“Midlife is a time for moving from a life of ambition to a life of meaning…away from the relentless pursuit of external rewards and toward a focus on relationships, contribution, and inner peace.”
-Arthur Brooks, From Strength to Strength: Finding Success, Happiness, and Deep Purpose in the Second Half of Life
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In midlife, we’re often said to be entering a new chapter—a “second phase” of life. With that comes a wave of stereotypes about what success and winning should look like. But success can—and should—mean whatever we want it to.
It’s not limited to middle age; it’s a moving target, evolving as we do. In my 20s, success was one thing; in my 30s and 40s, it transformed into something entirely different. Now, in my 50s, I’m focused on slowing down in some areas while accelerating in others. My priorities have shifted, but the drive to live meaningfully is only growing. Years of work have gone into preparing for this next chapter—into figuring out how to really live in it, not just coast through.
For me, this transition has meant designing my life rather than defaulting to it—making conscious choices to shape my days around what I value most.
It’s about building a life that feels so fulfilling I’d do it for free, not one driven purely by the grind for financial gain.
Rather than searching for purpose or passion outside of my work, I’ve created a life where those things are woven into everything I do.
Case in point, this week we’re revisiting our interview with Troy Aikman. Why? Because there’s more to his story that we didn’t capture the first time.
It was our inaugural issue of Midlife Male, and we, too, want to improve with age. Here we are at Issue 14, aiming to bring you our best work.
Athletes like Troy are uniquely familiar with the “next chapter”—they face it much earlier than most of us. Their careers tend to be short, with few making it into middle age. But with breakthroughs in health and longevity, some are defying those limits—Tom Brady, LeBron James, Laird Hamilton, Kelly Slater. That’s a topic for another day.
The question is, what comes after such a singular pursuit of winning? For some, moving beyond that first identity is nearly impossible. But Troy’s story is different. He’s expanded his life beyond football to broadcasting, investing, and entrepreneurship, bringing the same intensity to each new venture.
His journey reflects a potential we all share. He’s prioritized health and discipline, becoming stronger in midlife than in his early career. He’s found meaning in winning off the field, in life itself—an ethos that lies at the heart of Midlife Male.
This journey is about redefining “winning” with each chapter of life. It’s a flexible, evolving framework that we adjust as we go. Our 6Fs—family, fitness, finance, food, fashion, and fun—may not look the same for everyone, but they offer a structure. They remind us that winning isn’t static; it’s a conscious effort to focus on what truly matters, investing in ways that resonate deeply at every stage.
