Oct 10, 2026

I Retired Late and Regret It — Here's Why I Wish I Would've Done It Sooner

Written by Laura Beck
|
Edited by Laura Beck
I Retired Late and Regret It — Here's Why I Wish I Would've Done It Sooner

Tim T. taught middle school for 40 years and didn't retire until he was 72. People used to tell him he'd know when it was time to stop.

The thing is, he never felt that moment arrive, and looking back, that's exactly the problem.

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“Walking away from a classroom felt like giving up a piece of who I was,” he said. “I was good at my job, and being good at something is a real confidence boost.”

The issue? He was missing time with his family and friends. 

“My husband passed away not long after I finally did retire, and the extra years I spent in the classroom are years I can't get back with him,” he said. 

Tim added that he kept telling himself that he and his husband would travel more once he retired, but that didn’t have a chance to happen. 

For anyone weighing the same decision, there are a few practical details that are worth understanding.

Social Security benefits stop earning delayed retirement credits once you reach 70. That means there is no additional increase from delaying your claim from 70 to 72. Working past 70 can still increase your eventual benefit if your new earnings replace one of the lower-earning years in the 35-year earnings record used to calculate benefits, but the increase depends on the person's earnings history.

In other words, Tim didn't need to keep working until 72 simply to earn a larger Social Security benefit through delayed retirement credits. He could have stopped working earlier and still waited until 70 to claim Social Security, although retiring earlier would have meant giving up additional wages and potentially some additional retirement savings.

It's also worth noting that Medicare enrollment also needs attention for people who work past 65 (while covered by an employer's group health plan). If you have qualifying employer coverage, you can generally delay Part B and then use an eight-month Special Enrollment Period after the employment or coverage ends, whichever comes first. Missing the applicable enrollment period can result in a Part B late-enrollment penalty that generally continues for as long as you have Part B.

“Being good at a job and loving it aren't reasons to stay past the point where it costs you something bigger,” said Tim. 

He adds that he doesn't regret the decades he spent teaching, he just regrets how long he waited to stop. Armed with the proper information about both his benefits and his life, he would've made different choices.

This article was provided by MoneyLion.com for informational purposes only and should not be construed as financial, legal or tax advice.

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Written by
Laura Beck
Edited by
Laura Beck