The Tallest Building

Today's Read Time: 2.18 minutes

I was listening to a podcast with Gary Vaynerchuk recently when the host asked him about the biggest opportunities he had ever missed. He confessed that he ignored an email from the founder of Airbnb and passed on investing in Uber. Twice. Mistakes that cost him hundreds of millions of dollars.

The host wanted to talk about regret, but Gary had almost no interest in revisiting decisions he could no longer change. Instead, he offered a thought that has stayed with me.

"There are two ways to build the tallest building in the city. You can spend your life building your own, or you can spend your energy tearing everyone else's down."

Over the past several months, I've found myself noticing that philosophy everywhere.

It see it in organizations competing for talent, businesses chasing market share, leaders protecting influence, and conversations where someone else's success is met with criticism instead of curiosity. I don't believe it's bad intention. More likely, I suspect it grows out of a belief that opportunities are limited, attention is scarce, and someone else's momentum must somehow come at our own expense.

The tragedy is that scarcity has a way of whittling away at our character long before it reshapes our results.

Scarcity changes the story we tell ourselves about other people. A colleague's promotion becomes evidence that we were overlooked. A competitor's growth becomes proof that we're falling behind. Someone else's success starts to feel personal, even when it has nothing to do with us. If I can lower your building in my mind, I don't have to confront why mine isn't where I hoped it would be.

I think that's why secure people are remarkably generous.

They celebrate opportunities that don't belong to them. They make introductions without wondering what they'll lose in return. They recommend people who could one day outperform them. They aren't generous because they're less ambitious. They're generous because they're not measuring their own worth against someone else's progress.

The greatest threat to generosity isn't ambition. It's insecurity.

I've spent enough time inside organizations to know that insecurity doesn't always look the way we expect it to. Sometimes it sounds like gossip. Sometimes it's disguised as constructive criticism. Sometimes it shows up as gatekeeping, comparison, or the need to remind everyone why someone else's success isn't quite as impressive as it seems. We justify each moment as insignificant until we look up and realize we've become more committed to protecting our place than contributing to someone else's progress.

I want to build something extraordinary and I'm not trying to hide that. I want Monyok Leadership to continue growing. I hope our work reaches more organizations, serves more leaders, and creates opportunities for our team to do meaningful work for years to come. But I don't believe ambition and generosity are competing values. In fact, I believe the strongest leaders possess both. They build exceptional things while creating space for other people to do the same.

For me, I'm not sure the tallest building was ever the point.

When it's all said and done, I hope my legacy won't be measured by the height of what I've built but instead measured by what still stands because I was here.