We were somewhere between a dusty diner’s parking lot and an old ghost town when I started passing my bright list of ideas around the backseat. “Everyone choose something you want to do! Our first act of kindness is coming up!” I gleefully said.
My family of five was on what we affectionately refer to as a “Kindness Quest.” It was our second such trip and my minivan made our mission loudly obvious. #KindnessQuest and slogans like “Kindness is Cool!” were scrawled across the windows with paint pens. Our rainbow mascot was perched in the front seat. The kids were now passing around a flamingo notepad and writing out what we called “encouragements.” We would leave notes with encouraging words such as, “Never forget how awesome you are!” or “In case no one told you recently, you’re important!” on a few cars and public boards while we explored.
We were on a mission — and we’ve been on several since then.
Road trips with kids can be hard
I’d always loved road trips, but it wasn’t until a cross-country move that I realized how much I enjoyed unhurriedly exploring the United States with my kids.
But, as anyone who has been trapped with children in a moving vehicle for an extended period of time knows — it’s hard work. I often switched into survival mode as we traveled, keeping them happy with snacks and movies. But even then, I felt frustrated. Something was missing. Our road trips needed something to bring us together.
I yearned for something more for us
There’s a familiar tension many families feel: How do we raise children of compassion? How do we lead kids to care? I knew I wanted to model something different for our family with presence, intentionality, and social awareness at the core.
What would it look like to take those values on the road? My sister-like housemate joined my brainstorming and the “Kindness Quest” was born. Answering these questions became our roadmap as we took to the road.
We started big
The first summer, we went all out — driving from Mexico to Vancouver and back. We tie-dyed shirts. We packed a large box full of supplies, like candy and markers, to help us practice kindness along the way. And we started the trip by knighting the kids with foam swords and encouraging them live out missions of compassion.
But doing acts of kindness on the road was more challenging than I expected. Sometimes it took extra perseverance that could led to time away from what we wanted to be doing. Some of our handmade PB&Js and balloons with messages of encouragement scrawled across them were rejected by our chosen recipients. My kids had meltdowns. Sometimes we got upset with each other and had to learn how to forgive.
Despite some setbacks, the quest bonded us through laughter, wonder, and a boatload of joyful memories. Through these acts of kindness — whether passing out donuts or asking a stranger for advice in exchange for a flower — my kids grew in both confidence and resilience.
We’ve also learned to question our motives along the way. Are we being ethical? Are we virtue-signaling? These quests have sparked real discussions about how to come alongside people in need, rather than assuming we know what’s best.
Our mission has evolved, but our goals remain the same
Over the past seven years, our expectations for the quests have shifted. The kids have grown, a baby was added to the mix, and some health issues have complicated things. But this tradition has shaped my family. Ultimately, we’ve all learned to notice and love people better.
When I think back to one of our early travel days, I remember noticing something on our own windshield when we returned to the car one afternoon. It was a napkin, transformed into a note of encouragement for us. It told us to keep the kindness going. And this summer we’re trying again.
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