Climbing the Second Mountain: Finding Purpose Beyond the Family Business
In family business transitions, the hardest part isn’t the legal documents, the succession plans, or even the financial handoff. It’s something far less tangible—and far more personal.
It’s identity.
At the 2025 Bridgeforth Family Business Forum, family business advisor Lance Woodbury spoke to this challenge with clarity: “If people don’t have something to grab hold of, they tend not to let go.” That simple truth gets to the heart of what holds many transitions back. The real issue isn’t just about what comes next for the business—it’s about what comes next for the person who’s stepping away.
The Real Reason Transitions Get Stuck
When a business-owning parent or leader hesitates to pass the baton, they often give surface-level reasons:
“I’m not sure the next generation is ready.”
“I still need the income.”
“There’s too much uncertainty in the market.”
While those concerns may be valid, they often mask something deeper. What many leaders are really wrestling with is a fear of irrelevance. For people who have been the cornerstone of the business, especially in industries like agriculture, stepping back doesn’t just feel like a job change—it feels like an identity crisis.
Who am I if I’m no longer the farmer, the CEO, the one everyone comes to for decisions?
Introducing the Second Mountain
Lance shared a concept from author David Brooks that resonates with many family business leaders: the idea of the second mountain.
The first mountain is all about success—building a business, accumulating assets, expanding acres, increasing impact. It’s where most of us spend our careers.
The second mountain is about significance. It’s what we do with our experience, influence, and time once we step away from daily operations. It’s mentorship, service, creativity, legacy.
For some, it’s as tangible as serving on nonprofit boards or teaching others what they’ve learned. For others, it’s more personal: spiritual growth, building community, writing down the story of the family business for the next generation.
Whatever it looks like, the second mountain gives leaders something meaningful to climb—so they’re not just stepping down, they’re stepping toward.
It’s Not About Golf (Though It Can Be)
When the topic of retirement comes up, conversations often turn to hobbies. “Do you like to fish? Golf? Travel?”
But the second mountain goes deeper than that. It’s not just about filling your calendar—it’s about feeding your purpose.
Jimmy Carter, whose presidency was just the first act of his public life, spent decades building homes with Habitat for Humanity, mentoring others, and teaching Bible study every Sunday until nearly age 100. His second mountain arguably had a greater impact than his first.
Not everyone needs a global platform. But the principle applies: purpose matters. And it’s never too early—or too late—to define it.
The Cost of Not Letting Go
Staying on the summit of the first mountain for too long can have unintended consequences. As Lance put it, “The summit gets crowded.” If the senior generation doesn’t step aside, the next generation may decide to climb elsewhere.
We’ve seen it happen. A son or daughter in their 30s or 40s watches a parent push off retirement again and again. Eventually, they decide not to wait. They seek leadership, ownership, or opportunity elsewhere—not because they don’t love the business, but because the path forward isn’t clear.
If you are a senior leader in your family business, ask yourself: Am I creating room for the next generation to grow, or am I unintentionally blocking their climb?
Peer Groups and Purpose
One way to begin your second mountain journey is to surround yourself with others doing the same. Peer groups—like those facilitated by Pinyon or other leadership organizations—offer a place to wrestle with these questions openly and gain perspective from those who’ve already taken the leap.
Lance also shared research from the long-running Harvard Study of Adult Development: at the end of life, happiness correlates not with wealth or professional accolades, but with relationships. Who we’ve invested in. Who stands around our bedside. Who we’ve chosen to journey with.
Relationships matter—before, during, and after the transition.
A Legacy Beyond the Business
The most successful transitions we’ve seen at Bridgeforth happen when leaders understand that their legacy isn’t tied only to titles or balance sheets. It’s in the people they’ve raised up, the lives they’ve touched, and the wisdom they’ve passed on.
So if you’re feeling hesitant, stuck, or unsure how to step back—consider this your invitation. Your second mountain is waiting. And it might just be your most meaningful climb yet.
Questions to Consider:
What brings you purpose beyond your role in the business?
How might you invest in others once your daily leadership winds down?
Who can walk alongside you as you define your second mountain?
Let us know if we can help. At Bridgeforth, we’re not just here to guide transitions, we’re here to help families redefine what success and legacy really mean.
