Retirement Isn't a Problem to Be Solved: Why I Chose Not to Write Another Retirement How-To Book

About a year and a half ago, I was talking with my daughter-in-law, Caroline, about ideas for my next writing project. She suggested that I write a book about retirement. She was thinking of a self-help guide. I was thinking about something else entirely.

Walk into any bookstore or search Amazon for retirement books, and you'll find plenty of advice. How to retire. How to invest. How to travel. How to stay active. And, of course, the ten-step formulas for creating the perfect retirement. There is certainly value in those books.

But that's not the book I chose to write.

Because retirement isn't always a problem to be solved.

Sometimes it's an experience to be understood.

In fact, I didn't set out to write a book about retirement at all.

I started writing because I had questions I couldn't easily answer. Questions that showed up quietly at first and then more persistently once the structure of work was gone. I had spent decades in a world where progress was measurable, where the days were full, and where I always knew what I was working toward.

And then one day, I didn't.

What I found wasn't just free time.

It was space.

Space to think, to reflect, and to take a closer look at parts of my life I had spent years moving past too quickly.

For me, retirement felt a little like standing in front of a painting in a museum. Five people can look at the same painting and walk away with five completely different interpretations.

Retirement is much the same way.

Your version won't look exactly like mine, and mine won't look exactly like yours.

Yet while the details may differ, many of the feelings are surprisingly similar. The loss of identity when the career chapter ends. The disappearance of routines that shaped our days for decades. The absence of the metrics and scoreboards that once told us how we were doing. Questions about purpose, relevance, connection, and what comes next.

These are things many retirees experience, yet we don't talk about them very often.

Maybe it's pride.

Maybe it's embarrassment.

Maybe we simply assume we're the only ones feeling them.

I began writing as a way to make sense of that transition.

At first, it was just for me. Then for my family. And eventually, for anyone else who might be asking the same questions, even if they hadn't quite found the words for them yet.

Somewhere along the way, I realized I wasn't writing about retirement as much as I was writing about identity.

About what remains when the roles and routines that once defined you begin to fade, and how you start to piece together something new from what is left behind.

When I retired at 57, I wasn't looking for another checklist. I wasn't trying to optimize my morning routine or create the perfect retirement plan.

What surprised me were the questions I never expected to ask.

Who am I when my career is no longer part of my identity?

Why do I feel restless when I finally have the freedom I've worked toward for decades?

Why do some days feel full of possibility while others leave me wondering what's next?

Those questions eventually became the foundation for A New Game Without a Scoreboard.

It's not a self-help guide.

It's simply one person's honest account of navigating the transition into retirement. The victories, the doubts, the unexpected lessons, and the realization that retirement is often far more complicated, and far more interesting, than the brochures suggest.

The book doesn't try to provide answers for everyone.

But if parts of my story feel familiar, perhaps you'll discover that you're not as alone as you thought.

A New Game Without a Scoreboard launches on July 14. The Kindle edition is available now for pre-order, and a free chapter is available for those who would like a preview.

Dan Troup writes The Sunny Side of 57, where he shares reflections on life, family, career, and retirement. His upcoming book, A New Game Without a Scoreboard, explores what happens when the structure of work fades and questions of identity, purpose, and belonging take its place. When he’s not playing pickleball or hiking with Sue and Rigby, he’s usually thinking about the next post, even if it only shows up once a month.