“You are the coolest dad ever…”

Those were the words of my son, wide-eyed and baffled as he watched me ollie his new skateboard. An ollie is a simple trick I used to do as a kid, stomping the tail of your board on the ground with one foot and popping it into the air while you ride it. Jumping on his new Santa Cruz, it came back to me in an instant, like riding a… skateboard. In that moment, I was fourteen again.

This skateboard is really sanity on four wheels as far as he’s concerned. Theatre is canceled for the summer, and although he gets to hang out with friends from time to time, COVID-19 has flipped his life upside-down. This skateboard might save summer for him, just like it saved my summers in the early nineties.

Yesterday, as we were standing in the driveway, this insightful 14-year-old shared five things he’s learned since he started riding – reminders we can all use…

  1. You have to be willing to take risks and try new things. Risk is an essential part of life, whether it’s stepping onto an unstable skateboard, starting a new career, or telling someone you love them for the first time. In those moments where our outcomes are unknown, we’re required to become vulnerable and exposed. Every new thing we try comes with some of that, but we need to remember that risk is our launchpad – we don’t experience the wins if we don’t put something on the line first.
  2. You can’t give up if you fail on the first try, or the twenty-third for that matter. You never land a new trick on your first try or the second. You have to expect failure in the beginning, and over time you’ll get closer and closer to nailing whatever trick you’re trying. The key is not to give up – to commit and go all-in.
  3. When you fall, get back up. Not if, but when. If you’ve embraced failure as part of the process, then falling is an equal part. So, with that in mind, every time you fall, you have to get back up. Failure, falling, and getting back up are all intimately tied together – getting back up is the most important piece of that puzzle.
  4. You can be afraid, but you can’t let the fear own you. This is another “not if, but when” concept. You will eventually be afraid. Whenever we take risks and face the possibility of failure or getting hurt, fear creeps in. The reality is, we can’t ever stop fear from showing up, but we get to choose how much power we give it. Will it stop us, or will we be brave in the face of our fear and keep moving? 
  5. Protect your head. This one goes way beyond just wearing a helmet. Mindset is everything as you’re trying new things, getting back up from your falls, and facing your fears. If your head’s not in the right place, then quitting and giving up will quickly become realities when you fall, fail, and encounter adversity. 

These lessons seem especially fitting right now. Next year will be my son’s first year in high school. He ended middle school virtually, and there were no tours of the new high school, which makes the transition a little awkward and scary – which he is mature enough to admit openly. Frankly, none of us know what the coming year will even look like. The things he’s learning on that skateboard, though, are teaching him to be resilient, daring, and tenacious.

This skateboard will come with some scrapes, probably a little blood, and that’s just fine. My new board is on its way, and soon we’ll be skating together. The old man has a few more tricks to teach yet…

The Takeaway

What’s your skateboard? What’s that thing that will help you rekindle your fire and stretch you past your comfort zone? And when you try it, how will you embrace the challenge of trying something new, falling or failing, and getting back up?

Let’s make this the summer where we stretch ourselves beyond our limits and do something uncomfortably awesome.

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