“Do you think you could walk ten miles?”

That was the question that I asked as he was about to graduate from high school and begin college.

Over the years I’ve witnessed countless milestone moments in his life. I remember him taking his first steps. His first lost tooth. First communion. Learning to ride a bike. Confirmation. Getting his driver’s license.

For some reason, graduation triggered more emotion for me. Perhaps it was because it was the last big milestone that he would experience while living under my roof.

I wanted to commemorate this milestone with something more special. So I asked him if he could walk ten miles.

With great confidence he assured me that he could walk that far. He wanted to know why I’d asked such a strange question. Then I told him that I wanted to send him on a hike. A ten-mile hike.

For the past eighteen years, he has walked a lot of miles, but never alone. Whether he was aware of it or not, my son had been “surrounded by a cloud of witnesses.” He’d been influenced, cared for, prayed for, encouraged, and taught by adult relatives and friends who truly loved him.

My wife and I contacted ten people who have had a significant impact on our son’s life. We thanked them for all that they had done for our son the past 18 years and then we asked if they would walk one more mile with him before he set off to college.

We asked each person to be at a specific place and time along a route that we had planned out for his walk. Ten people spread out one mile apart for ten miles. Each of them would walk side-by-side with our son for one mile – talking about whatever they wanted to talk about.

These ten exceptional people included grandparents, aunts, uncles, godparents, and special adult friends. The group included our son’s daycare provider and his first camp counselor who actually flew in from Chicago for a twenty-minute walk!

What each person chose to share along the route was up to them. Grandpa brought along a boom box and played some silly songs that used to make them laugh. Grandma brought along some of his favorite bars to eat along the way.

Some talked about the past. Some talked about the future. They shared favorite memories. They asked questions. They talked about faith. Since the route looped through the neighborhood where I grew up, we strategically place his aunt and uncle through that part so they could share some family stories that he had never heard.

When the walk was over, we all gathered for a celebration picnic. It was a milestone day that my son will never forget. He still has a framed collage with the map of the route alone with photos of each walker.

 “Therefore, since we are surrounded by such a great cloud of witnesses, let us throw off everything that hinders and the sin that so easily entangles. And let us run with perseverance the race marked out for us, fixing our eyes on Jesus…”  Hebrews 12:1-3.

Our lives are not solo expeditions. We need to surround ourselves and our kids with people who will encourage, influence, teach, pray, and care for us along the journey.

Milestone markers are important ways for us to remember where we have been, where we are going, and knowing that we are travelling the right route.