Retirement Reflections: Stories and Lessons Learned

September 6, 2025

Standing on our dock by the lake, we engaged in conversation with a woman paddling in a kayak. She introduced herself by sharing that she had just retired at the age of fifty-six after teaching for thirty-two years at the high school level. She expressed that the energy to get up in the morning and face her students was no longer there. Although she didn’t have a specific plan for her retirement yet, she was enjoying exploring the lake by boat and getting involved in her community’s social activities. She hoped she had made the right decision to retire and not work longer.

In contrast, when I had a tooth extracted the next day, the technician said she enjoyed her job and has yet to consider retiring after spending forty-two years in the office.

I compared the experiences of these two people with the retirement of some family members. My cousin secured a job right after graduating from university and spent decades enjoying his work without giving retirement a thought. However, he lost his job at age 76 due to organizational downsizing. He sought similar positions elsewhere but was unable to find one, even with the help of a job hunter. So, he turned to podcasting about making drinks with his dog as an observer and taster, keeping him engaged. Another example was my mathematician brother, who dedicated his life to teaching and writing papers until his passing. He never pursued hobbies; to him, mathematics was his passion.

These examples prompted me to reflect on whether there is an ideal age to retire. I thought of a couple of friends who retired in their early fifties.

One friend started a business after retirement, at age fifty, inspired by his passion for photography. The company closed within a year, likely because the goals he set were difficult to attain. After that experience, he took on a volunteer responsibility of leading the local photo club for several years. Eventually, he and his wife purchased timeshares in the Caribbean and began cruising around the world. His interest in photography, cruising, and staying at timeshares has ebbed recently.

Another friend retired at age fifty-four. During the summer season, he cycled and became the leader of the local bicycling club. During the winter season, he and his wife traveled internationally until they decided to stay in Mexico during the winter to escape the cold Canadian winters. His cycling days are over, but they still go to Mexico for the winter.

Both friends retired thirty-two years ago, which, in one case, is longer than the length of his working life.

Interestingly, both individuals tend to express conservative views on topics such as politics, crime, and the environment. In particular, I am surprised to hear from one that climate change is not real and from the other that environmental studies are a waste of money. Were my friends consistently conservative, or have they become so after a long period of retirement?

It is also noteworthy that both of these friends had employment with one organization from their college graduation to their retirement. And they did not seek out another job after leaving their first and only job in their career. They retired relatively early, possibly because their roles within their workplace no longer provided sufficient challenges, or there may have been incentives for them to leave.

My experience has been different. I moved from working in the public sector to the private sector and then to my own consulting business. I enjoyed all of my jobs, public and private, and continued working until much later in life than many people.

In my last career as a consultant, the work was very exciting and interesting until I acquired some clients whom I found unpleasant to work with. I also started traveling, and other hobbies gradually took priority, making the consulting work less appealing. No question, changing jobs and facing new challenges made work enjoyable and satisfying.

I have always sought something meaningful in my retirement, such as international charity work and writing a memoir, which prompted me to take writing courses to improve my writing skills. The most boring time for me is when I have no projects on the go. Paradoxically, that is also the time for dreaming up new projects.

My conclusion on the subject of retirement is that if you are happy with your work, keep on working.

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