Let's Say Yes!

What started out as a way to get my son to try new foods opened up a world of adventure for my family

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What started out as a way to get my son to try new foods opened up a world of adventure for my family

Last year, as my then-9-year-old son, Leopold, and I were prepping for a mom-son ski trip to Keystone, Colorado, I came up with a rule: We would say yes to everything. You see, Leopold is a picky eater—he subsists on chicken nuggets and yoghurt—and can be hesitant to try new things. According to him, it’s because he has phobias, including heights, spiders and the dark, though I suspect he just has normal kid-sized jitters.

I was hoping to find a way to encourage him without resorting to worn-out adages like “If you don’t try it, you’ll never know if you like it.” So I borrowed the idea of a Yes Day, something our family has done a handful of times since watching the movie of the same name. Before the trip, Leopold and I agreed we would say yes to everything, including food and experiences—especially new ones.

We started saying yes before we even boarded our flight, when we stopped at a breakfast buffet at the airport. For me, that meant I sampled a vegan meatball, while Leopold tried a mouse bite of hash browns he said looked “funny.” Neither of us went back for seconds, but we each rated our respective new foods as “not bad.”

The next day, after we got settled at our hotel, I took Leopold to meet his snowboarding instructor. He had taken a few lessons back at home in Connecticut but had never had the opportunity to snowboard on a mountain of this size. My hope was that Leopold would make the most of this opportunity.

While he was in snowboarding school, I skied by myself. On the first day, I played it safe and stuck to the long and winding easy green run. On the second day, I thought of Leopold, who, the day before, had kept to our bargain and faced his fear of heights to learn how to ride a chairlift. In the spirit of camaraderie, I challenged myself to ski an intermediate blue run. There was a part that was steeper than I would have liked, but I did my slow,...

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