A few winters ago, I dropped my five-year-old daughter off for her first day of ski school. She was the youngest in the group, struggling even on the bunny slope. By lunchtime, her instructor warned me that she might not be ready, and I had a knot in my stomach.
I skied by the group to casually see how it was going. She spotted me immediately and lifted her goggles; I could see her eyes welling up.
We got home and my daughter burst into tears. I took a breath. I was about to tell her she could try again next year. She beat me to it.
Through tears, with complete conviction, she said, "I'm going to go back there, and at the end of the season, I'm going to win the trophy." I asked what trophy, and she didn't know. It was an aspiration that made the challenge seem real.
Her instructor had said she might not be ready. But I had to let her try.
Ten weeks later, she had put in the work and won the trophy.
What my daughter did wasn't about a trophy. It was about setting a goal. She was also learning that the most powerful goals aren't finish lines; they're starting points. She had to imagine it was possible, learn how to do something hard, and stay with it. That's how confidence gets built.
Play is where children first practice these skills. Through sports, games, and imaginative play, they cultivate creative thinking. They also cultivate problem-solving, empathy, perseverance, and collaboration — qualities that are indispensable for success in adulthood.
My daughter has that trophy photo. She looks, understandably, like she owns the mountain.
But what she really came away with that season was something harder to capture in a photograph: the experience of setting an aspiration, struggling through uncertainty, and discovering she could handle more than she thought. The trophy was simply the marker.
When the goalposts keep moving and certainty is increasingly rare, the people who thrive rarely have all the answers upfront. They are willing to dream and try, to adapt and then dream again.
Those are not skills most people first learn at work. They often begin much earlier through play. The best leaders I know never stop playing.