
Can AI Decide When You Should Take Social Security? A Test of ChatGPT vs. Grok
By Zach Lundak | October 20, 2025
The Results Shocked Us: Why Longevity is Not the Only Factor in Filing at 62
Are you thinking about taking Social Security at age 62? You're not alone. This is one of the most debated and complex decisions in retirement planning. To find out if the standard advice still holds true, I ran a stress test using three leading AI models—ChatGPT, Claude, and Grok—asking them to determine the optimal filing age.
I'm showing you the surprising results, the hidden costs of claiming early, and the one critical factor no calculator figures into the equation. You can also watch my video on this topic here and see some of the examples in real-time.
The AI Consensus: File Later (Longevity is King)
I asked all three models the same question: "When should I take Social Security?"
The consensus among all three was similar, with ChatGPT providing the strongest, most detailed response and Claude providing the most basic: they overwhelmingly recommend delaying benefits until 70 (or at least Full Retirement Age, FRA), unless you have poor health or a pressing immediate need.
The Traditional View: All three AIs primarily focused on a simple break-even analysis based on health and longevity. They advise filing later because the increase in the monthly check (up to 8% per year from FRA to age 70) ensures you receive the highest possible lifetime benefit, provided you live long enough to see the payback period.
The Asset Allocation Debate: Is Social Security a Bond?
Next, I asked the AIs a more nuanced question: Should Social Security be considered an asset (like a bond) when designing your Investment Policy Statement (IPS)?
ChatGPT & Claude (Traditional View): These models took a more cautious, traditional approach. They agreed you should treat it like a bond-like asset conceptually to justify a potentially more aggressive portfolio allocation, but they recommended not including it directly in your investable IPS. (It's not liquid and not on your balance sheet.)
Grok (Modern View): Grok was closer to current cutting-edge financial planning philosophy. It stated yes, you should include it as an asset. The reasoning: calculating the present value of your expected Social Security benefits allows you to conclude that you can sustain a higher equity allocation in your investible portfolio, promoting a more integrated and efficient retirement strategy.
The Takeaway: For investors with substantial surplus assets, treating Social Security as a bond equivalent opens up part of your liquid portfolio to potentially be more aggressive, maximizing growth elsewhere.
The Elephant in the Room: The 2033/2034 Deadline
What about the threat that Social Security will be bankrupt in 2033 or 2034? All three AIs addressed this with cautious political optimism:
AI Conclusion: All models agreed that some adjustment or reform will occur before 2033 due to the political importance of Social Security.
The Risk: However, they also warned that if Congress fails to act, a 20-25% reduction across the board is well within the realm of possibility per current projections.
Historical Context: As Grok pointed out, similar shortfalls in the past (1983) were solved by a combination of rising payroll taxes and benefit adjustments for future (not current) retirees.
The Missing Factor: The Utility of Money
While the AI models are strong on longevity, they fail to account for a massive human factor: The Utility of Money.
The Concept: Dollars received earlier in retirement often have a higher utility factor associated with them because people are generally much healthier and more active in their early sixties than in their late eighties.
The Advantage of Early Funds: You can use money earlier for big, physical goals—like world travel, buying a boat, or taking care of family—that may not be possible later due to health constraints.
The AI Flaw: Since the AI models only use longevity as the sole indicator of when to file, they miss the value of using some of that benefit earlier to maximize your healthspan and overall life satisfaction.
The best filing decision must balance the statistical certainty of longevity with the emotional reality of how much you need money now versus later.
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