Sitting in sobriety this week — considering the needs of aging loved ones, my brother-in-law turning 59, looking around the table of my men's group at a few men in their 50s and 60s — and we're heading to Michigan for a funeral, to honor the memory of a man who passed at 70.
Yeah. All the strategy in the world comes to a halt when life happens.
Today, I have my grandfather's timeless words reverberating in my soul from Psalm 90: “Teach us to number our days, that we may gain a heart of wisdom.” I’m not quite in the full Ecclesiastical mindset, calling out “Vanity, vanity” — but in my sobriety, I am pausing long and hard in my fifties to ask some significant questions.
Traveling to Tulsa, I spent time with my longtime friend and mentor, Dr. Nathan Baxter, who has taught me a thing or two about coaching leaders. As our conversation unfolded over salads in 70-degree weather under his back patio, we turned to that old yet familiar concept popularized by Dr. Bobby Clinton in his landmark study The Making of a Leader — Convergence.
Nathan brilliantly affirmed and vision-casted what a focused fifties could look like — and how it sets the stage for thriving in your sixties and finishing well. He named three keys: Margin, Influence, and Intentionality.
1. Margin: The Freedom to Actually Live
Margin is the white space of your life — the unhurried room to breathe, to give, to pivot, to show up. Nathan’s peer group is men in their early sixties, and many are running hard with no end in sight: 45-plus hours a week, no passive income built, still trading time for every dollar. They’ve arrived at a new chapter with no bandwidth to enjoy it.
The danger of living without margin is subtle but devastating. It’s not just exhaustion — it’s the missed grandchild, the friend who needed you present, the inner voice you never had time to hear. The fifties, Nathan reminded me, are your premium earning decade. Your health is still strong, your kids are mostly launched, and you finally know who you are and who you are not. This is the decade to structure well, build passive income, and protect the space that lets generosity actually flow.
Without margin in your sixties, the freedom you worked toward becomes the very thing that eludes you.
2. Influence: Someone Has to Want to Sit With You
Nathan put it plainly: some men have plenty of margin but no influence. Nobody wants to sit down with them. They’ve spent decades distracted, self-absorbed, or hardened by the world’s grinding demands — and now, in the second half of life when wisdom should be most potent, no one is leaning in to receive it.
Influence is built over decades of showing up, being curious, staying humble, and staying invested in other people’s growth. The older you get, the more you want people to listen to you — but that audience is earned, not assumed. The fifties are the season to examine your relational posture: Are you someone people want more of? Do people leave conversations with you more alive, more hopeful, more equipped?
The man with margin but no influence has freedom with nowhere meaningful to point it.
3. Intentionality: Don’t Just Check Out
Nathan gestured toward a recurring image in his week: the same faces at the golf club, every single day. Men who have decided they’ve earned the right to disengage. And in one sense, they have. But in another, they’ve confused the reward of the journey with the end of the journey itself.
Bobby Clinton’s research on why men don’t finish well identifies this checking-out as one of the central reasons for an unfinished life. Men plateau not because they run out of capacity, but because they stop investing in the kingdom, stop leveraging the gifts and experience God spent decades building in them. Intentionality in your fifties means refusing to coast. It means asking hard, holy questions: What am I still being called to? Who am I being called to pour into? What does faithful stewardship of my remaining decades actually look like?
Without intentionality, margin becomes leisure and influence becomes nostalgia.
Every Day Is a Gift
My grandfather’s charge keeps returning to me. Psalm 90 is Moses’ prayer — the oldest in the Psalter — and it is breathtaking in its sobriety. Seventy years, maybe eighty. A watch in the night. Grass that flourishes in the morning and fades by evening. And then the pivot: “So teach us to number our days, that we may gain a heart of wisdom.”
Not to count our days in dread, but to number them — to treat each one as the non-renewable, unrepeatable gift that it is. Moses understood what so many of us learn too late: awareness of limits is not defeat. It is the very thing that sharpens our aim, deepens our gratitude, and produces the kind of wisdom that only comes when we stop pretending time is infinite.
Nathan reminded me: the fifties are not a holding pattern. They are the premium decade for output — the decade where everything you’ve learned, suffered, built, and become can now converge into its most focused, fruitful expression. Build the margin. Cultivate the influence. Live with fierce intentionality.
The sixties are coming. The question is not whether you’ll arrive — it’s what you’ll bring with you when you do.
So yes, today is a gift. Number it. Use it to Love and Live Well! Thank God for the gift of today!
