At 49, I Expected My Boss’s Retirement to Be Just Another Office Day — Instead His Leadership and Kindness Made It the Most Important Moment of My Career

Retirement parties are usually cake, a slideshow and a handshake. But for many baby boomers, leaving work is also the first time they look back at how they treated people. In a recent Traliant survey of more than 2,000 U.S. employees, about one in five said they had been mistreated at work in the past 5 years, and fear of retaliation was the top reason people stayed quiet. Sometimes wisdom comes with aging, and sometimes it takes a grandchild and a little empathy to arrive.

Theresa K., 49, a claims adjuster from Milwaukee, Wisconsin, learned that an apology can come 17 years late with an act of kindness and still matter.

I started at a regional insurance agency in Milwaukee’s Third Ward in March 2009. I was 32, newly divorced, and my daughter Mia was 3. I needed the health insurance more than I needed to like my boss. Rick D. was my manager for most of the next 17 years. He brought kringle on Fridays and had pictures of his grandkids all over his cubicle wall.

He also winked at me. In my second year, he stopped at my desk and said my skirt looked “great on my body.” I laughed it off and never wore that skirt again. I didn’t laugh at his other jokes either, which is how I ended up with the office nickname “Saint Theresa.” I never went to HR. I needed the job, and it didn’t feel big enough to report. That’s what I told myself, anyway. Self-compassion wasn’t really in my vocabulary back then.

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His retirement lunch was Friday, June 26, in the big conference room. Costco sheet cake, maybe 40 of us. Rick gave the usual speech. He joked that he was the last baby boomer in claims. He said he and his wife were going to be full-time grandparents now, since their son had just given them a third grandkid. “People say wisdom comes with aging,” he said. “Mostly you just start looking back.”

Then he said, “I regret that some people acted like saints here.”

A couple of people glanced at me. My face went hot. I thought he was taking one last shot at Saint Theresa in front of everyone.

He looked down and said, “I was one of them. And I need to apologize to a few people. You know who you are.” A few people laughed. Linda from billing didn’t. Neither did I.

At 4:30 he came to my desk carrying his box. “That was about you,” he said. “The winking. The skirt thing. All of it. I knew it was wrong and I did it anyway because nobody stopped me. I’m sorry.”

I didn’t say it was okay. I just said, “Okay.” In 2019 our VP had asked him who should be the next team lead, and Rick had said I wasn’t ready. “You were ready,” he said. “I didn’t want to lose you on my team. I told Dave the truth this morning and said you should get my job.”

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His granddaughter had started her first office job in Chicago in January, and every time she mentioned her boss, he got a knot in his stomach. “She taught me more empathy in six months than 40 years of managing people did.”

In the parking garage, Linda was waiting by my car. She’s 58, in billing since 1996, with the wisdom of 30 years in one office. “Was it you too?” she asked. We sat in my car and talked for an hour. She showed me more empathy than I’d ever shown myself. “You had a kid and a car payment. You didn’t do anything wrong by surviving.” That was the first time I tried a little self-compassion instead of anger.

I interviewed for Rick’s job in July. I got it and started on September 1 with an $11,000 raise. My first request to HR was to replace our 20-minute harassment video with real training built on empathy. Linda and I wrote the examples. Mia, now 20, keeps telling me to practice self-compassion, which is funny coming from her.

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Last month, Rick mailed me a card from Door County, with a photo of two retired grandparents and their grandkids on a dock. It said, “Proud of you.” I haven’t decided if I’ll write back. But I kept it.

Theresa’s story teaches us all that wisdom can show up late, and that empathy often comes from the person sitting next to you. Aging doesn’t erase the past, but for baby boomer grandparents heading into retirement, owning a mistake might be the most useful thing they leave behind. And for anyone who stayed quiet to keep a paycheck, self-compassion isn’t an excuse. It’s where moving on starts.

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Has an apology ever changed how you saw your past? Tell us in the comments.

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