigger IRMAA. The Roth conversion window before 73 is the key fix — the optimizer shows you if it applies and how much to convert per year.
What if the strategies conflict?+
Some will. That’s why we have decision branches — “Option A vs Option B” with the trade-offs spelled out. You decide based on your priorities, or ask an advisor.
Will you sell my data?+
No. Bank-level encryption, never sold, never shared without your permission.
Stop paying tax you don’t have to
11 questions. 3 minutes. Frank Finly’s free retirement tax optimizer — with Roth conversion, Social Security, withdrawal sequencing, and RMD strategies ranked by estimated annual savings.