Here at UrbanPromise, we have something called Family Week — think of it like a winter spring break, a chance for staff and students to step away from homework, school lunches, friendship drama, and the everyday pressures to reconnect with family and relax.
Family Week can look like many things — maybe a staycation on the couch with the remote in one hand and popcorn in the other — but rarely does it look like a ten-hour bus ride with your teachers.
So when we asked: “Who wants to sign up for a ten-hour trip to New Hampshire with your teachers… and our rules… for five days?”
Nine students said yes.
At first, it felt surprising. Why choose more structure, more rules, and a long bus ride over comfort and familiarity?
Was it the karaoke-filled bus ride? Perhaps.
The night hikes and snow tubing races? Maybe.
The crisp mountain air, breathtaking views, and yes… wet socks? I hope not.
What may initially draw students in could be any of those things. But what keeps them coming back is much simpler.
“The highlight of my day was when we tied all our separate snow tubes together to make one giant twenty-person tube,” shared one student.
“I want to give a shout out to Mehki,” shared another. “I really appreciate him for making me laugh today and showing me how to do something when I didn’t know how.”
Moments like these.
Every story begins with a question — a yes or a no.
A yes opens the door to possibility. To growth. To connection.
A no keeps things safe and familiar.
At UrbanPromise, we don’t demand an immediate yes. We look for the maybe — because maybe is where courage begins. Maybe creates space for students to surprise themselves.
Sometimes the best growth begins with a simple “yes.”
Growth rarely happens in comfort.
It happens when students tie their tubes together instead of riding alone.
When one student teaches another how to ski.
When laughter fills a freezing night hike.
So no, it wasn’t a week spent warm on the couch.
We stepped out into the winter tundra instead.
And somewhere between the bus rides, the karaoke, and the snowy adventures, our students discovered something important: The cold never bothered us anyway.
And that’s good news!
Evan Williams
Expedition Program Director
