Having Real Friends in Midlife—and Other Miracles
The last year of my life and the remarkable men I've gotten to spend it with.
On a recent Sunday, my wife and I sat in church listening to a sermon on the miracles of Jesus.
The pastor listed them off — turning water into wine, walking on water, healing the blind, raising Lazarus from the dead. Then he paused before sharing what he called the greatest miracle of all.
With a smile, he said, “Jesus had twelve friends in His thirties.”
The room laughed — a mix of amusement and knowing discomfort. Because beneath the humor was a truth many of us feel, especially men, especially those in leadership or public life.
Real friendship doesn’t always come easy in adulthood. When your life revolves around what you do instead of who you are, it can be hard to know who’s really walking with you and who would still want to be your friend if you lost your mojo.
Vulnerability feels risky. Sharing your struggles might make you look weak. Sharing your hopes might make you seem naive. And so, too often, we keep things to ourselves.
I’ve felt that. Maybe you have, too.
At the end of 2023, during a transitional season for my wife and me, our friend Donald Miller invited me over to his place. He told me he had “a wonderful plan for my life,” and if I was willing to hear it, he’d share it. I figured anything with the word wonderful in it was worth listening to.
As we talked, Don shared a concern that had been growing in him — a deep awareness of the hidden loneliness and isolation that so often shadows men in leadership. From the outside, leaders look connected. Surrounded. Resourced. But on the inside, many wrestle with an ache few people ever see. It’s hard to know who you can trust. Hard to name your fears. Harder still to name your longings.
Then Don asked a question that got my attention: “Scott, what if your next thing wasn’t about serving thousands, but about walking more deeply with a few? What if you created a space not for networking, but for connection? A place of coaching, encouragement, and focused pastoral support for leaders who carry much but rarely have a place to lay it down?”
I didn’t know what to say. I told Don I wasn’t sure I was ready for something like that. But he gently suggested a next step: gather a few trusted friends and ask them what they thought.
So we did.
To my surprise, every single one affirmed the idea. Then they asked if they could be part of it. So, still unsure how it would all unfold, I said yes to those six men. And then, within a few short months, a community for leaders who want to integrate faith with all of life — personal, at home, at work, in friendship and community — was born.
We would end up calling it The Sycamore Community — a name inspired by Jesus’s loving pursuit of a man perched in a tree, a rich, accomplished, lonely leader searching for answers. That moment — Zacchaeus in the sycamore — affirms that even those who appear to have it all together are often just trying to catch a glimpse of grace. And when Jesus saw him, He didn’t call him down with judgment, but gave him friendship.
What began as a plan for six soon grew to twelve, then twenty. Then thirty. Eventually, we capped the group at thirty-three — a nod to the number of years Jesus walked the earth, and a reminder that transformation doesn’t usually happen in huge crowds, but it does with a committed and hungry few.
The vision we started with was simple and focused:
To create a space where high-output, high-responsibility leaders could step out of the spotlight and into authentic connection and community.
To foster honest conversations about the things that matter most — faith, integrity, marriage, parenting, friendship, and vocational calling.
To offer a rhythm of teaching and discipleship, encouragement, connection, and truth-telling, grounded not in performance but in grace.
To become a brotherhood marked by trust, honesty, and mutual sharpening.
We would not gather around a platform or a stage. Instead, our space would be a table. And around that table, the hope was that men who lead others might find an oasis in which to be led themselves — by the wisdom of grace, by Jesus, and by each other.
From late August 2024 through early May 2025, the full Sycamore Community gathered once a month at the Miller’s carriage house in Green Hills (pictured above). Each evening began around the table, where our friend Kate (who also took the photos you see here) welcomed us with a meal that felt like a foretaste of the New Heaven and New Earth. Kate’s gift for hospitality — equal parts culinary brilliance and heartfelt warmth — set the tone for everything that followed.
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After the meal, we would turn our attention to the deeper work: with teaching, guided conversation, and occasional featured guests around a central theme for the month. The goal, over time, was to guide each participant — slowly and intentionally — toward writing his own eulogy, imagining it being delivered by the people who lived closest to him. This wasn’t about anything morbid — it was about vision. What kind of legacy do we hope to leave in the things that matter most: integrity, marriage, parenting, friendship, community, and vocation — all viewed through the lens of faith in Jesus?
In between our larger gatherings, we met in smaller peer groups of six. These more intimate circles gave space for deeper conversations, and over time, trust and deepening connection took root. Strangers and acquaintances became brothers. Real friendships emerged that will no doubt continue for years to come.
Our final gathering came on the evening of May 6. Before Al Andrews — founder of Porter’s Call and a beloved sage to so many in Nashville’s creative community — offered a wise and warmhearted send-off, we opened the floor for sharing. There was no pressure or expectation to share, but still every man did. One by one, each offered his honest, heartfelt gratitude.
One man shared candidly: “I joined Sycamore hoping to grow closer to the friend who invited me. And I did. But what I didn’t expect was this: guys I wasn’t sure about — I now consider brothers that I would take a bullet for.”
Many spoke of healing and transformation. One confessed: “This year, I finally got honest about the idol I’ve made of money. Through the conversations here — and the framework we were given — I started learning to live with more integrity. And with more ease.”
One offered a metaphor that was relatable to nearly everyone in the room: “For most of my life, I’ve tried to be a Redwood — tall, impressive, towering. But now, I want to be an Oak. Deep-rooted. Strong. Quietly faithful. A source of shade for others. Sycamore gave me a map to become that kind of man.”
Some spoke of burnout. Others named the grief, leadership fatigue, or struggles in marriage they first carried into the program.
One said, “You all helped me face the truth — that I was exhausted and deeply unhappy. I was going through the motions. But because of this community, I got help. I’m 20 pounds lighter and spiritually more alive than I’ve been in years.”
Others echoed similar themes:
“If you want to be lonely in this group, you’ll have to fight for it. I’m so grateful to have a place of such deep, authentic connection.”
“At first, I thought I was too busy to do this. But by the end, I realized I was too busy not to do it.”
“Because of Sycamore, my daughter has a better dad.”
“Most of us don’t always feel like we’re the best version of ourselves. But we’re all trying to be. And trying to be those men together has helped us get somewhere.”
Some came to Sycamore in a season of transition. Others arrived hoping for the kind of community that doesn’t just skim the surface. One man said transparently: “I joined Sycamore thinking it would help me build connections in the city for my work. What I didn’t expect was how God would use this group to completely reorder my priorities — and my heart.”
If You Or Someone You Care About Is A Leader…
And now, we’re preparing to do it again.
We’re also making room for a new group of leaders who feel a longing for more. Leaders who are ready to trade the grind for a more intentional, meaningful way of being.
If that sounds like you and you’re from the Nashville area, we’d love to start a conversation about welcoming you into the Sycamore Community.
Learn more or apply here.
As I look back on this past year, I feel gratitude. What began as a friend’s idea has become one of God’s most life-giving surprises. For a short season there, I didn’t have a wonderful plan for my life — but am glad that God did — and put it in the heart of Donald Miller to share it with me.
So here’s to year two.
And here’s to the miracle of having real friends in adulthood.
To learn more about The Sycamore Community, click here.
Going Deeper:
➤ Companion teaching (12 minutes) that expands on this essay’s core themes:
➤ Q&A Response → Based on questions from readers and listeners.
Scott, perfect timing. We don’t live in Nashville area - but please pray my hubbie will somehow find or start or pray to find such a gathering of men. He’s been the lone redwood. And a wanderer/traveler. Thank you. Read this piece just after speaking with him about all the issues you mention. Especially being at a loss as to what’s next. Gracias! ☺️