Let's Say Yes!

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, diligent S-turns and I made it down in one piece. Better than in one piece—I was proud of myself for trying something new.

Later that afternoon, when Leopold and I were reunited back at the lodge, he asked if we could go in the outdoor hot tub. Mind you, it was a 20-degree day, and the only thing I hate more than being cold is being cold and wet! When I started to demur, Leopold invoked our pact.

Yes, it was cold, and yes, I was wet. But it was also invigorating to feel the cold air on my skin, and the warm water of the hot tub felt that much ­better once we got in. Getting out was a different story, but the experience was a delight as Leopold and I braved it together.

The author and and the family on their trip 

We had so much fun saying yes to everything that Leopold and I decided we should get the rest of the family—his dad and sister—on board during our spring break trip to St. Augustine, Florida. We collectively said yes to a moonlit ghost tour of the city’s allegedly haunted sites, including a century-old jail and gallows. While others in the group got claustrophobic and left the creepy jail cell during the telling of ghost stories, Leopold and I stayed until the bitter end.

On that same trip, Leopold tried his first spicy tuna roll, and his sister, Nola, sampled blackened grouper. I went in the freezing ocean because Nola asked me to. I not only survived, I enjoyed it, as we had the whole ocean to ourselves.

On our summer adventures, we continued the tradition of saying yes. For me, this meant going down a scary 90-degree waterslide at a water park. Again, the only reason I did it was because my daughter asked me to. You know what? It was pretty fun, though next time I would plug my nose. Leopold braved the ropes course and made it all the way up to the top.

When we went to Yellowstone for our big family vacation, saying yes led us to take a 25-km bike ride in Jackson Hole, go line-dancing at a country-­western bar and ride horseback through a national forest. On the last night of our trip, at the rodeo in Cody, Wyoming, neither my son nor my daughter hesitated when all the kids in attendance were invited on to the field to take part in the traditional calf chase. Though neither came back with the prized bandanna, they were both laughing, sweaty and excited. I know it’s an experience they’ll never forget.

While visiting Yellowstone, the author and her family said yes to trekking through the Shoshone National Forest on horseback

And therein lies the beauty of saying yes on vacation: It pushes you to bust out of your comfort zone. Though it’s not always possible to say yes to everything back home, where work, school and other obligations can get in the way, we’re trying to say it more. Cultivating a sense of adventure helps us live life to the fullest—even if you sometimes wind up cold and wet.