I’ve spent most of my working life in elite sport, and one thing I can tell you with certainty is that high performance is never really about the scoreboard. The scoreboard matters, of course. Results matter. Winning matters. But the deeper lessons always sit underneath the result itself. They sit in the complexity of people, the ambiguity of leadership, and the challenge of continuing to show up when things feel uncertain, uncomfortable, or overwhelming.
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That, to me, is what it means to be in the arena.
I’ve often used the metaphor from Theodore Roosevelt’s famous speech about the person whose face is “marred by dust and sweat and blood”. Not the critic standing outside the arena, but the person willing to step into it. Leadership asks that of us. It asks us to willingly place ourselves into environments where there are no guarantees, where fairness is not promised, and where the expectations can feel relentless. But it’s also where the real growth happens.
One of the biggest distinctions I’ve learned over time is the difference between complicated and complex. Complicated problems usually have answers if you work hard enough to uncover them. Complex problems are different. They involve people, emotions, relationships, and dynamics. There often isn’t a clean answer. Leadership exists because of that ambiguity. If everything was certain and predictable, we wouldn’t need leaders at all.
In football, we simplify things down to three expectations. Know your role. Accept your role. Play your role.
Simple to say. Incredibly difficult to live.
People often talk about clarity as though it’s something you can hand to a team. I’ve never experienced it that way. Clarity is an outcome of connection. The more connected a group becomes, the clearer people are about who they are, what matters, and how they contribute. That means leaders have to meet people where they are, not where we wish they were. I learned that the hard way.
I think about someone like Max Gawn at Melbourne. People see confidence when they watch him lead, but confidence is rarely where leadership starts. Most leaders grow into it. Leadership becomes powerful when it’s a full expression of who you are, rather than an imitation of who you think you’re supposed to be.
I certainly learned that lesson painfully.
When I became CEO of Richmond at 24, I thought leadership meant becoming some idealised version of a “great leader”. I borrowed bits and pieces from everyone around me. I tried to sound like other people, think like other people, lead like other people. In the process, I forgot to be myself. The hardest thing to be as a leader is yourself.
Over time, I realised something much simpler. Great leadership is really about being a great learner. Confidence doesn’t come before the experience. Confidence comes from moving through the experience, reflecting on it honestly, and allowing yourself to grow from it.
That growth usually comes through struggle. Sport understands this better than most industries. In elite sport, mistakes and disappointments are not interruptions to growth. They are the growth. Every successful team I’ve been part of has had to endure difficult moments first. Grand finals lost. Public failures. Internal conflict. Periods where nothing seemed to work.
One of my favourite sayings from the Stoics is: what stands in the way becomes the way.
The obstacle often becomes the path forward.
I remember Melbourne being thrashed in a preliminary final years before they eventually won a premiership. In the moment, it felt devastating. But those experiences forced conversations that otherwise never would have happened. They forced honesty, accountability, and ultimately deeper connection.
Leadership asks us to become comfortable with discomfort. Not to enjoy it necessarily, but to stop running from it.
I’ve spoken openly over the years about my own struggles with depression. For a long time, I carried it as a secret. Now I almost see it as a gift because it forced me to go deeper into myself. Leadership eventually demands that depth from all of us. It asks questions of us that can’t be answered with surface-level thinking.
When I feel overwhelmed now, I still go back to a very simple practice. I take out a pen and paper and ask myself: what does this moment expect of me?
Then I write down four words.
Calm.
Brave.
Humble.
Compassionate.
What would a calm leader do now? What would a brave leader do now? What would a humble leader do now? What would a compassionate leader do now?
That process slows the moment down. It creates space between reaction and response. In leadership, velocity is rarely the answer to complexity. Slowing down often is.
I learned that lesson from watching great athletes. The best players somehow make the game feel slower around them. They don’t panic. They don’t rush. They create clarity in chaotic moments.
I also think leadership requires us to continually distinguish between what seems to matter and what truly matters.
The things that seem to matter are loud. Emails. Notifications. Meetings. Performance metrics. External opinions. All the noise competing for our attention.
The things that truly matter are quieter. Trust. Belonging. Connection. Integrity. Self-awareness. The quality of our relationships.
If we understand what truly matters, we’re far more capable of handling what merely seems to matter.
I saw this beautifully in football environments over the years. Some of the strongest cultures I witnessed weren’t built through slogans or strategy documents. They were built through moments of genuine human connection. Players looking after each other. Leaders creating environments where people felt safe enough to contribute honestly. Teams learning to become stronger together.
And that phrase matters to me. Stronger together.
Not stronger individually. Not stronger through hierarchy. Stronger through connection.
I think one of the great responsibilities of leadership is creating the conditions where people understand what we’re trying to achieve and why their contribution matters to it. That’s the real work.
There’s another line I come back to often. If it isn’t happening in you, it won’t happen through you.
Leadership always starts internally. We can’t create trust externally if we don’t have honesty internally. We can’t create courage in others if we continually choose comfort ourselves.
I learned that through my own failures as much as my successes. I was sacked twice as a CEO. Those moments hurt deeply. But with distance and reflection, they also became some of my greatest teachers. They forced me to confront the difference between responsibility and ego. Leadership is all on you, but it’s not about you.
That distinction changes everything.
These days, I spend much of my time coaching leaders, CEOs, and coaches themselves. What I’ve discovered is that the fundamental questions remain remarkably consistent regardless of the industry.
What does the role expect of me?
What do I expect from the role?
What do I expect of myself?
They’re simple questions, but if answered honestly, they can reshape the way we lead.
And perhaps that’s the real invitation of leadership. Not perfection. Not certainty. Just the willingness to keep learning, keep reflecting, and keep stepping back into the arena despite the bruises and disappointments that inevitably come with it.
Because the game does not give up its rewards easily.
But when we embrace the discomfort, stay curious, and remain open to growth, something powerful happens. We stop trying to become somebody else’s version of a leader and start becoming a fuller expression of ourselves.
That’s where leadership begins to feel real.
And if this conversation struck a chord, I’d love to continue it sometime. Maybe over a coffee, maybe at the next Masterclass, or maybe simply through your own quiet reflection with a pen and paper in hand.