Lifestyle

Phil, 66, Had a Teaching Career and a Retirement Plan. Then He Took a Job at Home Depot: “Let Me Be Clear, This Wasn’t the Plan”

By Mike Harper · November 13, 2026

Phil did not want to make this video.

The retired teacher behind the YouTube channel What’s Up Boomer (@whatsupboomer1958) says he avoided the subject for a long time, even though he knew it was part of his retirement story. In the video, posted in May 2025, he introduces himself plainly: “My name is Phil. I’m 66 years old. I’m retired and I’m working at Home Depot.”

“Let me be clear, this wasn’t the plan,” he says early on. After careers in teaching and corporate sales, his idea was to collect Social Security, not to go to work at a home improvement store.

He is honest about why he waited to talk about it. Phil says the hesitation came from “a level of embarrassment, shame even, that here I am working at Home Depot.”

He also pushes back on the idea that he failed. Phil says he had a plan and financial knowledge, and that landing at the store was not the result of bad decisions. It was the way life turned out.

After he left his last corporate job over a change in direction, Phil says he was off work for a couple of months. Without savings to carry him for the rest of his life, he started thinking about what to do next. A neighbor who worked part time at the store told him they would hire him quickly.

“I put an application in and I got hired in a heartbeat,” he says.

He asked for the lumber department, hoping to get back in shape, but says he was 62 or 63 and the interviewer steered him to customer service. “I ended up at the service desk,” he says, and he calls that a relief.

Phil says he started part time. Within a month he was offered full time as a closer and turned it down. Months later, working close to full time anyway, he decided to add one more day so he could qualify for the company’s benefits.

He spends much of the video on what he gained. The few months he was home alone wore on him, he says, and the job became an immediate boost to his social life. He now has regulars at the desk who ask about his grandkids. The downside, in his words, is that “you don’t control your time.”

Phil is far from alone. The Social Security Administration says on its Receiving Benefits While Working page that people can work and collect retirement benefits at the same time, but there are limits before full retirement age.

For 2026, the agency says, a person under full retirement age for the whole year loses 1 dollar in benefits for every 2 dollars earned above 24,480 dollars. In the year someone reaches full retirement age, the agency deducts 1 dollar for every 3 dollars earned above 65,160 dollars, counting only the months before that birthday. Starting the month a person reaches full retirement age, earnings no longer reduce benefits.

The SSA also says withheld benefits are not simply gone. When a worker reaches full retirement age, the agency recalculates the benefit to credit the months that were reduced.

Anyone thinking about a job after claiming can check their full retirement age and run the numbers with the SSA’s earnings test calculator before taking on more hours. Phil’s advice is simpler. He says there is no one right way to do retirement.

This article is for general information and is not financial or legal advice. Phil’s story and quotes are from his own YouTube video; Social Security rules are as stated by the Social Security Administration. This article was produced with the assistance of AI and fact-checked against the sources cited by LightWave Reports.