Failure on the Open Road and Learning to Love the Banana Peel

I have always believed that life gives us little nudges when we need them. Sometimes they show up as a gentle whisper in the breeze as I walk Rigby in the park. And sometimes it's a mishap so ridiculous you can’t help but laugh. Like showing up for pickleball league last night, pulling off my sweatpants, only to realize I forgot to put on my shorts.

Lately, as I’ve been working through the first full edit of my retirement book, I’ve realized that most of the wisdom I have collected didn’t come from getting things right. It came from the clumsy, crooked, deeply human moments where I absolutely did not stick the landing.

Which brings me to a quick update: the first full draft of my next book is officially done.

Typed. Saved. Backed up in the cloud because I have learned not to tempt fate. I am now deep into the editing process, which so far has included equal parts tightening language, rethinking transitions, and asking myself, “Who wrote this sentence, and what were they trying to say?”

I’m also exploring publishing options. From a mix of traditional routes to hybrid models and the increasingly tempting “let’s do this myself and keep the creative freedom” approach. I’ll share more as that journey unfolds. But for now, this felt like the perfect moment to talk about something that has shaped every stage of this project, and every chapter of my life, retirement included.

Failure.

Not the big, dramatic kind with fireworks and collapsing buildings. Just the everyday stumbles that teach us who we are.

And in the spirit of embracing failure, here’s a word-for-word snippet from the fourth chapter of my new book. It’s a story about my father, his hopes, and the gentle ways life teaches us to let go of some of our dreams.

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Excerpt from Chapter 4

As a physician, my father had a lifelong passion for science and research. Naturally, he hoped to pass that legacy on to his children. Maybe one of his two sons would follow in his footsteps and pursue a career in medicine. Then came high school biology, chemistry, and the grades that followed, and that dream quietly died on the classroom floor. Strike one.

My father was also a patient man. Years later, two grandsons arrived, and like a phoenix, his dream rose from the ashes. Now retired from research, he gifted his prized microscope to his first grandson. They spent a couple of joyful afternoons viewing slides together until the microscope was quietly retired to the basement, never to see the light of day again. Strike two.

Bottom of the ninth. One pitch left. Maybe his youngest grandson would keep the dream alive and choose a path in science or medicine. Then reality came crashing down on him. Over lunch during a summer visit, the final pitch was thrown. Without prompting, his last great hope, having planned his future career at perhaps eight or nine years old, made his big announcement: “When I grow up, I want to be a garbage man.” Swing and a miss. Strike three.

I give my father tremendous credit. He didn’t sulk or spiral over what some might have called a personal failure. I like to think he learned from that little banana peel tossed into the arc of his story. He came to appreciate his sons’ career paths and marveled at his grandsons’ unique accomplishments. Science and medicine were his passions to pursue, not anyone else’s to inherit. Setbacks happen. We stumble, we learn, and we keep moving toward better days.

That moment still makes me smile, but it also reminds me how deeply personal our experience of failure can be. It made me reflect on how we perceive failure in our culture, how different organizations approach it, and why the fear of failure, especially later in life, can hold us back from moving forward.

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Where We Learned to Fear Failure

Somewhere along the way, usually around the time we were handed a report card or told not to color outside the lines, society taught us that failure is bad. Not just “needs improvement,” not just “let’s try this again,” but a full-on reprimand. Schools rewarded the correct answers and punished the wrong ones. Early jobs reinforced that pattern through performance reviews, metrics, quotas, and all the subtle signals that mistakes were threats, not stepping-stones.

By the time we reached midlife, the message was baked in: Failure equals falling behind. Falling behind equals losing. And losing equals… well, don’t even think about it.

For decades, many of us operated inside that tight little box, doing everything possible to avoid the missteps that might cost us promotions, credibility, or security.

But retirement, unexpectedly, hands us a chance to unlearn all of that.

It hands us space. It gives us permission. It offers us the freedom to make a mess, call it progress, and start again the next morning with a smile and a second cup of coffee.

Failure as a First Draft

The rest of Chapter 4 (Banana Peels and Other Slippery Slopes) expands on this idea: failure isn’t the end of a story. It’s the beginning of a better version.

Think about it:

• A failed experiment in a lab isn’t a defeat. It’s data.

• A wrong turn on a road trip doesn’t ruin the journey. It creates a memory.

• A sentence that doesn’t quite land isn’t a sign to quit writing. It’s a sign to revise, rethink, and try again.

Failure is feedback. It’s coaching. It’s the universe saying, “Not quite, but you are getting warmer.”

More importantly, failure strips away the pressure to be perfect and leaves room for possibility. That’s where the good stuff hides.

My father didn’t raise any scientists, but he raised kids who weren’t afraid to try, to explore, to risk being terrible at something before getting better (Exhibit A: my early years of karate training). For me, failure wasn’t a verdict. It was part of the process.

In retirement, and honestly, in any new chapter, that matters.

What This Means for the Road Ahead

Finishing the first draft of this book was a milestone, a big one. But the real work, the real growth, is happening now in the editing process. That is where the failures show up. That is where the weaknesses get exposed. And that is where the story becomes stronger. At least that is what I keep telling myself each morning as I sit down at my desk.

We spend so much of our professional lives thinking that failure is a threat, something to be avoided at all costs. Retirement, oddly enough, gives us permission to flip that script.

Try something new. Be terrible at it. Smile. Adjust. Accept that you need to play pickleball in your sweatpants tonight and try again another day.

The wrong turns are part of the story. Sometimes they are the story.

And So…

Thanks for staying on this journey with me. For supporting the writing, the reflecting, the false starts, and the small wins. I’ll keep you posted on the publishing path as it takes shape, but for now, I am embracing the process (a nod to every professional sports coach) and the difficulty of editing and revision.

And remembering, maybe even believing, that somewhere out there, my father is smiling, still hoping that one of us will eventually figure out that microscope.

Dan Troup is The Sunny Side of 57. He loves to reflect and write about life, family, career, and retirement. Check out more of his reflections on his blog site. Also, consider subscribing to The Sunny Side of 57. When not playing pickleball or hiking with Sue and Rigby, he (tries) to write a new post one to two times a month.