Anchored Against the Coming Storm, But Not Yet Finished

This past week, the last of 2025, found me coming back to a familiar set of images.

Once again, twenty-foot waves are pounding the eastern shores of Lake Ontario. Gray skies, a staple here in Central New York, and wind howling with gusts exceeding 60 mph. Water smashing into the rock and concrete of the Oswego Harbor Lighthouse with zero interest in whatever is standing in its way.

And like it always does this time of year, my mind goes to Gordon Lightfoot and his haunting song, The Wreck of the Edmund Fitzgerald. I think about a boat without an anchor in this kind of weather. It doesn’t matter how strong the hull is or how experienced the captain might be. Without something holding it in place, the boat drifts, then gets pushed, then tossed around by forces bigger than ever imagined, until the rocks appear or, worse, the bottom of one of these Great Lakes.

Retirement, like open water on a stormy December day, requires an anchor.

That anchor can be a person, a place, or a purpose, sometimes all at once. For me, writing has been a steadying force, a purpose that keeps me grounded as I explore what life looks like beyond job titles and scoreboards. It hasn’t stopped the waves from crashing, but it has kept me from drifting into the rocks.

That brings me to a small milestone I’m finally ready to share after a year of work.

After a lot of early mornings, coffee refills, false starts, rewrites, and quiet walks with Rigby to think things through, the first complete draft of my book on retirement is done. Done as in finished, printed, saved, backed up, and read more times than I care to admit. I’m now deep into the final editing process, sanding down the rough edges, tightening language, and making sure the voice on the page still sounds like The Sunny Side of 57 and me.

Early in 2026, I’ll begin the next phase, deciding how this book gets out into the world. That may include a search for a literary agent and publisher, or I may choose to captain the ship myself and self-publish. Either way, I’m selecting a route to market with intention, not urgency.

Below is a short excerpt from Chapter 8 of the manuscript. It’s from a section that explores why finding your purpose matters so much in retirement, not as a scoreboard, but as an anchor that helps us stay upright when the water gets rough.

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From Scoreboards to Mirrors (Excerpt from Chapter 8)

For most of my life, validation came from outside me. A grade from a teacher, a nod from a boss, a sales target hit or missed. The scoreboard wasn’t just a way to measure performance. It was a way to measure worth. Retirement stripped most of that away.

And that’s when I realized the question isn’t whether the scoreboard disappears. It’s whether you can learn to build one inside yourself. Because eventually, the loud applause of promotions and paychecks gets replaced by a quieter question: Am I living in a way that matters to me?

When one daily routine fades, another can take root. Retirement frees us from chasing numbers and offers the chance to move from external scorecards to internal ones. It’s no longer about proving that you are winning the race. Instead, it’s about knowing, deep down, that you don’t need to win for anyone but yourself.

For me, the best example of this shift has always been my older brother. Though we spent our early years scrapping like typical siblings, I’ve spent the last forty admiring him. He worked for decades in a county agency serving adults with disabilities. It was quiet, meaningful work that gave back to the world. But outside of his job, he built his own kind of scoreboard, one based on joy and curiosity.

I remember when my kids, still young and discovering rock and roll, asked him how many concerts he’d seen. He grabbed a yellow legal pad and began to list them. Joan Jett, Tom Petty, The Stones, Springsteen, and the list went on. By the time he finished, there were over 200 entries, and he paused to ask if “opening acts” should count too. My kids sat in awe.

At the time, it was just a funny family moment. Today, I see it as something more: an internal scoreboard, built not on promotions or paychecks but on experiences that mattered to him.

In retirement, that pattern continues. He keeps lists of the number of Cincinnati Reds games he’s attended each season, books he’s read, laps he swims at the Y, and even the states he’s visited (only two left to go). But what really stands out, for me, is the uncountable: his friendships, his kindness, and his presence in people’s lives.

Watching him, I see a retirement well lived. When his career scoreboard went dark, he didn’t flounder. He simply turned up the one he’d been using all along. And that’s the lesson for me: internal validation doesn’t appear out of nowhere in retirement. It grows from the things you’ve always valued or were curious to explore. You only need to be willing to let them guide you.

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If you’ve already retired, are thinking about it, or are somewhere in between, I’d love to hear from you. What’s your anchor right now? A person, place, project, or something completely different?

Because those waves don’t stop coming, but with the right anchor, you don’t have to drift.

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 aspires to write a new post at least once a month.