Sponsored by
Hey, it’s Jeffrey — back again!
I've always been a Roth IRA person.
Not because I ran the numbers. Because it felt like everyone said it’s the best. You pay the taxes now, the money grows tax-free, and future-you doesn't owe anything. What's not to like?
I never actually checked whether that was true for my situation.
Turns out many people haven't. They often pick Roth based on the vibe — something they read once, or what their parents said, or what a friend happened to mention. But the actual math takes about five minutes with AI.
So I did it.
Here's the prompt I used:
I want to figure out whether I should be contributing to a Roth IRA or a Traditional IRA — and I've never actually run the math on my own situation.
Before we start, one important note: if you file your taxes as married filing separately, Roth IRA contributions are phased out almost entirely (the limit drops to $0 at $10,000 of income). If that's your situation, let me know and we'll talk through your alternative options instead of running this comparison.
Otherwise, here's my information:
My current situation:
Filing status: [Single / Married Filing Jointly / Head of Household]
Gross income: [$X — or household income if filing jointly]
State I live in: [State]
Current IRA type (if I have one): [Roth / Traditional / Both / None]
My age: [X]
Years until I plan to retire: [X]
My retirement income picture — help me estimate this:
I'm not sure what my retirement income will look like, so please ask me the following questions one at a time and use my answers to estimate my expected taxable income in retirement:
How much do I currently have in Traditional IRA and/or Traditional 401k accounts combined?
How much am I contributing to those accounts each year?
Do I have a pension? If so, roughly how much would it pay per month?
Have I checked my Social Security estimate at ssa.gov? If yes, what does it show for my expected monthly benefit? If not, estimate based on my income history.
Once you have those answers, please:
Estimate my likely taxable income in retirement using a 4% withdrawal rule on my traditional accounts, plus Social Security (up to 85% of which is taxable depending on income), plus any pension
Compare my current marginal tax rate to my estimated retirement marginal rate
Tell me clearly whether Roth or Traditional looks better for my situation — and if the answer is genuinely close, tell me that too and explain why a split might make sense
Flag any other factors I should know about, including income limits, the backdoor Roth option, Required Minimum Distributions (RMDs), and how my existing account mix affects the decision
Important: Please frame your output as a starting point for further research and a conversation with a financial advisor — not a final recommendation. This math is useful for understanding my situation, but the right answer depends on factors only a professional can fully assess.
Here's what came up when I ran it on my situation 👇
I used a hypothetical single-filer scenario (since I’m now married and we file separately): $130k income, Rhode Island, 20 years to retirement, existing Roth IRA and Traditional solo 401k.
My current marginal rate: 24% federal plus about 4.75% state. My estimated retirement marginal rate: 22% federal across both phases, before and after Social Security kicks in.
The math said Traditional has a slight edge. Two percent isn't dramatic, but it's real and 20 years of compounding on that deduction matters.
But the more interesting thing the AI flagged wasn't the rate comparison. It was the RMD risk: if I kept going all-in Traditional, Required Minimum Distributions starting at 73 could eventually force withdrawals that push me into a higher bracket than I'm saving at now, which would make the whole bet backfire.
The actual recommendation: contribute Traditional on the 401k side to capture the 24% deduction, but keep the Roth IRA going for tax diversification. Not all-in either direction. A split.
I went in a Roth believer. I came out with a different answer than I expected, and a clearer sense of what to actually talk through with a financial advisor.
This is exactly the kind of thing that's worth doing the math on before that conversation. Not instead of it.
One quick note: This newsletter is for educational and research purposes only and does not constitute financial advice. Tax and retirement decisions are personal and complex. Use this as a starting point, then talk to a qualified financial advisor before making any changes.
Keep going? Want to go further? Try these follow-up prompts after you get your initial result:
If your result was close: "I got a mixed result on Roth vs. Traditional. Model two scenarios for me: one where I go all-in Traditional for the next 20 years, and one where I split contributions 50/50. Show me the estimated RMD at age 73 in each scenario and what tax bracket that would put me in."
If you have a large Traditional balance: "I have $[X] in Traditional retirement accounts. Walk me through a Roth conversion strategy. How much could I convert annually in low-income years to reduce my future RMD burden without pushing myself into a higher bracket?"
If you're a high earner near the Roth income limit: "My income is near or above the Roth IRA phase-out limit. Explain how the backdoor Roth IRA works, whether I'm eligible, and what steps I'd need to take to execute one this year."
AI tip worth trying this week: Meeting records to task list
I asked Claude about something that had recently changed: a new version of a product that had launched just a few months earlier. It pushed back confidently and told me the new version didn't exist, because as far as its training data was concerned, it didn't. I knew better, pushed back, and it had to search and correct itself.
The lesson: AI models don't flag when they're out of date, so any time you're asking about something that could have changed recently, treat the answer as the start of your research, not a final word. Of course you won't always know when something's out of date, but it's a good lesson to be skeptical
The next A.I. boom could create massive winners just like the 1990s tech surge. We identified 7 small tech companies positioned to benefit from the next phase of A.I. growth. View the 7 Stocks.
One quick note: This newsletter is for educational purposes only and does not constitute financial advice. I'm not a financial advisor — just someone sharing ideas and tools I've found useful. Use what works for you, skip what doesn't, and always do your own research. Some links may be affiliate links or sponsored content for which I may receive compensation.