Learning to Fall: What Skateboarding in My 40s is Teaching Me (and My Kids) About Failure
I started skateboarding recently. In my 40s. I mean, I fooled around with a board in my teens and twenties, in someone’s cul-de-sac or cruising up and down the Mission Beach boardwalk. There were also the skateboard-keg shuttles in college (but that doesn’t really count).
I am clumsy by nature. My children are not. They are also not afraid to fall, much more agile, and more daring than I’ve ever (EVER!) been.
I love a park for about an hour. I can read, catch up on a few emails, play a little. And then I’m over it. If I can work or have a good book, I can stay a lot longer. But, we had started spending hours at skateparks. I was getting bored.
After about two months of this, I thought, well, maybe I’ll learn to skate. My husband is out there too, and I didn’t want to be another girl sitting on the sidelines watching. But, truly, did I want to be a middle aged woman falling off the ramp? I didn’t know, but I thought I’d see.
Almost everyone one I spoke to about this had a similar reaction. Maybe it’s exactly what you are thinking too — “You’re going to break your hip.” Seriously. About six people said this. “Are you sure….?” came from my more tactful friends. My 12-year-old, almost pro skater said, “Ooh! Aunt Jess! I can’t wait to see this!” and then giggled and told his cousin.
I wasn’t really sure if I was going to, but then we were at the used sporting good store, looking for baseball gear, and there she was … my new board. Sunset on the deck, trucks, wheels, and all of it already put together, and cheap! (Thanks Mike!)
The First Fall
Inching around the skatepark the first time, I fell almost immediately. Not a graceful fall either – full-on splits that made me question choices I’ve made in life. My kids watched, wide-eyed, maybe a little scared, waiting for my reaction.
They ran to me to make sure I was ok, definitely a little worried.
I laughed (after checking that everything was still intact).
Something shifted. They realized how bad I was at this. After seeing their dad do things they can’t even dream of, what is their mom doing? I mean, seriously, what was I doing? But they also realized, I didn’t care that I am bad at this and all this terribleness could be pretty funny.
My son, who had been struggling with perfectionism in school, looked confused. “You’re not mad?” he asked.
“Why would I be mad?” I replied, dusting off my hands. “I’ve literally never done this before. Of course I’m going to fall.”
Being Terrible Together
Within a few minutes, I had realized something: my kids rarely see me be bad at things. Not just bad, but comically, embarrassingly, falling-on-my-butt bad.
They see me cook dinner with confidence, work with competence, drive a car like I was born knowing how.
All the things I’ve had decades to master (this might be too strong a word — I am not sure if I’ve “mastered” dinner, but it gets done) look like they come easily to me – because they do now, after years of practice.
But my kids? They’re beginners at almost everything. Every day asks them to try something new, to stumble through, to feel that uncomfortable stretch of incompetence.
Skateboarding is for an opportunity to watch me literally fall, get up, try again – and usually with a smile.
What I Didn’t Expect
I didn’t expect to love it. But there’s something freeing about doing something purely for the joy of learning. I’m not going to be competing in the X Games (unless they create a new category for middle-aged beginner women). I’m just trying to stay on the board, get down the ramp, and stay out of everyone’s way, all without embarrassing (or seriously hurting myself).
I didn’t expect it to change my relationship with my kids. But it has. They are my cheerleaders. “You know you’re getting better when you fall,” my little one assures me after I hit the concrete pretty hard. The big one offers what he considers high praise: “You’re pretty good for a middle-aged lady.” (Thanks, Bud.)
I certainly didn’t expect it to become a metaphor for so much of what I believe about parenting and life. But here we are.
The Permission to Begin
“Was it embarrassing when everyone saw you fall?” my son, the perfectionist, asked after a particularly public stumble.
It was. But what he doesn’t know is that it’s embarrassing just being out there, being a middle-aged, beginner mom, fearful of even the tiniest ramps.
“A little,” I admitted. “But I’d rather be out here with you guys, having fun, and trying something new than worry about embarrassment.”
I could see him processing this, tucking it away for later (or at least I hope). Permission to begin. Permission to be bad at something new. Permission to fall, laugh, and try again.
The Upside-Down Reality of Being the Beginner
As parents, we’re almost always in the position of being “better” at things than our kids. I hadn’t fully appreciated this until I was the one admiring their skills and getting tips from them (my five-year-olds are usually somewhat questionable, but sweet).
My little one is in absolute awe of how well I can draw a heart (I’ve been drawing hearts for 40+ years, so I should hope I’ve mastered it by now.), meanwhile looking at his own with despair. They are constantly amazed at how fast I can write a to-do list.
Even in sports where I’m objectively terrible, in those early years, they think we’re practically pros. Yes, I can hit a baseball with a bat if I throw it up myself, but I’m last in the batting order when we have our annual adults against kids softball game.
There are very few activities where our children get to be better than us, especially when they’re young. Which makes skateboarding uniquely valuable for us.
The Unexpected Benefits
Beyond the philosophical benefits, there have been some unexpected practical ones:
- I’m no longer bored at the skatepark. I’m too busy catching my breath and trying not to break my wrist.
- I’m connecting with my kids in a new way. They’re teaching me, encouraging me, cheering for my smallest victories. The role reversal is beautiful to witness and unbelievably fun.
- I’m getting exercise without it feeling like exercise. My body, firmly in its 40s, appreciates this sneaky approach to movement. I can see a difference in my abs without a single plank.
- I’m remembering what it feels like to be a beginner. This makes me a more patient parent when my kids are struggling with new skills.
- I’m showing them what it looks like to be terrible at something and keep going. This might be the most important benefit of all.
The Most Important Lesson
My kids are both fairly coordinated and somewhat natural athletes (they definitely did not get that from me). And while it’s still very early school hasn’t been too challenging. So when they encounter something difficult, they tend to struggle emotionally and want to give up. And the self-talk is just heartbreaking.
Skateboarding has given me the opportunity to show them, “Hey, look at me—I am really bad at this. After months, it’s clear I will never be good, while you two are already amazing. But I just have to keep trying, falling, feeling a little embarrassed, getting a little better each time, having fun, and not giving up.”
This is a fundamentally different message than when I remind them that with time and practice they’ll get better, while demonstrating a skill I’ve had decades to master. They can’t relate. But watching me struggle? That they understand.
It’s also about showing my children how important it is to be a lifelong learner. That there isn’t an arbitrary age when you’re “too old” to try new things or look silly or fall down in public.
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We’re all beginners at something (motherhood?). We all fall (again, motherhood?). I’m hoping by failing miserably and literally falling on my a**, I’m modeling resilience, the ability to fail, and the joy of trying new things as well as an “I don’t care how I look, I’m having fun” attitude.
Because I can talk all day about perseverance and getting back up and the learning curve and blah blah blah, but actually showing them what it looks like to try something new and do it badly is ok. And we all have to start somewhere.
Teenager Jess would be so proud…
