A retiree says he'd have millions if he invested his Social Security in the S&P 500 — here's what he's missing

Rebecca Holland

Wed, May 20, 2026 at 6:15 AM EDT 9 min read

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Sometimes things are good in theory, but not so much in practice.

And when it comes to theorycrafting your retirement, knowing what works, and if banking on Social Security is enough, can make or break your golden years.

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Imagine Jennifer, whose father, Mason, says that he would have been better off if, instead of having to pay into Social Security, he had invested that money himself.

Mason took the figures for his lifetime earnings and contributions, using the earnings history available on his my Social Security account, and then calculated what he would have earned if that money had instead been invested in the S&P 500.

He found that the total would be in the millions, and that the monthly drawdown amount he could take would be many times what he receives each month in Social Security benefits.

But a simple calculation like this doesn’t capture the full scope of a life. Here are a few points you to consider before going all in on the S&P.

Social safety net

Social Security began in 1935 during the Great Depression — the worst economic crisis in modern U.S. history — when millions of people were unemployed (1).

The political response to the dire situation was the creation of Social Security. When President Franklin D. Roosevelt signed the Social Security Act, he said, "We can never insure 100% of the population against 100% of the hazards and vicissitudes of life, but we have tried to frame a law which will give some measure of protection to the average citizen and to his family against the loss of a job and against poverty-ridden old age."

Today, Social Security keeps millions of older Americans above the poverty line. According to the Center on Budget and Policy Priorities (CBPP), without Social Security, almost four in 10 older adults would be living below the poverty line (2).

According to the CBPP, one-fifth of Social Security beneficiaries receive disability or young survivor benefits (3). The CBPP also notes that "The risk of disability or premature death is greater than many people realize. Some 8% of recent entrants to the labor force will die before reaching the full retirement age, and many more will become disabled."