A question of legacy, part one: Two paths after 50

Jun 27, 2025  |  

A question of legacy

My father died suddenly back in 2003. His passing wasn’t a total surprise. He was 75 and in failing health. The memory that endures is ending the conversation because I needed to do some late-night work. No big deal. I knew we’d talk in the next day or so.

Except we never did.

A few weeks ago, I stumbled across my notes for his eulogy. My memory of looking out across the packed church and thinking “people really loved him” is clearer than my memory of what I ate for breakfast three hours ago. In the receiving line, I kept hearing his was a “life well lived.”

Those memories came flooding back as I sat down to write this article and realized he passed exactly 22 years ago. It was one of those goosebump moments and threw me off more than the photo of him on my bookshelf ever does. And it left me wondering if my family would hear the same thing if it happened to me.

I’ve been writing on this platform about my journey back to joy. The pursuit of joy inevitably leads to questions about legacy.

Here’s the crossroads many of us face after 50: Do you want your legacy to be defined by how your co-workers remember you? Or do you want your legacy to be defined by how true you’ve been to yourself and your values? It’s not just an academic question. It’s the difference between chasing what impresses others and pursuing what genuinely matters to you.

Family road trips in the late 1960s were seatbelt-free and loud.

My father’s legacy and the lessons between the lines

His obituary said he “dashed off occasional humor pieces for The Buffalo News,” and while it did highlight his career as a PR executive, it focused more on his view that one’s automobiles symbolize “life’s passing parade,” on his broadcast of a world championship boxing match from Tokyo for the Far East Network of Armed Forces Radio during the Korean War, on his volunteer work for Radio Reading Service and Meals on Wheels, and on his love for bridge, big-band music, and jazz. And he was a diehard Buffalo Bills and Syracuse University sports fan – and lived just long enough to see the Orange basketball team win the National Championship.

It was a legacy of “small” moments — of long drives to Maine sitting in the backward facing part of a station wagon with no seatbelts and an irritating younger sister, of his endless fretting about whether sports leads were safe until the final buzzer, of my always feeling loved. I do remember the phone calls in the middle of the night from the Niagara Mohawk “Trouble Office” about power outages, but the job never defined him. In retrospect, my eulogy echoed that legacy, but I don’t think I fully embrace it beyond coaching my kids in their various sports and trying to be consistently “present” for big and small moments.

Dad took me to a Bills game for my birthday at War Memorial Stadium and didn’t make me leave even though it was pouring throughout a 43-0 beatdown.

Two paths diverge in midlife

Many of us spend decades building the résumé version of our lives filled with career achievements, recognition and professional impact. That’s the stuff you publish on LinkedIn or include in a conference speaker introduction. This path has value; we need people who strive to excel and improve their workplaces and subordinates’ potential.

But there’s another type of legacy that emerges in midlife: legacy as authenticity. This isn’t so much about funeral eulogies as it is about what you’ll know in your quiet moments of reflection. Did you live courageously? Were you true to your values? Did you nurture important relationships and speak your truth, even when it wasn’t popular?

Research shows people over 50 report higher levels of life satisfaction than those in their 30s and 40s. The fog lifts. Our vision – the kind that matters – becomes clearer.

Perhaps most telling is what palliative nurse Bronnie Ware discovered while caring for the dying. The most common regret she heard was, “I wish I’d had the courage to live a life true to myself, not the life others expected of me.”

The journey continues

Understanding these two paths is one thing. Living them is another.

In the second part of “A Question of Legacy,” I’ll share how a recent project helped me discover which path truly matters and how you might find your own answer.

Keep any eye out for the follow up early next week.

Thanks for joining me on the journey.

Peter Osborne shares why legacy becomes personal after the age of 50.

"Life is a choice. It is your life. Choose consciously, choose wisely, choose honestly. Choose happiness."

Bronnie Ware

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