I Asked ChatGPT for the Worst Social Security Mistakes Retirees Make — And How Not To
Written by
Jordan Rosenfeld
Edited by
Molly Sullivan
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Like many things that fall into the retirement bucket, retirees often wait to think about the ins and outs of Social Security until they decide to claim it. However, everyone should educate themselves on how Social Security works well before it’s time to claim, so you can make it part of your retirement strategy and not get caught by surprise.
While there are many possible mistakes that are easy to make regarding Social Security, I asked ChatGPT to drum up the ones with the worst repercussions for retirees, so you can avoid them.
Claiming Too Early
It’s common to want to retire as early as possible, before full retirement age of 67. However, claiming Social Security benefits at 62, the earliest year you are eligible, simply because it’s available, without assessing longevity, health, income needs or other assets can be a big mistake for some, ChatGPT said. When you claim early, benefits are reduced — by as much as 25% to 30% compared with full retirement age, and the cut is permanent.
ChatGPT suggested that retirees considering this should first run claiming scenarios at three stages: age 62, full retirement age and age 70. If you’re healthy, expect longevity and have other income sources, delay as long as you can. Use early benefits only if cash flow or health truly requires it.
Benefits increase roughly by 8% each year, adjusted for inflation, so the longer you delay, the more you get. In practical terms, ChatGPT framed Social Security as a guaranteed, inflation-protected income stream rather than a short-term cash decision.
Not Coordinating With Your Spouse
Another mistake occurs when spouses claim benefits without considering how those decisions affect each other. The lower-earning spouse may end up with a permanently smaller survivor benefit if the higher-earning spouse claims early at a reduced rate. It’s best to prioritize the higher earner delaying their benefits, when possible, ChatGPT advised. Survivor benefits are based on what the higher-earning spouse was receiving at death, making coordination especially important. Always factor survivor benefits into retirement security and model scenarios that account for both spouses’ lifespans.
Overlooking Taxes on Benefits
Another common mistake is assuming that Social Security is tax-free. Depending on how much income you have in retirement — including that which you withdraw from your retirement accounts — up to 85% of benefits can be taxable depending on income. This taxation is determined by “provisional income,” which includes adjusted gross income, tax-exempt interest and half of Social Security benefits.
To avoid taxes taking a big bite out of your Social Security benefits, get educated on provisional income thresholds, ChatGPT urged. When possible, coordinate withdrawals from taxable, tax-deferred and Roth accounts. And for those who can, consider Roth conversions before claiming benefits.
Some retirees also keep working part time, unaware that they are pushing themselves over the threshold for taxation. So, knowing how work income interacts with benefits before claiming can prevent unexpected tax consequences.
Treating Social Security as Standalone Income
While there are cases where Social Security is the only income a retiree can reliably count on in retirement, it puts a retiree in a tough financial position. ChatGPT warned that treating Social Security as standalone income without integrating it into a broader retirement plan can increase taxes, reduce portfolio efficiency or force unnecessary early withdrawals.
The solution requires saving for retirement in other accounts and coordinating Social Security with Medicare timing and tax strategy. It’s best to view Social Security as part of an interconnected system, not a single isolated choice, the AI said.
Claiming Without Strategy
The biggest Social Security mistake isn’t claiming early or late — it’s claiming without strategy, ChatGPT said. Social Security decisions are permanent, inflation-linked and intertwined with taxes, longevity and spousal benefits. Retirees who treat claiming as part of a coordinated financial plan tend to avoid the most expensive errors and gain more lifetime income.
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