It’s happened more times than I can count. We’ll be in a parking lot or crossing the street, and Elliot slips his hand into mine. (Even though he’s 9 now, he still occasionally holds my hand out of habit.) And every time he does it, a small shiver creeps up my spine. For him, this is just what we do when we’re walking through a parking lot or crossing a street, but for me holding his hand has always been a sort of contract between him and me that says I’ll take care of you buddy, no matter what. But I know that handholding is another of the many dad-son things we do that will happen less and less as the years go on.

While holding his hand and guiding him safely across a parking lot is a relatively easy task, helping him find his way in the world gets a little more complicated with each passing year. And yet it’s my most important job.

Today I’m helping him learn to ride his new RipStik, which is a sort of skateboard with a torsion bar in the center and two caster wheels on the bottom. This thing looks like it was invented when skateboarders ran out of new ways to get road rash. For all I know, the RipStik was made on a dare. I’m not sure what possessed us to buy it for him—skateboards are hard enough to ride and they have four wheels and a full deck. But he had his heart set on it, and he’s a tough kid to disappoint.

When we get home, I move the cars out of the driveway while he puts his pads on. He has his mind set on riding the RipStik today. While he made a few tentative attempts over the past week, using borrowed pads and his bicycle helmet, he couldn’t get a feel for it. He ended up frustrated, saying it was impossible to even get up. Elliot is a quick learner and tends to come down a little hard on himself in the face of failure. When he gets knocked down, it takes him a while to get back up. My primary goal as his dad is to always make sure that he does.

As Elliot stands at the top of the driveway with his left foot on the front of the deck, I tell him to take his time. Then I watch as he pushes off and immediately falls down. Over and over, he gets up and falls—he tries again and falls again. I can see the frustration building, so I suggest that he take a break. While he sits and mopes, I patiently explain everything I’ve learned from watching countless RipStik videos on YouTube over the past week. I want to be Yoda, but instead I come off as Ben Stein, repeating the same thing ad nauseam. He’s about to tune me out, so I offer just a few more encouraging words and head to the back yard to mow the lawn. As I leave, he gets up and tries again.

When I taught Elliot to ride his bike, I put too much pressure on him, pushing and prodding until he didn’t want anything to do with his bike, especially after he fell the first time. Having learned my lesson, I don’t push him quite so hard anymore and give him space to figure things out for himself. While this generally works, there are times when one of us ends up crying. This is starting to look like one of those times.

As I finish mowing the lawn and come back around the house, I see Elliot hanging his head. He takes a spill after finally getting up for a few feet. He’s frustrated and on the verge of tears but he’s still outside, which is a good sign. That means he’s not ready to give up. I want him to get back on the RipStik but I don’t him to be miserable about it. So I ask him what he did to finally figure out how to ride it. After he explains, I ask him to show me. He recognizes my tactic, but he gets up anyway. From the top of the driveway, he pushes off on the RipStik and glides 50 feet to the end, with an occasional wobble but otherwise smooth ride. As he steps off he’s beaming, and my heart explodes with pride.

Before I became a dad, I believed that most of us have children out of a vain belief that we saw something of value in ourselves that deserved to live on for another generation, even if it’s something as simple as how best to navigate the world as someone with our particular genetic make up. With almost a decade of fatherhood under my belt, I can see how misguided I was back then. Being a parent is about so much more than traditions and biological imperatives. Sure, there are plenty of things we pass on to our kids, but there are even more that they pass back to us. They change us at a fundamental level, pushing us to be the best version of ourselves possible. We fall together and we learn together. We persevere and we grow.

The day-to-day reality of bringing up my boys involves a lot more improvisation than I ever thought it would. And it’s about striking a balance, walking the line between enlightened mentor and well-intentioned taskmaster—teaching them in a way that’s not too rosy and simplistic, yet also not too overbearing. Sometimes it’s just paying attention long enough to understand your child’s point of view. That’s where Elliot has taught me the most. From the moment he was born, there’s been a version of myself I see in his eyes that I’ve wanted to live up to. A version that does right by him, by showing him that healthy doses of love, humor, and grit will get him just about everything he needs.

That and a hand to hold in a parking lot.

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