The Founder's Dilemma

... knowing when to let go

This post has been sitting in my drafts—both in my head and my notes—for a long time. Maybe because I've seen this story unfold up close. Maybe because, like many of you, I've wrestled with my own identity shifts in leadership.

But mostly because it's one of the hardest, most unspoken dilemmas in leadership today. We tell ourselves that leadership is about vision, decision-making, and execution. That the best leaders scale companies, raise capital, and build legacies.

But here's the uncomfortable truth:

Leadership is also about knowing when to leave.

And almost no one talks about that part.

The Silent Crisis of Successful Founders

You've probably read "What Got You Here Won't Get You There" by Marshall Goldsmith. There's also a version for women—"How Women Rise" by Sally Helgesen. It's a powerful book about how the very strengths that drive early career success become weaknesses at the top.

But what happens when "the top" comes sooner than expected?

Leadership isn't a slow climb anymore. The old rules—where you spent decades rising through the ranks—are dead. Today's CEOs are founders in their 20s, investors in their 30s, and legends by 40.

And that's exactly where the problem begins. Because if your entire identity is built around being the leader, what happens when the company doesn't need you anymore?

Ryan Petersen's Choice—And Why It Matters

A few years ago, Ryan Petersen stepped down as CEO of Flexport, handing the reins to a seasoned industry leader, Dave Clark. It looked like a textbook case of founder maturity. A strategic, thoughtful transition. A leader making himself unnecessary.

But then, something snapped.

Ryan fired Dave and reinstated himself—in a move that wasn't about strategy, but about something far more human. This wasn't about execution. It was about identity. A realisation that life at the centre of his universe had moved on without him.

Why This Moment is Brutally Personal for Every Leader

It's not just Ryan.

It's every founder who's built something from nothing. Every leader who's poured their identity into a company, a mission, a team—only to wake up one day and realize they are no longer essential.

And let's be honest. That realisation isn't just difficult. It's existential. Because stepping away doesn't feel like a choice. It feels like disappearing.

I've seen this happen. I've felt it. And I know why so many leaders resist this moment—why they hold on when they should let go. Because we don't talk about what comes after.

We glorify the fight—but we don't prepare leaders for the silence that follows when their name is no longer on every decision. We teach them how to scale, but not how to exit. We praise their growth, but not their graceful departure.

And that's why so many leaders make the wrong choice.

I learned this lesson firsthand in a way I never expected. Years ago, within weeks of stepping into a new role leading a distributed ops team, I found myself in a leadership vacuum. My entire senior team was quietly serving notice when I started, the promised tech automation wasn't built, and I was juggling three different managers while racing against a six-month deadline to prevent operational collapse.

Oh, and I was still recovering from childbirth, and was new in the country.

What followed was three months of intense rebuilding—hiring, training, and restructuring while simultaneously handling the workload of six people. When we successfully navigated peak season, it would have been easy to rest on those laurels. To hold onto the identity I'd forged through that crucible.

Instead, I did something that felt counterintuitive: I deliberately made myself unnecessary. I built systems, empowered my team, and automated processes until my presence wasn't critical anymore. And then I left.

Looking back, it wasn't the crisis management or the successful turnaround that I'm most proud of—it's having the courage to make myself redundant.

The Real Test of Leadership Isn't Scaling—It's Letting Go

Every great leader faces this moment. Some step away with clarity, knowing they've built something bigger than themselves. They recognize, as I did, that true leadership success isn't measured by how long you stay, but by how well the system runs without you.

Others—most—reach back, unable to let go.

The problem?

We still equate leadership with control. We think the best leaders never leave. That they are the company. And that belief—not strategy, not performance—is what makes stepping away so brutally difficult.

What If We Changed the Narrative?

What if we treated this moment—not as a failure, but as the final test of great leadership?

What if we stopped glorifying the founder who stays on forever and started celebrating the one who designs their own irrelevance? I've lived both sides of this equation—the adrenaline rush of building something from crisis, and the quiet pride of walking away when it no longer needed me.

Because the greatest leaders don't just build companies. They build ecosystems.

Self-sustaining environments where success is not dependent on a single individual. Where processes run smoothly, teams operate independently, and systems scale automatically. Where the leader's ultimate job is not to be indispensable—but to be unnecessary.

And that's the hardest leadership lesson of all.

The Hardest Question Every Founder Will Face

At some point, every leader will stand at this crossroads. And when that moment comes, the real question isn't:

"Does the company still need me?"

It's much harder than that.

"Who am I without it?"

I've faced that question in the aftermath of both crisis and success. The answer isn't in holding on tighter—it's in learning to let go with purpose. But I’ve seen and worked with leaders who have really struggled to answer that question.

If we don't help leaders answer that, we're failing them.

Not as investors. Not as boards. Not as teams.

But as humans.

Because leadership isn't just about what you build. It's about who you become once you step away. And sometimes, the most powerful thing you can build is your own path to becoming unnecessary.