Can You Use AI to Plan Your Retirement? What It Gets Right, and Where It Falls Short
AI can be a brilliant research partner. But it isn't a fiduciary, and it doesn't know when it's wrong.
He'd spent the better part of a Saturday with it — back and forth, refining, asking follow-up questions. By that evening, he had a full retirement plan: a withdrawal strategy, a Roth conversion schedule, even a month-by-month budget. “It was the most productive planning session I've ever had,” he told Kevin Lum a few days later. “And it didn't cost me anything.”
Then Kevin asked him one question: “What did it assume about your Social Security claiming age?” He didn't know. Neither, as it turned out, did the plan account for it correctly.
Kevin sees this more and more — smart, capable people using AI to build retirement plans that sound completely authoritative and are quietly wrong in ways that are easy to miss until it's too late to fix them cheaply. More than half of American adults have already asked an AI tool for financial advice, more than have ever sat across the desk from a human advisor. So in his video “I Asked AI to Plan My Retirement — Then I Caught it Lying,” Kevin decided to actually test it: where does AI get retirement planning right, where does it fall apart, and how should you use it if you're going to use it at all? What he found became a framework you can use yourself.
Five Things to Know Before You Trust AI With Your Retirement
AI isn't useless for retirement planning. In some ways, it's better than people expect. But it has real, well-documented blind spots. Work through these honestly before you let it guide a real decision.
1. It Gets the Big Picture Right
Researchers at MIT Sloan School of Management built a simulated human financial life spanning age 22 to 90 — earnings, savings, investing, taxes, random life events — and ran real people's AI-generated retirement advice through thousands of simulated lifetimes. The guidance held up: save more while working, draw down in retirement, stay diversified in stocks while young, dial back risk with age. AI even outperformed people's own instincts in one area — only 6% of users thought to ask about liquidity, but AI raised it in 83% of its answers.
Ask yourself: Am I using AI for broad principles, or am I asking it to make a specific, high-stakes decision?
2. It Breaks Down on the Math
AI tools don't calculate. They predict the next likely word based on patterns. That's a meaningful problem in a retirement plan built from thousands of interconnected numbers. Kevin spent weeks trying to build a retirement calculation engine using AI, checking it against numbers he knew to be correct, and it was consistently off, particularly on tax optimization, withdrawal sequencing, IRMAA surcharges, and Social Security, which researchers note is governed by roughly 22,000 pages of rules. He compares it to a home stereo project: using AI to research components felt brilliant, until a new variable was introduced and the whole plan devolved into contradictory, chaotic advice. The more moving parts a decision has, the less trustworthy the answer gets.
Ask yourself: Does this decision involve more than one variable — taxes, timing, and income — interacting at once?
3. It Can Quietly Amplify Your Blind Spots
The same MIT research found that answer quality depends heavily on who's asking. People with lower financial literacy, based on how they phrased questions, ended up with worse simulated outcomes. More troubling: prompts written by women led to less simulated wealth than prompts written by men — and when researchers added the phrase “I am a woman” to an identical prompt, the AI recommended a lower stock allocation. AI doesn't just answer your question. It can reflect an assumption back at you and reinforce it.
Ask yourself: Would I get a different answer if I described myself, or my situation, differently?
4. It Will Rarely Admit It's Guessing, Unless You Ask
In one test, three AI tools all said a hypothetical retirement at 65 was “tight but doable.” Only after being asked what assumptions were used did one admit it had assumed the person would live to just 90, hadn't modeled taxes accurately, and had priced in no long-term care at all, ultimately revising its answer to “meaningfully underfunded.” The reassuring answer comes first. The honest one shows up only when it's challenged.
Ask yourself: Have I asked it to state its assumptions — or to explain why I might be wrong — before trusting the answer?
5. It Doesn't Know When You Need a Human
AI carries no fiduciary responsibility. It doesn't bear any consequence when it's wrong, and it can't reliably navigate the edge cases of Social Security or a true tax-efficient withdrawal strategy. More importantly, Kevin's experience with hundreds of clients is that the biggest obstacle to a good retirement usually isn't a knowledge gap. It's fear: fear of investing, fear of spending money that's already been saved. AI can hand you a flawless-looking spreadsheet and still not move you past the anxiety actually driving the decision.
Ask yourself: Is this a decision I'm comfortable getting wrong, or one where I need someone accountable for the answer?
Watch the Full Breakdown
Kevin walks through his full test, including the exact conversations where AI got caught guessing, in his video “I Asked AI to Plan My Retirement — Then I Caught it Lying.” If you're already leaning on AI for your own planning, it's worth watching in full.
Want a faster read on your own numbers before your next move? Check to see if you’re on track for retirement using our Free 5 Minute Retirement Plan Calculator
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FAQs: Using AI for Retirement Planning
Can I use AI to plan my retirement?
Yes, as a starting point. Research from MIT Sloan found that AI tools like ChatGPT and Gemini give general guidance — save more, diversify, draw down in retirement — that tends to be sound. But because AI predicts likely-sounding answers rather than performing true computations, it can sound just as confident when it's wrong, particularly on tax optimization, Social Security timing, and Roth conversion strategy. Treat its output as a first draft, not a final plan.
Can AI retirement advice be biased?
Yes. MIT Sloan researchers found that answer quality depended on how financially literate a question sounded, and, more troubling, on the asker's gender. Prompts written by women led to less simulated wealth than prompts written by men, and when researchers added the phrase “I am a woman” to an identical prompt, the AI recommended a lower stock allocation. AI can reflect an assumption back at you and reinforce it rather than challenge it.
Should I still hire a financial advisor if I use AI tools?
Yes. Most retirement planning failures aren't a knowledge gap. They're behavioral: fear of investing, or fear of spending money that's already been saved. AI can produce a flawless-looking spreadsheet and still not move you past that anxiety. A human advisor addresses that side of the decision, and carries accountability for it, in a way a chatbot cannot.
How can I get better retirement advice from an AI tool?
Three habits help: ask the AI why you might be wrong instead of whether you're right, ask it to state the assumptions behind its answer, and ask it to act as an adversarial reviewer of any plan it produces. Running the same question through two different AI platforms and comparing results can also surface errors a single tool misses.
Kevin Lum, CFP® | Retirement Made Simple
This article is companion content to the Retirement Made Simple YouTube channel. It is for informational purposes only and does not constitute personalized financial advice.