Restless in Retirement

I found “not working” wasn’t working for me

Tom McHale
Crow’s Feet
4 min readJan 23, 2024

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Photo by Michael Heuser on Unsplash

I retired in July 2023 after 25 years of teaching. My hobbies include fly fishing, hiking, writing, reading, cooking, and gardening. I’m also an active member of a couple of organizations I care about. So, I anticipated that my wife and I would have a happy, active life in retirement.

But that’s not what happened.

When October rolled around, I found myself asking: Is this it? Is this what I worked all my life for? I found it difficult to motivate myself. I was stagnating. I missed the energy of the classroom.

So, in November, I took a job as a secondary floating substitute teacher in the district where I live. Every morning, I get an email that tells me which of the five district middle schools or three high schools I should report to. Since many of my hobbies are warm-weather activities, this would give me something to do in the wintertime, let me work with students again, and bring in some money.

And yet, as the New Year rolled around, I still felt restless and unfulfilled.

Friends and family don’t understand why I would go back to work. Retired friends gush about how great it is to wake up and know you can do whatever you want.

So why don’t I feel the same joy in being freed from the expectations, responsibilities, and work deadlines?

Enter The New Old Age

In last month’s Atlantic magazine, I stumbled across an article by David Brooks titled The New Old Age: What a new life stage can teach us about meaning and purpose — before it’s too late. The article examines “Encore programs” at some of the country’s elite universities that help recent retirees “figure out what they want to do with the rest of their lives.” I connected with the profiles of some of the attendees who were experiencing similar struggles. Woven in with their stories are quotes from business consultants, psychologists, and theologians.

For example, business consultant William Bridges believes that life transitions like retirement involve a period of loss, a neutral zone, and a rebirth. “People in the neutral zone don’t yet know who the new version of themselves will be,” Brooks writes. “They report feeling hollow, disoriented, empty.” This seems to be an accurate description of how I’m feeling.

Preparing for Rebirth

So for those of us stuck in neutral, how do we find our rebirth? That’s what these Encore programs focus on. They do this by having students complete activities designed to help them reflect on three foundational questions: Who am I? What do I really want? What should I do?

I began pondering the first question in a previous Medium article: Who Am I Now?: Reflections on retiring from the classroom. I still have much more to do in this area, but I’ve discovered a few things. Collaboration, especially as part of a creative team, is essential to who I am and what I’m missing. I’ve also realized how important relationships are to who I am. Being cut off from the almost daily interaction with students and colleagues has left a void I need to fill. I am also a lifelong learner and need to find ways to expand my experiences, understanding, and point of view.

What do I really want?

For the second question, Brooks says students in Encore programs are encouraged to move “from pursuing the extrinsic desires the world rewards to going after their intrinsic desires.” Often, this can involve revisiting dreams we gave up long ago to pursue the demands of adult life.

I spent most of my twenties and early thirties pursuing a dream of being involved in music. In the early 1980s, I pursued a degree in music technology at New York University before dropping out. After that, I played keyboards in a band and helped build a small analog home studio. I would lose track of time when recording, editing, and performing.

The interaction of playing music with others was something I greatly enjoyed and would like to experience again. I recently bought a new keyboard, and I’m trying to reacquaint myself with the instrument after all these years. I’m not sure where all of this will lead, but it makes me feel like I can better fill the time and freedom that retirement provides.

What should I do?

Brooks claims that students in the Encore programs have chosen purpose over leisure. Perhaps that is ultimately what I’m missing. Certainly, teaching gave me a purpose, which would explain why I wasn’t finding my rightfully earned life of leisure fulfilling.

Brooks puts it this way: Most of us don’t just want simple happiness; we want intensity. We want to feel that sense of existential urgency you get when you are engrossed in some meaningful project, when you know you are doing something important, and good.

I definitely see some truth in this — at least for myself.

I’m not sure what meaningful project I might take on in retirement. I know I want to give back in some way. I know I want to cultivate and expand my relationships with friends and family. I know music and nature need to be a more significant part of my life in the future. I know I want to learn more, especially about issues and topics that matter to me. I know I want to do more.

I’ll figure out the rest along the way.

I invite you to follow my journey and contribute your thoughts and experiences.

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Tom McHale
Crow’s Feet

Student Voice and New Voices Advocate, Anti-Racist Educator. Retired journalism/English teacher. I write about education, music, and media.