When teachers think about retirement, many want to create a clear plan that includes achievable goals for life after teaching. It feels like the need to know the next step is imprinted in our bloodstream. We want to have predictable outcomes. Writing lesson plans during many years of teaching has been for many of us the best strategy to maintain a productive day in the classroom, making sure that our goals are met. We can’t change this type of thinking when we are about to retire. We want to know what life will look like when not hearing a school bell in September. It’s natural to imagine the future if we accept unpredictability as a part of our plans. However, when I was retiring, I missed this important planning in some areas of my life.
My health was the first area not being addressed properly. A long-term teaching career can put pressure on our immune system and create more vulnerability than we might have predicted. If we don’t take care of our physical and mental health, our exciting retirement plans may fall apart.
Family expectations are also often overlooked. Our spouses, adult children, elderly parents, cousins, and grandchildren have known us for decades as people who are always ready to put others’ needs ahead of our own. The empathy we feel for people has been a wonderful asset in being a teacher. Our family will not change their views about our role in their lives unless we set clear boundaries that will protect our desires and aspirations. This may cause conflicts within our closest circles, jeopardizing a carefully prepared retirement plan.
The third problem we could face after leaving work is our relationship with our friends. During teaching, we may have had enough time to maintain our friendships, but perhaps not enough to reflect on what role they played in our lives. Now, we start seeing them in a different light, and we might notice that some of our friends bring too much drama to our lives or use controlling strategies that make us feel uncomfortable. However, distancing from or leaving a friend could hinder our social life and the joy that comes with it. Being aware that we might need to adjust our social interactions after retirement could be very helpful.
The other area that should be addressed is creating time and space for meeting our dreams that were set aside during teaching, such as traveling, regular exercising, engaging in politics, or pursuing creative activities. If teaching took most of our energy for decades, our other interests were probably neglected. Do we have a physical space to do it? Do we have time, between helping our family members and maintaining friendships, to fulfill our old, but not forgotten dreams?
The final, perhaps the most important part of our retirement plan, is our identity. Do we really know ourselves? What makes us real without identifying with the societal roles as teachers, mothers, fathers, parents, wives, and husbands? What makes us happy, frustrated, peaceful, or angry? Which activities are the most satisfying? These questions became important for me when I was looking for fulfillment in my retirement years.
June of 2026 will mark my eighth year of retirement. It took about two years to resolve my health issues. Regular communication with my family members allowed me to have my own physical space and time for creative writing and painting. It came, however, with the high cost of some people feeling offended. Friend circles changed when I realized that I needed plenty of time for solitude and reflection. If we don’t answer our friend’s messages or requests promptly, only the most true, confident, and understanding people will give us space without feeling disappointed.
I never doubted while I was teaching that one day I would have time to write and paint. It was non-negotiable. Today, I feel connected to my own needs and the imagination of others when I write a poem or create a painting. But it didn’t come easily, not only because of the issues that I discussed above, but also because of a lack of knowledge on how to share my creativity in a new, highly technological world. What is common practice to us today, will be unrecognizable in less than a decade. It means that we will have to learn new skills to pursue our goals and dreams.
When I started writing and drawing in my twenties, I shared it with people in my life. I knew editors, other poets, journalists, writers, and artists personally. We shared our successes and failures during parties, chats in a coffee shop, or on the phone. Today, I connect with people in my professional field through email and social media. If I know my editor’s voice, it is because he or she posted a reel on Instagram or Facebook. I figure out what they think from their reactions to my work or from their posts. I cherish other poets and artists as a result of reading and listening to their poetry on social media or viewing their art in virtual galleries, without having heated debates in person. I love my solitude, but the closeness I had with my colleagues and friends when I was young has been missing after retirement.
Of course, we can make an effort to maintain close personal connections. Last fall, when I was enjoying my vacation in the wilderness, I met a group of retired teachers from Ontario. About ten women meet every year at the Lake of Bays to have campfires together, enjoy each other’s company, laugh, reminisce about their teaching experiences, go to a local pub for dinner, and shop together in the charming town of Hansville. Real contacts are still available—changes in technology will not take that away from us.
Even with all the planning that helps us ease into retirement, it is good to leave space for surprises. The more flexible our plans are, the more likely our retirement years will be enjoyable!
ABOUT THE AUTHOR
Anna Nike Leskowsky
Anna Nike Leskowsky is a Toronto-based journalist, poet, and a self-taught artist who came to Canada from Poland in 1990 and worked as an elementary school teacher, until she retired in 2018. She has written articles, first-person essays, modern poetry, sonnets, and haiku. Anna’s writing and art have been featured in many Canadian and international magazines and papers.
This article is featured in Canadian Teacher Magazine’s Spring 2026 issue.
