Why I Skateboard at 50

Scott Connelly
6 min readJul 1, 2021

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Family skate session at Switch & Signal Skatepark

Although I skated in high school and even had a skate-messenger job in college I haven’t skated in over 25 years. In the fall of 2019, I took the kids to an intro to skating session and they had a blast. That planted a seed, just hearing boards rolling and the tell-tale sound of decks snapping against pavement made me want to skate again. At the time I brushed that feeling aside and figured I was too old, but slowly started watching skate videos now and then. A few months later I caught X Games 10 Years of Real Street and Mike Vallely talked about what it was like being a skater at age 44 (back in 2015) and what it meant to be voted fan favorite that year. It struck a chord with me and that seed started to grow.

Mike Vallely taking about being an older skater (2 min starting at 31:10)

The skate scene that I remember from my teen years was very competitive and lessons didn’t exist, other than watch and try to figure it out. I came from a background where maybe your friends would show you a few things and you would push each other, but learning was hard. The only videos were professional skaters demonstrating tricks well above my skill level. While I could appreciate the skill involved, trying to replicate was difficult at best. The last time I skated back in college I was trying to teach myself how to drop in on a half-pipe. It ended with me destroying my ACL and effectively ending my early days of skating. Last October I decided to take an adult beginner skateboarding class at Switch & Signal Skatepark. The environment at Switch & Signal is very welcoming. I was nervous going into my first lesson, it was adults, but predominantly twenty-somethings or early thirties at the most. I thought maybe I was in over my head, but everyone was incredibly nice and very supportive. Kerry and Neil are patient instructors that create a great environment to learn. They know how to break things down while keeping things comfortable, but also present challenges when the time is right. I forgot how much I missed skating and have regularly been to weekly lessons and open skate sessions since.

After a month or so, my daughter joined me for an open session and we had a blast. We both accomplished skills that we hadn’t done before. It was a good lesson for her and a good reminder for me. One of the things I love about skating is the feeling of accomplishment, of putting in the work and achieving something new. That we could both experience it at the same session was even better. It made me remember being her age and recall the difficult times and anxiety of being a teenager. For me, skateboarding was a valuable outlet. All the practice and attempts would help me clear my head, burn off excess energy, and refocus on what was important. That feeling of finally breaking through and landing a trick is an invigorating and uplifting moment. She caught a sense of that feeling and has been to almost every lesson and session with me since. My twin boys joined us shortly afterward for sessions and a few kids’ lessons. While one of them is still deciding if skateboarding is for him, the other has accelerated at a pace that is amazing to watch. He is constantly asking me, “Dad, when can we go skate?”

To the outside observer, skateboarding appears as a sport wrapped up in a rebellious subculture. While that is true, it is so much more. What many people don’t see are the hours, days, weeks, months, and years spent learning some of the skills. There is a great deal of effort and perseverance required when trying to do anything on a skateboard, from day one just rolling around to doing tricks on curbs, ramps, rails, and everything in-between. I can not say how many times I have seen some accomplished skaters come in for a two-and-half-hour session and work on one trick, trying over and over, making adjustments, falling, and failing a lot. What separates skateboarding from other endeavors is that when attempting certain tricks, even if you have done them many times, you have to push through fear. Fear of falling, fear of pain, fear of failure, and give it one more try. You force yourself to fight through those fears, commit, go all-in, and take a leap of faith. Skateboarding is also an art. No two skaters will perform a trick exactly the same way. There is an abundance of style, creativity, and nuance involved. When everything comes together in a run or even a single trick, something beautiful happens. It is a heightened awareness, a connectedness with the board and the surrounding environment. Every skater has felt this at one time or another. This is at the heart of skateboarding.

My son dropping in on his own
Dropping In

Flashback to 1991 and the incident that ended my early skate “career”. I was learning to drop in and it ended poorly. Fast forward to a few months ago, and my now 12-year-old son gave it a go a few times. He worked on it in lessons with instructor support and started to get the hang of it. After a few more sessions, he decided to give it a go on his own. He slammed hard on his first three solo tries and then bagged it for a few sessions. What I loved was that everyone in the park stopped to support him and cheer him on for every try. Even though he fell, he got back up and tried again and made a bit of progress with each try. To watch him now you would think he’s been dropping in since birth. But several subsequent sessions started with, “Hey Dad, can you stand near me…” and I did, and it’s all ghost hands because he doesn’t need me, he just needs to remember his confidence and he has not fallen, not once, since those first three attempts on his own. Recently, I noticed his back foot was shaking a little before he dropped in for what was likely at least the hundredth time. I asked him if he was nervous or scared and he said, “Dad, I’m scared every time I drop in.” To say I was proud was an understatement, to say I learned something about both of us is an understatement. As a parent you know that there are some things that you simply can’t tell your children, experience is the only teacher that will allow that lesson to sink in. He commits to doing something that scares him and pushes through that fear. That is an incredibly valuable life lesson that extends well beyond skateboarding. My children inspire me so much. We skate together as often as we can and to watch my daughter learn new tricks and see my son pass me by is beyond stoke. It is EVERYTHING. It is why I skate, it is why I breathe. It is passing on something I hold dear to my children and watching them embrace this art-sport-lifestyle and make it their own.

I turn 50 in today, and, yes, I still fall sometimes, but I’m getting better at it, at least the falling, if not the skateboarding. I am still trying to conquer 25-year-old demons, pushing myself to drop in. I’ve slammed a few times and it sucks, pads and all. Don’t get me wrong those slams hurt… a lot… but in the midst of that pain, something else arises. I am still alive! I am present in that moment, amazed that I can stand up, and then the adrenaline kicks in and I am ready to give it one more try. Sometimes a good jolt is needed, a smack in the face helps me remember how resilient I am, how durable my often achy body truly is, and to know that a fall won’t kill me. Yes, I may have some aches, pains, and annoyances the next day, but the feeling of not trying, not pushing through is exponentially worse. The sheer joy of trying a new trick, let alone landing it, is a feeling that is hard to describe if you haven’t been there, but so worth it.

I am a 50-year-old skateboarder. I hope I can keep skating as long as I am alive… just like this 80-year-old shredder…

Mr. Kinoshita shredding at 80 years young

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