For many high-balance savers, the question isn’t just how much to withdraw from retirement accounts, but when and how. Converting traditional IRA funds to a Roth IRA can look attractive — no required minimum distributions (RMDs) later, tax-free growth, and more flexibility for heirs. But timing, taxes, and strategy all matter. Here are five things to consider if you’re thinking about converting a significant portion of a traditional IRA to a Roth.

Traditional IRAs are funded with pre-tax dollars, so any amount you convert counts as taxable income in the year of conversion. If you’re considering a large conversion, it could push you into a higher tax bracket and affect Medicare premiums or Social Security taxation. Use tools like theIRS Tax Withholding Estimator or a free calculator fromSmartAsset to model your potential bill.

Action Step: Run a tax projection before converting. Many online calculators can help you estimate the cost of different conversion amounts.

2. Weigh Your Current vs. Future Tax Rates

The core question: Will your tax rate now be lower than in retirement? If you’re in a historically low bracket, converting may make sense. But if your income will drop dramatically after you stop working, waiting might be wiser. Studies from Vanguard and Morningstar show that partial conversions over several years often produce better results than one big move.

Action Step: Map out your expected income and tax brackets for the next 5–10 years. A planner or CPA can help you forecast scenarios.

3. Consider the Impact on RMDs and Medicare

One reason people convert is to reduce futureRequired Minimum Distributions (RMDs) from traditional IRAs, which can trigger larger tax bills and higher Medicare Part B/D premiums. Converting now can help flatten those future distributions, but only if it doesn’t create a bigger problem in the short term.

Action Step: Use a calculator such asSchwab’s RMD estimator to see how your RMDs might change under different conversion strategies.

4. Think About Legacy and Estate Goals

Roth IRAs can be more attractive to heirs because withdrawals are tax-free (if rules are met), and they don’t carry RMDs for the original owner. Under the SECURE Act, most non-spouse beneficiaries must deplete an inherited IRA within 10 years; Roth status can make that tax-free.

Action Step: Clarify who will inherit your accounts and whether a Roth conversion aligns with your legacy plan. Tools likeFidelity’s Inherited IRA overview provide a quick explainer.

5. Explore Partial Conversions and Professional Guidance

You don’t have to convert everything at once. Many retirees do “Roth laddering,” moving manageable amounts each year to stay in a target tax bracket. This can smooth out taxes and preserve flexibility.

Action Step: Test different scenarios. Apps likeNewRetirement orRightCapital let you model conversions. And of course, a qualified financial advisor can tailor the math to your situation.

Roth conversions can be powerful, but they’re not one-size-fits-all. Taxes, income, health coverage, and legacy goals all intersect. As you plan your retirement income, consider modeling different scenarios and seeking professional advice.

At Age Brilliantly, we connect members with trusted professionals who can help run the numbers and design a strategy that fits your 100-year life plan.

What’s your biggest question about Roth conversions and long-term tax planning? Join the discussion in ourAge Brilliantly Forum to share your thoughts and learn from others.