This past week, I moved between two very different worlds.
Leadership, Observed
One was hospitality. Rooms full of founders, investors, and operators building brands and re-imagining the future. One conversation stayed with me. We kept returning to the same question:
How do you grow while staying rare?
How do you scale without sliding into sameness?
Then came my stepdaughter’s graduation.
At first they felt unrelated. But they were asking the same question.
The founders I met were betting on an uncertain future and working to build it. The graduates were standing at the edge of an uncertain future too.
What struck me was their confidence.
Many of these young adults have something I did not have at their age: deep roots. Faith. Community. A sense of belonging. You could see how much steadier that foundation made them.
I arrived in this country as a refugee at 17. Confidence was not something I inherited. It was something I built slowly through work, resilience, and the proof that I could land on my feet.
So I have come to think there are different paths to courage.
One comes from knowing you can always land on your feet.
The other comes from knowing someone will always be there to catch you.
The older I get, the more I appreciate the second one.
Watching these graduates cross the stage, I kept thinking about what we are sending this generation into.
It is commencement season. Too many speeches seem focused on telling graduates what to think. Too few focus on teaching them how to think.
One speech stood out. Noah Eckstein’s address at Harvard was not a call to choose a side. It was a call to stay curious. To question your assumptions. To value truth over certainty.
A machine can generate answers at a scale we have never seen. It is very good at efficiency. It is very good at sameness.
What it cannot do is wonder.
It cannot replace curiosity. It cannot replace judgment. It cannot replace conviction. It cannot replace the humility to sit with a difficult question longer than is comfortable.
The more intelligence becomes abundant, the more identity matters.
The brands that remain rare will not be the ones with the most technology. They will be the ones that know who they are.
The same is true for people.
A few days later, I watched Estee at her recital.
No nerves. She walked onto the stage confident and happy to be there.
She may never need calculus. She may never need the five-paragraph essay structure I learned at U Chicago and still use today. AI may handle much of that.
But she will need confidence. She will need judgment. She will need curiosity. She will need the courage to think for herself.
Those are things no technology can provide.
Maybe staying rare, whether as a brand or as a person, is not about resisting change.
Maybe it is about knowing yourself well enough that change does not erase what makes you distinctive.
And perhaps that is the greatest foundation we can give our children.