Yesterday we went for a family hike at Mission Trails, choosing a trail we had never explored before.

Standing in one particular rocky section of the trail, I suddenly wasn’t a forty-one-year-old dad anymore.

I was a little kid again.

I was back at Lake Jennings and Lake Cuyamaca, camping with my dad and grandpa. My sister and I would wander along the shoreline, climb over giant rocks, cut through the brush, and explore whatever happened to be around the next bend. We rarely knew exactly where we were going, and that was part of the adventure.

Yesterday, hiking with Brooks and Joseph, I had that feeling again.

We had planned to hike the Grasslands Trail. Starting from the dam, we were supposed to climb the stairs, complete the one-mile loop, and head back.

Instead…

We missed the turn.

Or maybe we ignored it.

Either way, we just kept walking.

The trail led us across wooden bridges, through clusters of trees, and eventually to a section where the path disappeared beneath the rocks. Brooks hopped from rock to rock while Joseph tackled them as if each one were Mount Everest. Before long we found ourselves looking down at the dam from the Grasslands Trail before making our way back toward the main path and eventually to the car.

It wasn’t the hike we planned.

It was better.

What struck me most wasn’t the scenery.

It was the difference between how the boys approached the trail and how Jillian and I did.

Brooks and Joseph were perfectly content to keep walking.

Sometimes they ran ahead.

Sometimes they stopped to examine a stick, a rock, or a patch of dirt.

Sometimes they wandered off the trail because something looked interesting.

Not once did they ask where we were going.

Meanwhile, Jillian and I had our phones out studying the trail map, trying to figure out where the path led. We even stopped to ask other hikers if they knew what was ahead.

Somewhere along the way, adults become uncomfortable with not knowing.

Maybe that’s just my anxiety talking.

Or maybe it’s something many of us slowly learn.

Before trying a new restaurant, we read reviews.

Before leaving the house, we check the weather.

Before taking a road trip, we map out gas stations and rest stops.

Before buying something, we compare prices.

We spend so much time trying to eliminate uncertainty that we sometimes remove the mystery from the experience itself.

Children don’t do that.

They see a trail.

And they start walking.

While writing this article, I came across an essay by Tim Mathis titled “Why Do People Go on Adventures? It’s So Simple That Even a Child Could Understand.” One idea especially resonated with me: children don’t need elaborate reasons to explore—they’re naturally curious. Somewhere along the way many of us trade that curiosity for certainty. Yesterday reminded me that maybe we’ve got it backwards.

That unfamiliar trail gave us something no map ever could.

Wonder.

Every turn raised another question.

Would there be another bridge?

Another climb?

Another overlook?

Where does this trail actually go?

The adventure wasn’t waiting at the destination.

It was living in the unanswered questions.

While thinking about that, I also came across a wonderful article from Local Passport Family about raising curious and creative kids. One of their ideas was that curiosity grows when children are given opportunities to explore, imagine, and discover things for themselves. Watching Brooks and Joseph yesterday reminded me that they weren’t looking for the destination—they were completely captivated by the journey.

As I thought about it later that evening, I realized I approach much more than hiking this way.

I want to know how the book ends before I write the first chapter.

I want to know exactly how much weight I’m going to lose before I commit to healthier habits.

I want to know whether an idea will succeed before I invest my time in it.

I want certainty before I begin.

But life rarely works that way.

A few days ago I wrote The Belt Isn’t Earned on Test Day, about trusting the process instead of focusing only on the outcome. Yesterday I wrote Adventure Is Closer Than You Think, reminding myself that meaningful adventures don’t require traveling across the country. This hike added another lesson to that list.

Sometimes you have to start walking before you can see where the trail leads.

That’s how writing works.

That’s how marriage works.

That’s how raising children works.

That’s how building a healthier life works.

That’s how building a better life works.

You don’t get the whole map.

You get the next step.

Yesterday I was hiking with my boys.

Thirty years ago I was hiking on camping trips with my Dad.

Maybe thirty years from now Brooks and Joseph will be out on a trail with children of their own.

I hope they leave room for a little uncertainty.

I hope they don’t always feel the need to know what’s around the next bend.

Because sometimes the best memories begin with a simple decision to keep walking.

And sometimes…

The best trails are the ones you never planned to take.

Continue the Journey

If today’s story resonated with you, you might also enjoy:

Adventure Is Closer Than You Think — Why meaningful adventures don’t require a plane ticket.
The Belt Isn’t Earned on Test Day — Why progress comes from trusting the process instead of chasing the outcome.