Tax Planning for Retirees in Boston, MA — Roth Conversions, RMDs, and Lifetime Tax Strategy

Why retirement tax planning matters

For most of your working life, tax planning is a once-a-year exercise: gather documents, file the return, hope for a refund. Retirement changes the math entirely. You now have a 20- to 30-year planning horizon where the order you withdraw from accounts, when you convert pre-tax money to Roth, when you take Social Security, and when you trigger Medicare premiums all interact in ways that can swing your lifetime tax bill by hundreds of thousands of dollars.

Most retirees pay more lifetime tax than they need to. Not because the strategies are exotic, but because most advisors do not model multi-year scenarios. They focus on this year’s return. We focus on the next 30 years.

Roth conversions in retirement

The years between when employment income ends and when Social Security and Required Minimum Distributions begin — what we call the “tax gap years” — are often the most strategically important window of a retirement. In those years, your taxable income may be unusually low, leaving room in lower tax brackets to convert pre-tax IRA money to Roth at a fraction of what the conversion would cost later.

A successful Roth conversion strategy is not a single decision — it is modeled across multiple years using Holistiplan, accounting for Social Security claiming age, RMD start date, IRMAA brackets, and projected long-term tax rates. We do not just ask “should I convert?” — we model how much, what year, and from which account.

For a deeper walkthrough, see Roth Conversions in 2025: A Window Retirees Shouldn’t Ignore and Roth IRA Conversions in Retirement: What to Know Before You Decide.

Tax-efficient withdrawal sequencing

Once you are drawing income from your portfolio, the question becomes: which accounts first? The conventional answer (“taxable, then tax-deferred, then Roth”) is a starting point, not a strategy. Real-world sequencing depends on your bracket each year, the size of each account, your projected RMDs, and whether you are trying to leave Roth assets to heirs.

We model withdrawal sequencing year-by-year, looking for opportunities to harvest capital gains in low-bracket years, do partial Roth conversions when bracket space allows, and avoid pushing into the next IRMAA tier or losing tax credits at the margin.

For specifics, see Tax-Efficient Withdrawals — Keeping More of Your Retirement Income.

Required minimum distributions (RMDs)

Starting at age 73 (or 75 if you were born in 1960 or later, per the SECURE 2.0 Act), you are required to take a minimum distribution from your pre-tax retirement accounts each year. Miss it and the penalty is significant.

But the smarter question is not “how do I take my RMD?” — it is “how do I reduce my lifetime RMDs?” Roth conversions in your 60s, qualified charitable distributions starting at 70½, and Roth-friendly account allocation all reduce the size of the RMDs you will be forced to take in your 70s and 80s.

For a deeper look, see RMDs Explained — When They Start and How to Reduce Them.

Charitable giving strategies

For retirees who give to charity, the right vehicle matters. The two highest-leverage strategies for most retirees:

Qualified Charitable Distributions (QCDs) — once you turn 70½, you can donate directly from an IRA to a qualified charity (currently up to $105,000 per year, indexed). The distribution counts toward your RMD but does not show up as taxable income. For retirees who do not itemize, this is essentially the only way to get a tax benefit from charitable giving.

Donor-Advised Funds (DAFs) for bunching — if you have a high-income year (say, a Roth conversion year), you can front-load several years of charitable giving into a DAF to itemize that year, then take the standard deduction in subsequent years. We model this against your overall tax picture.

For more on tax-aware giving, including changes under recent legislation, see Smarter Charitable Giving Under the Big Beautiful Bill.