Where the Sidewalk Ends

When my children grew past nursery rhymes and fairy tales, we found ourselves on a new shelf: poetry. That’s when Shel Silverstein’s Where the Sidewalk Ends entered our lives.

I can still picture it — the way their eyes lit up as his crooked lines broke apart the neat rhythms they were used to. The words tumbled into absurdity, wonder, and questions that clung long after the book was closed. What began as bedtime reading became something more: proof that imagination doesn’t need permission, only a spark.

For me, it was also a quiet confirmation of something I had long believed but hadn’t named: that the stories we carry really do shape the lives we live — not only our own, but the ones we share them with.

Sidewalks, after all, are supposed to be safe. Straight. Predictable. The poured paths someone else laid down for us. They don’t ask questions. They don’t leave room for wandering. They give the illusion that everything important can be neatly contained between the curb and the fence line.

But Silverstein pointed toward the edge. And the edge is where things get interesting.

When the sidewalk ends, the script falters. There’s no map, no curb to guide your steps, no certainty that the ground ahead is level. It’s unsettling. And yet — it’s also the only place you discover what imagination is really for.

That book was supposed to entertain my kids. Instead, it reframed something for me: sidewalks are the life we inherit. The space beyond them is the life we choose.

And that, I think, is where so many of us get stuck. We confuse safety with meaning. We tell ourselves that staying between the lines is the point. But the stories that linger — the ones that take root in our children, our friends, our own late-night reflections — are almost always born at the edge, where something ended and we had to improvise the next step.

The older I get, the more I’ve come to believe that this is what art is really for. Not to pave over life with something smoother. Not to offer escape routes that keep us comfortable. But to hand us back to ourselves when the sidewalk runs out. To remind us that endings are beginnings in disguise, and that the world asks less for compliance than for curiosity.

My kids don’t remember every story we read together, but I can still hear the way they laughed at Silverstein’s bent humor, how they repeated certain phrases as if they were spells. That’s what echoes do: they don’t vanish when the page closes. They travel forward, reshaping how we notice the world, how we make sense of its dissonance and delight.

And maybe that’s the point of carrying stories at all: to name what can’t be contained in sidewalks. To give voice to what doesn’t fit neatly between painted lines. To leave behind a signal that others can follow when their own path falls apart.

Because the sidewalk doesn’t end when the builders ran out of cement. It ends because imagination begins where certainty stops.

That lesson — learned on a bedroom floor with my kids years ago — still echoes. It’s why I write, and it’s why I believe stories matter.

If this resonates, you might enjoy The Signal — my letter where I share small echoes and questions like this, meant to be carried into your own days.