I was 19 years old when I found myself in a room I had no business being in.
My boss had organized a private leadership retreat, bringing together a remarkable collection of founders, entrepreneurs, and organizational leaders from across sectors. Many of them were people I had admired from a distance. People whose work had shaped my understanding of what it meant to do something meaningful with your life.
There were leaders from organizations like To Write Love on Her Arms, Invisible Children, and HOPE International. People who had built movements, challenged conventional thinking, and invited thousands of others to believe that the world could be different.
At 19, these people were my heroes.
And suddenly, I was sitting across the table from them.
I remember feeling two things simultaneously: immense inspiration and an almost paralyzing sense of imposter syndrome.
I was the young guy in the room. I hadn’t built anything. I hadn’t led anyone through a crisis. I hadn’t experienced the weight of payroll, organizational politics, or the consequences of a decision that affected dozens or hundreds of people.
I was just grateful to be there.
But what I remember most wasn’t the accomplishments of the people in that room.
It was their vulnerability.
Behind every organization was a human being trying to figure things out.
Some of these movements had started almost accidentally. Someone had encountered an injustice, recognized a need, or simply decided something ought to exist that didn’t. They took a step, and then another, and somewhere along the way, a movement emerged.
Others were a decade or more into their work. They had teams, infrastructure, budgets, boards, and reputations to steward. They had experienced the intoxicating momentum of growth and the sobering reality of organizational complexity.
And yet, despite their different circumstances, I remember a common thread running through their stories.
They were deeply convicted about their missions, but not always confident in themselves.
They believed in the work. They believed in the people they served. They believed the world needed what they were building.
But that conviction didn’t exempt them from doubt.
Or fatigue.
Or the uncomfortable reality that leading something meaningful often requires more of you than you think you have to give.
I didn’t fully understand it then.
I think I’m beginning to understand it now.
The confidence myth
There’s a peculiar mythology surrounding leadership.
We tend to tell the stories of founders and executives in retrospect, once the uncertainty has been edited out.
We connect the dots backward, making the decisions seem more deliberate, the vision more obvious, and the leader more confident than they probably were at the time.
What began as an experiment becomes a strategy. What felt like a desperate pivot becomes a defining moment. What was once a fragile conviction becomes an inevitable success story.
And the person at the center of it all becomes something of a caricature: the visionary who knew exactly where they were going.
But that wasn’t what I saw at 19.
And it hasn’t been my experience since.
I’ve come to believe that conviction and confidence are two very different things.
Confidence says, I know I can do this.
Conviction says, I believe this needs to be done.
Sometimes those two things coexist beautifully.
Often, they don’t.
And perhaps one of the more difficult lessons of leadership is learning to move forward when conviction is all you have.
Building something you believe in
Looking back, I think that retreat helped pave the way for Whiteboard, the company I'd go on to found.
Not because I left with a business plan or some grand entrepreneurial ambition.
But because I had been given permission to see leadership differently.
The people I admired weren’t superheroes. They were human beings who cared deeply about something and had chosen to take responsibility for it.
They were figuring things out in real time.
And maybe that meant I could, too.
Years later, building Whiteboard, I found myself returning to that lesson over and over again.
There were seasons when our vision felt impossibly clear and our path forward felt anything but.
There were moments when I felt completely energized by what we were building, followed almost immediately by moments when I wondered whether I was the right person to lead it.
I learned that loving the work doesn’t always make the work easier.
That a meaningful mission doesn’t eliminate organizational complexity.
That building a company you believe in can be both a tremendous privilege and an extraordinary weight.
And that sometimes the thing you’re most proud of building can become the very thing that tests you most deeply.
Entrepreneurship has a way of exposing the distance between the leader you aspire to be and the person you actually are.
I suspect that’s true of most forms of leadership.
But somewhere in that distance is where the real work happens.
The weight of believing
Now, in this new chapter with RKD, I’ve been thinking about that room again.
I’m surrounded by leaders who have spent years, sometimes decades, giving themselves to organizations, people, and missions they care deeply about.
People who have built remarkable things.
People who have carried responsibilities that aren’t always visible from the outside.
People who still believe in the work, even when the work has taken more from them than they anticipated.
And I’ve noticed something.
Most leaders I know carry conviction and exhaustion at the same time.
They aren’t mutually exclusive.
In fact, I wonder if they often travel together.
The people who care most deeply about their work are frequently the people who struggle most to set it down.
They see what’s possible, which makes it difficult to ignore what’s unfinished.
They feel responsible for the people around them, which makes it difficult to separate their own well-being from the health of the organization.
They believe the mission matters, which can make even necessary limitations feel like personal failures.
There’s something beautiful about that kind of commitment.
And something dangerous about it, too.
Because conviction without perspective can become obsession.
Responsibility without boundaries can become resentment.
And a mission that once gave you life can quietly begin consuming it.
I’ve experienced enough of that tension to know that exhaustion isn’t necessarily evidence of meaningful work. Sometimes it’s evidence that something needs to change.
The challenge isn’t simply to keep believing.
It’s to learn how to carry that belief in a way that is sustainable, generous, and shared.
Dreaming in the same direction
One of the things that excites me most about this chapter at RKD Group is the opportunity to imagine what becomes possible when people with deep conviction begin dreaming in the same direction.
Not because everyone has the answers.
Not because we’re free from uncertainty.
And certainly not because the work ahead will be easy.
But because there’s something powerful about bringing together people who have spent their lives believing in the possibility of a more generous world.
People who understand that meaningful change rarely happens in isolation.
People who have experienced both the joy and the cost of building something that matters.
Maybe this next chapter is an opportunity to rethink what leadership can look like when the burden of believing doesn’t have to rest on any one person’s shoulders.
When ambition is shared.
When vulnerability is welcomed.
When the future is something we get to imagine together rather than something one person is expected to predict.
I’ve been thinking about how much of leadership is framed around having a compelling vision.
And vision matters, of course.
But perhaps equally important is the ability to create an environment where other people can bring their conviction, their questions, their experiences, and even their exhaustion into the room.
Where we can be honest about what we don’t know without losing sight of what we believe.
Where we can challenge one another without competing for certainty.
Where we can dream bigger precisely because we don’t have to carry the dream alone.
That’s the kind of leadership I want to practice.
And the kind of organization I want to help build.
Still the young guy in the room
I sometimes wish I could go back and sit beside my 19-year-old self at that retreat.
I’d tell him to listen carefully.
Not just to the stories of success, but to the moments when someone’s voice changes as they describe what the work has cost them.
I’d tell him that the vulnerability he’s witnessing isn’t a contradiction of their leadership.
It’s part of what makes their leadership worth learning from.
I’d tell him that he'll never reach some magical point where the uncertainty disappears.
That building something meaningful will ask more of him than he expects.
That he’ll make mistakes. That he’ll get tired. That he’ll sometimes confuse his own identity with the health of the thing he’s building.
But I’d also tell him that the privilege of building alongside people who believe deeply in something is worth protecting.
And that the greatest opportunities of his life may come not from having a clearer vision than everyone else, but from finding people willing to pursue a shared one.
I’m no longer 19.
I’ve had the privilege of building a company, leading teams, learning from extraordinary people, and beginning a new chapter I couldn’t have imagined all those years ago.
But in many ways, I still feel like that young guy in the room.
Still inspired.
Still learning.
Still occasionally wondering whether I belong at the table.
And still convinced that the work matters.
Maybe that’s enough to keep going.
Not with the confidence that we know exactly what the future holds.
But with the conviction that it’s worth building together.
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