The Dog Didn’t Eat My Blog. The Book Did. Or Thoughts from O'Hare Airport.

It’s been a little quiet around here at The Sunny Side of 57. Seven months since my last post (but who's counting). And no, I haven’t retired from retirement. I’ve just been busy doing something I never expected to be doing in this chapter of life: writing a book.

What started as a few reflections on this blog has grown into something bigger, more structured (well, mostly), and more personal. It’s still me, still sunny-side-up, but with a deeper dive into what life after career really looks like and feels like.

The current working title (which I seem to change on a monthly basis) is:

Retired, Reflecting, and Still Becoming:

Conversations on Retirement, Second Acts, and the Road Ahead

If it sounds like a mouthful, that’s because it is. But it’s also the most accurate description I could come up with for this strange, liberating, and sometimes disorienting journey that retirement has turned out to be for me.

My book is not a how-to guide filled with bullet-pointed steps to achieve your best life in retirement. It’s more like a conversation on a bar stool or on the dock at the lake, where we talk about purpose, invisibility, reinvention, money anxiety, letting go of titles, and what in the world to do with all this “free” time. It’s part memoir, part reflection, and part invitation for you to rethink what’s next on your terms.

The book is composed of themed chapters that each tackle a different aspect of the retirement experience. Some humorous, some emotional, all grounded in personal stories (and, yes, occasional walks with Rigby and lake views from Central New York).

Think Dan Troup meets Jimmy Buffett and Mitch Albom. But instead of asking for their autographs, he asks for a bit of advice on book writing.

Today, I would like to share a portion of a chapter that holds a special meaning for me. One that speaks about what happens when your world suddenly gets quieter, even though you're sitting amongst the chaos of Chicago’s O’Hare airport.

It’s from Chapter 6, and it’s all about visibility, identity, and how retirement can sometimes feel like stepping off the stage and into the shadows. Below is a portion of the chapter.

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Chapter 6: Invisibility, Airports, and the Edges of Mortality

Settled. I think that is a word I would use to describe myself now, almost a full decade into my retirement. Most days, “Retired Dan” is a happy camper, settled in retirement with a sense of purpose, comfortable in his own skin, relatively content and stress-free. I have my health, the love of my wife and family, and enough purpose and activities to keep boredom at bay. Life is good.

And then I go to the airport.

I never served in the military, so I can’t speak with any authority or personal experience about what it must be like to live with any form of PTSD. And yet, I do understand how a place or an environment can trigger intense and powerful emotions. For me, it’s the airport. Any airport.

As a traveling sales professional for over twenty years of my career, I spent a lot of time in airports. Three or more days a week for several weeks each month. With my love of spreadsheets, I maintained one for almost fifteen years, tracking the weekly cost of my expense reports. On the day of my retirement, I hit the total button and was amazed, yet a little saddened, to see the result. I had incurred over $750,000 in company expenses, the majority of which was spent traveling to and through airports.

I should be comfortable in airports. They were like a second home to me for over twenty years. So why do airports rattle me now, in my retirement?

It’s not the typical stress of delayed flights, missed connections, and lousy food. The few times a year that we fly now, time is rarely an issue. I schedule comfortable layovers, and usually, we arrive at our destination without significant issues.

The problem for me is rooted in memories of a career that is long past, feelings of invisibility, and the realization of my slow and steady march toward mortality.

Whenever I walk through an airport now, without fail, Leon Russell's iconic song, "Stranger in a Strange Land," echoes in my mind. I muse about my loss of place and relevance in this ever-evolving business landscape. This airport is not my home any longer. I gave up the lease many years ago. I think to myself that I don’t belong here. I am the proverbial stranger in a strange land.

The lyrics of Leon’s song speak of a journey of self-discovery and navigating unfamiliar territory. The first verse pretty much says it all for me: "How many days has it been since I was born? How many days until I die?" Sentiments that resonate deeply within me as I stand among a sea of business travelers, a ghost of the traveler, and, more importantly, the person I used to be.

The Cost of Boarding or the Work-Family Tradeoff

Progress in our work lives, no matter the field, often comes with a cost. It’s not always obvious at first, and the bill rarely arrives all at once. But over time, it adds up, like a credit card balance where you only make the minimum monthly payment. The tradeoffs appear in long hours, missed family dinners, late-night responsibilities, and early-morning alarms.

We sign up willingly, often proudly, in pursuit of growth, status, and providing for the people we love. However, the cost continues to rise until one day, you can no longer afford the minimum payment. The bill always comes due.

When I look back, I see more than a professional life filled with accomplishments and travel miles. I see the cost of those choices. Not in money, but in moments missed. Moments I will never get back. Before I go any further, let me state one point clearly.

I would never pretend that missing a few of my boys’ games or bedtimes compares to the impossible decisions many women face about managing careers and motherhood. That’s an issue with which our society still struggles and there is no perfect solution at hand. It’s also a topic on which I, for obvious reasons, have no personal or moral authority to write.

I do know, however, what it feels like to be caught between professional obligations and the people you love most. I know the sting of watching family life unfold from hotel rooms and airport gates and realizing too late that presence isn’t measured in paychecks and promotions. We are supposed to be there for our kids, for both the good times and the hard ones too. And yet, sometimes, work and career get in the way.

I was sitting on the floor at a crowded O’Hare gate, always O’Hare, half-eaten meal in one hand, phone in the other, flight delayed for the third time that day. The kind of travel day that blurs into all the others. I was checking emails, glancing at the departure board, doing everything I could to pass the time and feel somewhat productive. And then the phone rang.

It wasn’t my wife. It was another parent. His voice was flat, almost stunned. A teammate and close friend of both our sons had been struck by a ball during a lacrosse game. He hadn’t made it. Just like that, one moment of unspeakable tragedy. I was 600 miles away, surrounded by strangers and fluorescent lighting, with nothing useful to offer but silence and an aching helplessness.

I remember pressing my back against the wall of that terminal, watching travelers rush by while I stood utterly still, physically present, yet emotionally absent. There was no way to fix it from there. No way to comfort my sons, or my wife, or even myself. All I could do was wait for the next available flight and hope to make it home before the night was over.

I did, eventually. I arrived late, after the sun had set, and found the neighbors and teammates already gathered in our living room, their voices hushed, the shock still settling in. I stood there, suitcase still in hand, trying to enter a moment that had already moved on without me.

I have no memory of the deal I was chasing on that trip. Couldn’t tell you the client, the meeting, or the pitch. But I will never forget not being there when my family needed me the most.

It’s only with time and distance, both in retirement and life, that I’ve come to understand just how consuming work can be. How it conditions you to believe that everything is urgent and nothing can wait. But the things that genuinely couldn’t wait weren’t found in a workshop, a staff meeting, or a forecast. They were at home. And I missed them.

In my career, I often felt indispensable to my clients. But that night, I was invisible where I most needed to be seen: by my wife, by my boys, and by myself.

From that moment on, I made a deal with myself, perhaps more of a devil’s bargain. I was first in line to get athletic and academic schedules for the upcoming season and semester. I religiously added those events, including family obligations, to my work calendar. I told myself that if I could make and be physically and emotionally present for at least fifty percent of those events, then I could call myself a good father and husband.

I held up my end of the bargain. But did it make up for what I missed?

I still wince a little when I hear Harry Chapin’s Cat’s in the Cradle, especially the line, “When you comin’ home, Dad? I don’t know when, but we’ll get together then.” That song haunted the background of my working life, and, honestly, it still echoes sometimes in my retirement. My boys are grown now. Good men, healthy and well-adjusted, raising families of their own.

They’ve got their own calendars to juggle and their own tradeoffs to navigate. But they didn’t grow up to be just like me, and maybe, for “Traveling Dan,” that’s the most honest kind of success I could have hoped for in return.

I’ve been retired for years now, and the weekly travel is a thing of the past. The suitcase has dust on it, and the airline status has expired. But the echoes haven’t faded. Not all of them, anyway. There are still places that bring it all back. Still moments that take me right to the edge of what was and ask me to look deeply at what remains.

Airports are one of those places. Especially O’Hare.

Years have passed since that late-night call on the concourse floor, but every time I walk through that terminal, something stirs. The lights, the gates, the way people move with purpose. It’s as if my body remembers, even when my calendar no longer requires it.

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If you want to read the entire chapter, you can view it here.

Excerpt from Working Draft of Retired Reflecting and Still Becoming_Chapter 6_July 2025.pd

Download PD • 208KB

Thanks for sticking with me and for making this blog such a meaningful part of my Second Act. I’ll be back soon with more updates, stories, and hopefully a finished manuscript (famous last words) in the not-too-distant future.

If I am being honest, I write a lot like I learn to play pickleball…slowly and methodically.

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.