The park bench in Gillette, Wyoming, didn’t advertise itself as a place of revelation. It sat near a walking trail in Dalbey Memorial Park, overlooking a modest lake where fishermen cast lines in the late afternoon light. A small metal sign mounted nearby offered something unexpected: a reminder to breathe, along with a simple pathway to mental health resources. Bill Leighty, seventy-eight at the time and exhausted from the three-day punishing cross-country road trip to Montana, after a series of cancelled flights, a vacation that did not go as planned, and facing another three-day return trip, found himself sitting there longer than he’d planned.
What was supposed to be a fifteen-minute rest stop—a chance to stretch cramped legs on the long haul back to Tulsa from Red Lodge, Montana—stretched into an hour and a half. He and his wife, Bonnie, walked the trails, then sat down. The park’s deliberate tranquility, its thoughtful amenities, the care embedded in those signs about breathing—all of it worked on him in ways he couldn’t quite name. He was tired. His allergies had flared badly enough to put him in bed for a day and a half earlier in the trip. He’d been wrestling for months with a question that felt increasingly urgent: What now?
Now, at eighty, Bill Leighty is frank about the math. After thirty-eight years in residential real estate and a lifetime of self-employment before that, he hadn’t saved enough. Retirement, that promised reprieve, had arrived not as rest but as reckoning. He needed to generate income—not for luxuries, but for security. For his wife. For the possibility of leaving something behind for his children. The stakes felt existential, and the energy required felt inversely proportional to what remained.
So he’d done what builders and creators do: he’d explored options. Blogging. Newsletters. YouTube. Print-on-demand. Affiliate marketing. The digital landscape sprawled before him like an unmapped frontier, and every entrepreneurial guru online insisted on the same thing: Find your niche. But which one? And how do you choose when the clock, as Bill puts it, “ticks louder than you think”?
Sitting in that Wyoming park, something shifted. Not a lightning bolt. Not a eureka moment. Just a gradual sense that he was in the right place at precisely the right time, and that despite the fatigue and confusion, everything might actually be okay.
Bill Leighty was born in Newton, Kansas, in 1945—a war baby raised in Tulsa but shaped by the rhythms of small-town life during summer visits to extended family. His father was a salesman and distributor, a man who valued self-reliance over formal education and modeled entrepreneurship as a way of life. Bill absorbed that ethos early. School never inspired him; he attended the University of Tulsa, where he studied business and journalism, but withdrew shortly before earning his degree. He failed the military induction exam due to back problems. What he had instead was a bone-deep need to contribute, to build, to lead, to start his own business.
He spent four years in the residential painting business, primarily focusing on new construction, hiring crews, building a client base, and managing the company, before transitioning to electrostatic painting of metal furniture and fixtures in 1975.
The business flourished until a downturn in the economy in 1987 led to its demise. Then, at the age of 42, he made a decision that would define the next four decades: he obtained his real estate license, which became his primary occupation for nearly four decades.
The work suited him. Not because it was easy—residential real estate is relentlessly competitive, cyclical, and emotionally demanding—but because it rewarded hustle, relationships, and an eye for value. For thirty-eight years, Bill worked in his trade, guiding families through the largest financial decisions of their lives. He learned to read people, to negotiate with empathy, to manage expectations without crushing hope.
But it was civic engagement that gave Bill a sense of purpose beyond transactions. In 2010, Tulsa’s mayor appointed him to fill an unexpired term on the Tulsa Metropolitan Area Planning Commission (TMAPC). He served an additional term after being appointed by a successor mayor, serving a total of five years.
During this time, he studied development cases, visited sites, and chaired the commission for a year. He also served on the Tulsa Transportation Board, tasked with making recommendations to Tulsa’s mayor and city council. These weren’t ceremonial roles. They were the work of someone who believed in the architecture of community—in smart growth, in new urbanism, in the idea that how we build our cities shapes how we live our lives.
In 2014, Bill founded Smart Growth Tulsa, a nonprofit advocacy organization dedicated to promoting sustainable development. By then, he’d been married to Bonnie for decades. They raised children together. They navigated the oscillations of real estate markets and the unpredictability of self-employment. He took up photography seriously, even maintaining a black-and-white darkroom for ten years while his kids were growing up. He learned to cook with intention, planning meals as creative acts of love and expression. These weren’t hobbies in the dilettante sense; they were practices that grounded him, ways of making meaning through craft.
But none of it prepared him for the disorientation of retirement.
The stillness wasn’t restful; it was vertiginous. I felt like I’d stepped
off a moving train and wasn’t sure where I was.
The silence,” Bill says, when asked what was hardest about stepping away from work. “Not just the absence of tasks or calls, but the deeper kind—the kind where you wonder if the world still sees you as relevant.”
He’d underestimated how tightly his identity was braided with being needed, with producing, with mattering in visible ways. Suddenly, he wasn’t indispensable. The stillness wasn’t restful; it was vertiginous. He felt, he says, like he’d “stepped off a moving train and wasn’t sure where I was.”
There were also practical concerns—real ones. He and Bonnie had lost two close female friends in the past year, both in assisted living, but under starkly different circumstances. One lived in a beautiful, well-appointed facility. The other, with fewer resources, died in a place that felt institutional and cold. The contrast haunted him. It forced a clear-eyed assessment: he regretted not doing more financially to prepare. He carried an urgency now, not born of ambition but of love, the need to ensure that Bonnie, his partner of over fifty years, wouldn’t face that kind of indignity.
So, he began exploring. He read voraciously about online entrepreneurship. He considered every avenue. And he kept returning to the same stubborn question: What can I offer that’s authentically mine?
The 2023 Montana trip—meant to be a reprieve—became instead a crucible. After multiple flight cancellations, they threw their luggage in the car and drove. Three days, two nights on the road, Tulsa to Omaha. Omaha to Rapid City. Rapid City to Red Lodge. The vacation did not go as planned, including an allergy flare-up that put Bill in bed for a day and a half. They were not looking forward to the punishing three-day return road trip.
Then: Gillette. Dalbey Memorial Park. Those benches. Those signs about breathing.
Bill doesn’t remember what he thought, exactly, sitting there. But he remembers what he felt: that the world still contained spaces designed for restoration. That someone had cared enough to put those signs there. That maybe—just maybe—other men his age were sitting on benches in parks across the country, wondering the same thing he was wondering. What now? What’s left? Does any of this still matter?
Maybe—just maybe—other men his age were sitting on benches in parks across the country, wondering the same thing he was wondering. What now? What’s left? Does any of this still matter?
That restful and contemplative moment sustained them the rest of the trip home, which included some unexpected gifts: a visit to the Corn Palace in Mitchell, South Dakota; the fifty-foot Dignity of Earth and Sky statue near Chamberlain; and the Old Market District in Omaha. But it also extracted a toll. Fatigue. Allergies. The weight of uncertainty.
Adding insult to injury, Bill and Bonnie both tested positive for COVID-19 after they reached home in Tulsa, so it was no surprise they were not feeling well.
Nevertheless, the seed was planted and began to bloom.
The Encore Project was launched in 2024. It began as a blog, then expanded into a multi-dimensional platform dedicated to helping senior men navigate what Bill calls “the second half”—the years after career, after the structures that once defined them, after the world stops asking for their labor in obvious ways. The site explores personal growth, faith, creative pursuits, grief, financial literacy, health, technology, and relationships. It’s part resource hub, part storytelling project, and part community.
Bill has written over 450 blog posts, many of them AI-assisted, covering the landscape of concerns he knows firsthand. But he wanted something more irreducibly human. That’s where the “Meet [First Name]” series comes in. These are long-form narrative profiles, built from interviews, designed to show what aging actually looks like when men tell their own stories without sanitizing the complex aspects.
He’s starting with himself. Not out of ego, but because it felt right to go first—to model the vulnerability he’s asking of others.
Bill Leighty still lives in Tulsa with Bonnie, in a high-rise condo with nineteenth-floor balconies where he watches sunrises and sips wine in the evenings while contemplating how to improve The Encore Project’s content and strategies. He still cooks thoughtfully. He still takes photographs, mostly with his iPhone now. He still writes, treating it as a spiritual practice to metabolize experience into understanding.
Every summer, they vacation with family and friends in Montana, almost always flying. Last year, they managed to do it without any cancellations.
When asked what he hopes people remember about him, Bill doesn’t hesitate: “That I cared deeply. That I didn’t give up when it got hard. That I built something meaningful in the face of uncertainty.”
The Encore Project, at its core, is an argument: that older men are not relics but resources. That this chapter of life—messy, uncertain, often lonely—can still be generative. That purpose doesn’t retire, even if you do.
Bill knows the stakes. He knows that financial security remains precarious, that the future is unwritten, that time is finite. But he also knows this: sitting on that bench in Gillette, watching strangers walk trails in a park built for rest, he felt something he hadn’t felt in months. Not certainty. Not ease. But possibility.
That feeling, it turned out, was enough to build on.
Bill Leighty is the founder of The Encore Project, a digital platform dedicated to helping senior men reimagine life’s second half. If you’d like to share your story for the “Meet [First Name]” series, visit The Encore Project website to learn more.
