We Tried Saying Yes to Everything on Vacation—Here’s How It Pushed Us Out of Our Comfort Zone
Updated: Nov. 17, 2023
What started out as a way to get my son to try new foods opened up a world of adventure for my family
Last winter, 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 as much as feasibly possible while on vacation. You see, Leopold is a picky eater—he subsists only on chicken nuggets and yogurt—and can be hesitant to try new things. According to him, it’s because he has numerous phobias, including heights, spiders and the dark. Though in actuality, I suspect he just has normal kid-sized jitters.
My original goal was simple. 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 successfully a handful of times since watching the movie of the same name a few years back. A yes day gives kids the power and responsibility to make decisions, while as a parent, I enjoy that it takes that same pressure off. Before the trip, Leopold and I agreed we would say yes to everything—including food and experiences, especially new ones.
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The yes experiment begins
We started saying yes to new things before we even boarded our flight to Denver 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 in Keystone, 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 on actual fresh, deep powder snow. My hope was that Leopold would say “yes!” and make the most of this opportunity.
While Leopold was in snowboarding school, I skied by myself. On the first day, I played it safe and stuck to the same long and winding easy green run that I was comfortable with. 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 chair lift. In the spirit of camaraderie, I challenged myself to ski an intermediate blue run. There was a part of the run that was a little 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 Keystone Lodge & Spa, he asked me to 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 pack and I acquiesced. Yes, it was cold, and yes, I was wet. But it was also invigorating to feel the cold air on my bare 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 entire experience was a delight as Leopold and I braved it together.
Making it a tradition
We had so much fun saying yes to everything that Leopold and I decided we should get the rest of the family, including my husband and younger daughter, on board during our family 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 on the tour got claustrophobic and left the creepy jail cell during the telling of ghost stories, Leopold and I stayed until the bitter end and didn’t even scream when one of the actors attempted to frighten us with a jump scare.
On that same trip, Leopold tried his first spicy tuna roll, and my daughter experimented with blackened grouper. I went in the freezing April ocean, because my daughter asked me to, once again getting cold and wet. I not only survived it—I also enjoyed being the only other person besides my child foolish enough to venture into the chilly waters, as we had the whole ocean to ourselves.
The yes adventures continue
On our summer vacations, we continued the tradition of saying yes to everything. For me, this meant going down an insanely scary 90-degree waterslide at the new Great Wolf Lodge in Maryland. The only reason I did it was because my daughter asked me to. You know what? It was actually pretty fun, though next time I would plug my nose when I hit the pool at the bottom. On that same trip, Leopold braved the ropes course and even went all the way up to the top.
When we went to Yellowstone for our big family vacation, saying yes led us to take a 15-mile bike ride in Jackson Hole, go line-dancing at a country-Western bar and horseback-ride through a national forest. On the last night of our trip, at the rodeo in Cody, neither my son nor daughter hesitated when all the kids in attendance were invited onto 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.
And therein lies the beauty of saying yes on vacation. It pushes you to be open to new opportunities and bust out of your comfort zone. Though it’s not always possible to say yes to everything back home (work, school and other obligations get in the way), we’ve begun trying to say it more. Cultivating a sense of curiosity and adventure helps all of us live life to the fullest with zero regrets—even if you do sometimes wind up cold and wet.
