I’m currently engaged in a lesson with my four-year-old that every parent reader has taught their own kids—how to cross the street safely. We’ve practiced together under the safety of hands held: look left, look right, look left again. He’s pretty much got it down, but he still occasionally makes mistakes. So I’m letting him make them while keeping close watch within grabbing distance to prevent him from marching out into traffic.

I feel like this comparatively easy experience is emblematic of the parenting struggle that persists through the teen years. He’s not ready to do this by himself. To send him out there on his own would be negligent. But at some point, he’ll simply have to learn to do this without me holding his hand (that’s why you never see seventh graders crossing the street connected to a parent). And the critical step towards getting there is to let him make mistakes, but without abandoning my watch until he’s learned the skill. The mistakes are part of the learning. And I have to let him make them.

This short video featuring Challenge Success’s Madeline Levine reminds parents of this lesson. If we’re constantly stepping in and handling challenges for our kids, they won’t learn how to handle challenges that inevitably arrive without us close by. She relates the story of a freshman on the Stanford campus who can’t remember where her first class is and decides to solve that problem by calling her mother. That’s not a joke—this kind of thing happens all the time these days, even with the most accomplished kids on the most selective colleges’ campuses.

There’s no playbook telling parents exactly when to step in or step out. But when in doubt, give them some guidance and let them try. If the cost of failure is minimal, let them fail. If not, stay literally or figurately close by, ready to step in, but only if absolutely necessary.

It’s our job to keep them safe, but also to help them develop into capable young adults. And they’ll be more prepared for any obstacle when instead of relying on our hands, they rely on that challenge’s version of left, right, left again.