Until today, I have mostly written about the hidden cost of doing it all. The burnout tax paid by leaders who treat support as a luxury. Today, I’m turning the lens outward: what happens when leaders trade bravado for a team-first culture?
No matter how well you plan, chaos finds you. You line up your puzzle pieces, then just like that, life throws a curveball at you and you find you’re looking at an entirely different puzzle.
My reflex has always been the same. Hold everything together. Project certainty. Look confident even when I had no idea what I was doing. Somehow I’d absorbed that steadiness meant never showing uncertainty. My notion of a leader was antiquated, one full of bravado and strength. But as I have learned the hard way, false bravado burns hot and fast, leaving a culture that models exhaustion instead of resilience in its wake.
We all pay a tax for this. Our poor self-regulation leads to team burnout, bad results, unhappy employees, and dissatisfied customers. It’s the backpack of expectations, packed not just for ourselves but for everyone around us.
But there’s a better way. Sustainable momentum (progress that compounds without burning out the people who create it) requires a team-first culture. In my experience, momentum lasts when leaders stop performing certainty and start creating the conditions for teams to thrive. The trick is to let go of our antiquated models that drain us, in favor of a new model that sustains itself.
Here’s the shift:
I’m a big fan of the podcast Founders, where the host David Senra tells the story of history’s greatest entrepreneurs. If you’ve not listened to any of his episodes, he reads snippets of entrepreneurs’ biographies and pulls out what makes each story so remarkable. Some of my favorite episodes might be surprising – the three on Estée Lauder were particularly wonderful.
Regardless, it has been especially interesting for me to study what other paths leaders have followed in the face of chaos. While many fall into the same trap so many of us continue to fall into, many others find a way to set down their bravado, instead relying on the collective wisdom of those who surround them.
Senra has talked a fair amount about Walt Disney, but I loved this episode. The journey to what would become Disneyland is full of uncertainty and countless rich leadership lessons. Disney’s laser-focused obsessiveness is well known, yet new to me were the systems, rituals, and spaces for imagination. He intentionally crafted spaces and opportunities for collective execution. I imagine his vision was so grand that he knew he couldn’t achieve it alone. Or perhaps he realized how much stronger the end result could be when the collective genius of his team was put to work.
Even before he fully understood his vision, Disney believed play was a requirement. He built a half-mile steam railroad in his backyard. Not as a business venture, but as play. That small, seemingly useless project became the seed of Disneyland: a place where people could step inside a story. I took for granted how novel that idea must have been, but it was truly remarkable.
So as his vision took shape, he took pains to ensure his team would have the best chance of happening on similar seeds of creative genius. He was ambitious, but he ruthlessly prioritized conditions for imagination to thrive. Think about the conditions you need to allow creativity to thrive. Does it involve sitting still behind a screen, or even at a desk, for long stretches of time? Lots of meetings, deadlines, and required outputs? Probably not. It certainly wasn't for Disney’s team.
What I love is that he didn’t aggressively build his dream through force or certainty. He crafted environments where teams could dream, iterate, and be fully human even while under immense pressure. As the park neared opening, the pressure nearly broke him. Banks doubted him; he was over-leveraged, and he often broke into tears. Opening day itself was chaos. Rides broke, asphalt melted, counterfeit tickets overwhelmed their capacity. Instead of hiding his frustration, Disney let his team see it. That vulnerability didn’t weaken trust, it galvanized his team to fix problems one at a time.
He wasn’t trying to inspire. He was simply being human, admitting he wasn’t sure it would work. That vulnerability, paired with grit and play, turned Disneyland into what it is today.
After listening to many episodes, there seem to be a few ever-present themes.
True leadership isn’t bravado. It comes from cultivating structures that let the collective shine. Surround yourself with people who stretch you. Create conditions instead of answers. Lead with honesty instead of certainty. That’s how you trade bravado for momentum that lasts. Just as we learn to put down our own backpacks, it’s time to stop packing our team’s bags with unnecessary burdens.
What’s one problem you could name and share with your team this week?
What’s one uncertainty you could model openly?