Teaching My Daughter to Hitchhike (Sort Of)

It wasn’t exactly part of the parenting plan.

But we also did not know we would have to figure out what to do if Uber cancels in remote area.

We were outside Flagstaff, Arizona for a ski day at Snowbowl—one of those crisp, bluebird mornings where everything feels easy. Getting up the mountain, however, was anything but.

Despite weather warnings and 4WD requirements, our Uber driver agreed to take us. He spent the entire climb up the rutted, icy road reminding us just how questionable that decision was. But we made it.

And the day? Perfect. Great snow, sunshine, and the kind of memories you hope stick.

Then came the trip down.

We opened Uber. Tried once. Nothing. Twice. Nothing. A third time…finally, a driver accepted. We watched the little car icon make its way toward us—hope restored—until it reached the base of the mountain…and cancelled.

Just like that, we were stuck. The resort was closing. The parking lot was thinning out. No ride. No backup plan.

So I told Rachel to wait near the ski rental area, somewhere visible and safe. Then I headed into the parking lot and started asking strangers a simple question: “Any chance you’ve got a couple extra seats heading down?”

Seven or eight polite “no’s” later, I heard a voice behind me—young, matter-of-fact:

“Dad, I think those people need a ride.”

The dad walked over, I explained our situation, and without much hesitation, he said yes. We squeezed in with him and his two sons and started the descent.

What started as a logistical problem turned into one of the best parts of the day. We talked about their boys—college plans, career ideas, what’s next in life. Easy conversation. Good people.

Then we realized something unexpected: their route home took them right past our hotel.

Door-to-door service.

As we pulled up, I offered the dad $50 as a thank you. He smiled, pointed to his son, and said, “He needs the college money.” The kid accepted it with a grin that said it all.

The Lesson

I joked with Rachel that I was teaching her how to hitchhike—but really, it was something else.

It was about staying calm when plans fall apart. About being willing to ask for help. About thinking a little differently when the obvious solution isn’t working.

Most people won’t say yes. That’s fine. You only need one.

And sometimes, the solution isn’t in your phone—it’s in the people around you.