Can AI Build Your Retirement Plan?
on Sep 25, 2026
ChatGPT, Claude, and the new AI retirement apps are a great place to start. They can explain the concepts and run rough numbers. What they can’t do is see your whole picture or stand behind the answer.
Lately I have some version of this conversation every week, and so does everyone on our team. A client emails over a long list of questions, and it turns out they asked ChatGPT or Claude what they should ask their planner. Or someone comes to our first call having already run their retirement through an AI tool, and they want to know if it’s right.
I love that people are doing this. We use AI at MainStreet too, and it’s a smart way to get started. Ask it to explain a Roth conversion, or RMDs, or why Medicare premiums go up with income, and you’ll walk into your next planning meeting sharper. Often it lands on the same general direction we’d give. Where it gets into trouble is the moment a general answer meets your specific numbers.
Walk through it with me. The standard advice on Roth conversions is to convert in your low-income years, after you stop working and before required withdrawals begin, and for a lot of people that’s exactly right. I wrote about that window in Is There Room Left in Your Tax Bracket? This year we worked with a client who had roughly $3 million in a 401(k). When we modeled his actual accounts, conversions barely dented his future required withdrawals, and the extra income would have raised his Medicare premiums through IRMAA, the surcharge Medicare sets using your tax return from two years earlier. For him, the popular move was the expensive one. An AI answer to “should I do Roth conversions?” would have said yes.
That’s true of every AI tool, whether it’s a chatbot like ChatGPT, Claude, Gemini, or Copilot, or one of the retirement apps with AI built in. The apps are a step up, since they’re built for the job and ask for real numbers, but all of them work only from what you type in. None of them knows about the pension election deadline, the beneficiary form that doesn’t match your new trust, or the roof you’re replacing next year. They can also be wrong with total confidence. Kassy, who talks with most of our prospects, likes to tell them we hallucinate less, and she’s only half joking. The most important question you’ll ask, can I stop working, deserves better than a guess that sounds sure of itself.
Kiplinger tested this over the summer, putting ChatGPT, Gemini, and Claude through real retirement questions alongside answers from CFP® professionals. The bots got the math right and missed the person. As one planner in that piece put it, AI “only answers the question that you ask. It’s not asking for additional information or asking for clarification.” Asking those questions is the whole point of discovery.
It also deserves someone who answers for it. As a CFP® professional, I’m required by CFP Board to act as a fiduciary, in your best interest, whenever I give you financial advice. We’re fee-only, so we don’t sell products, we don’t manage your investments, and nobody here earns more because of what you decide. An app can’t make that promise, because nobody is on the other end of it.
So, here’s what I’d ask. Use ChatGPT, Claude, or whatever tool you like to get started, and bring us your questions. Please don’t bring the whole AI-generated plan, because we won’t review it. It isn’t that we’re ignoring your work. We can’t stand behind a plan built on inputs we haven’t seen, so we build yours from the ground up, the same way every time, following the seven steps CFP Board lays out for financial planning.
It starts with discovery, where we get to know your full picture and your goals, with your statements, tax returns, benefits, a cash flow worksheet, and a financial survey where every question is there for a reason. Then comes analysis, where we model your current path and the alternatives, stress-test them against lower returns and a market drop right at retirement and run the tax side year by year. That’s the step where the $3 million 401(k) problem showed up. From there we develop the recommendations, walk you through them, help you put them in place in your own accounts, and keep checking in as your life and the tax rules change.
If you’re a client and you’ve been saving up AI questions, send them our way before your next meeting. We’d much rather talk through what’s on your mind than have you wonder. And if you’re getting close to retirement and doing your homework, AI is a fine place to start. Bringing those questions to a person who can see the whole picture is the heart of what we do inside a Money Roadmap.
