Start here
The Roth isn't a tax break. It's a steering wheel.
See how qualified Roth withdrawals add choices to your retirement paycheck.
Read the explanation →The Roth planning library · Rich LoPresti, CFP®, CWS®
Pay taxes on your terms.
You built the savings. Now decide how those dollars could work for you—and what the tax bill might look like when you use them.
A Roth conversion brings tax forward. Whether that is worthwhile depends on what you pay now, what you might pay later, where the tax money comes from, and the flexibility you gain. Start with the question closest to your life.
Start with the steering wheel →Not sure where to start?
Is a Roth conversion worth a look for you?
Eight questions, two minutes, nothing saved. An honest read, and the two articles to read next.
Take the check →Still working
If you believe in the Roth, why are you still feeding the IRA?
Review new contributions alongside the balance you may want to convert later.
Read the explanation →Retiring soon
The best years to convert are the ones right after the paychecks stop.
Coordinate the years between paychecks, Social Security and required withdrawals.
Read the explanation →Making the decision
Three reasons people put off Roth conversions, and the honest answer to each.
Work through cash reserves, five-year clocks and the conversation with your accountant.
Read the explanation →Required withdrawals
The freight train: what required withdrawals look like when the IRA keeps growing.
Read the explanation →Protecting your family
One of you will file alone. The tax code will notice.
Understand the change from joint to single tax brackets and what it may mean.
Read the explanation →Building your retirement paycheck
One fund got you here. Spending it takes a plan.
Respect the saving strategy that worked—and review the control you need for spending.
Read the explanation →A planning story
Two brackets, one pile of cash: how a couple chose their conversion size.
Read the story →Connecticut
How Connecticut changes the Roth conversion calculation.
Check the retirement-income phaseout alongside federal tax, healthcare costs and cash reserves.
Explore the Connecticut angle →See your dates
Map your conversion window.
The years between your last paycheck and your first required withdrawal, and what claiming later does to them.
Open the tool →The decision—not a sales pitch
Tax-free is powerful. Getting there has a price.
A Roth conversion is no silver bullet and no free lunch. You pay tax on the taxable amount now for the possibility of more flexibility and qualified tax-free withdrawals later. The right question is not “Is a Roth good?” It is “Is the price of moving these dollars into a Roth worth it for my household?”
The case for converting
A temporarily lower tax rate, money available to cover the bill, room to leave the Roth invested, fewer future pretax withdrawals, or more flexibility for a survivor and heirs can make a conversion worth analyzing.
The case against—or not yet
A higher rate today than you expect later, a cash reserve you need for living, lost health-insurance assistance, extra Medicare premiums, or an IRA intended for charity can weaken or reverse the case. Keeping the money pre-tax can be a sound decision.
The middle ground
You do not have to convert everything—or anything this year. Compare no conversion with a smaller amount, a later year and a multi-year approach. A tax-bracket ceiling is a reference point, not a command.
Look at it from these angles.
1. Tax rate now versus later
Compare the tax on the next dollars converted with the tax those dollars might face when withdrawn—not just your average tax rate. Include state taxes, a possible move and the survivor’s filing status. Under equal-resource assumptions and the same tax rates and growth, tax-free compounding alone is not a free advantage; the tax paid upfront matters.
Try the equal-resource illustration →2. Cash and the cost of paying the tax
Cash used for conversion tax cannot also pay the grocery bill or remain invested elsewhere. Selling investments may create gains; taking additional IRA money may add tax and, when applicable, penalties. Preserve a workable spending and emergency reserve.
Examine the funding choices →3. Healthcare and income thresholds
Conversion income can affect Marketplace assistance, Medicare premiums, taxation of Social Security and income-based tax benefits. Calculate the whole incremental cost, not only the federal bracket. A year before Medicare is not automatically a low-cost conversion year.
See what changes the window →4. Time, access and investment risk
How long can the money stay invested? Will you need it soon? Roth IRA qualification, distribution ordering and separate conversion clocks matter. Moving investments into a Roth does not remove market risk or make an aggressive allocation appropriate.
Connect account choices with spending and investments →5. Your spouse, heirs and charitable plans
A survivor may face different tax brackets, and beneficiaries have their own withdrawal rules and rates. Tax-exempt charities can often receive pretax IRA dollars without income tax, so paying conversion tax on that intended gift may add cost without the benefit you expect.
Look at the survivor’s picture →6. The account rules and the actual taxable amount
After-tax IRA basis, employer-plan restrictions, early-withdrawal exceptions and required minimum distributions can change the mechanics. An RMD itself cannot be converted. Once it is satisfied, other eligible dollars may still be converted; reaching RMD age is not an automatic “no.”
Understand what the Roth changes →What should you leave knowing?
Which facts strengthen your case, which facts weaken it, and which numbers could change the answer. The two-minute check gives you a starting read and two articles matched to your answers. The calendar shows timing. Neither calculates a personalized conversion amount or proves that you will save tax.
Before acting, compare the money available for spending and heirs after all taxes and costs under no conversion, a smaller conversion and a larger one. Revisit the decision as income, spending and tax rules change.
Questions across the table
Start with the decision, not the jargon.
How big will my required withdrawals get?
Required minimum distributions start at 73, or 75 for those born in 1960 or later, and equal the prior year-end balance divided by an IRS factor that shrinks each year, so the required share rises from about 4% at 75 to about 8% at 90. If the account keeps growing, the dollar amount grows too. In a hypothetical example, $1 million at age 60 growing at a constant 7% produces a first required withdrawal of about $112,000 at 75 and about $263,000 at 90; at 10%, about $170,000 and $603,000. A surviving spouse filing single pays more tax on the same withdrawal. Hypothetical illustration, not a projection. See: The freight train.
The freight train →How does Connecticut tax a Roth conversion?
Federal AGI can reduce the state subtraction for eligible retirement income. Compare the full household cost rather than automatically avoiding the phaseout band.
See the Connecticut explanation →Which bracket should I fill, 22% or 24%?
Read the story →How much should I convert?
Compare several amounts—including no conversion. A bracket boundary is one reference point, not an automatic target. Cash reserves, Medicare or Marketplace costs, state taxes and future withdrawals can change the answer.
See how to size the window →Where does the money for the tax come from?
Start with what your cash already needs to cover. Selling investments can create gains; extra IRA withdrawals can add more tax. A smaller conversion can be the better choice if paying the bill would squeeze your reserves.
Compare tax-funding choices →Should I wait until I retire?
A full year without wages may open room, but pensions, Social Security and healthcare costs matter. While working, review contribution choices and whether a smaller conversion fits.
Explore the working-years choices →Does converting guarantee that I pay less tax?
No. Paying tax sooner can help in some circumstances and hurt in others. Compare the after-tax money available to your household, not just the size of an account or one year’s tax bill.
Understand what the Roth can and cannot do →What changes when one spouse is left?
Filing status, income and benefit rules can change together. Planning ahead can give the survivor more choices about taxable withdrawals.
Explore the survivor’s tax picture →See where you stand.
Start with where you stand: what you own, and where you hold it.
Open Your Retirement Snapshot →Explore the numbers.
Adjust educational illustrations of spending, compounding and future tax effects.
Visit the decision lab →Connect it to your life.
A complimentary discovery conversation starts with your situation and whether further planning together fits.
Talk with Rich →Educational content, reviewed October 9, 2026. These explanations are not individualized recommendations or guarantees of tax savings. Qualified Roth distributions and conversions have specific tax rules. See all resources · Explore hypothetical planning stories