5 Lessons of Growth & Failure From Skateboarding

By Alex Harris November 18, 2020

5 Lessons of Growth & Failure From Skateboarding

View podcast on Apple, AnchorSpotifyGoogle or watch on YouTube.

Santa Cruz hand skateboarding logo

Everything I’ve learned about growth and success I’ve learned from skateboarding.

That’s right, skateboarding.


Skate or Die!
That was my motto as a young boy. FYI - Skate or Die was also a skateboarding video game released by Electronic Arts in 1988 for the Commodore 64 and Atari.


Who would have thought my number one passion when I was just 13-years-old would make such a profound impact on my life?

Well, my mom might’ve had a clue. She must have known I was totally hooked when I skipped school to skate at the mall in elementary school.

😂 I was suspended (and kicked out of the gifted program), but my time spent in the principal’s office that day is permanently ingrained in my memory. 

I'm pretty sure they put this sign up in the Shenanigans plaza because of our crew.

Fred Smith Punk Size Skateboard from 90s

That moment was a testament to how much skating meant to me. I can still remember my first board vividly — a Fred Smith Punk Size, a true OG.

In fact, I remember all of my early decks, and I rode them as they were meant to be ridden: with rails, tail covers, nose guards, and slime balls. 

You see, skating in the late 80s and 90s wasn’t just a fun after-school activity (or during school, in my case). It was an entire lifestyle.

Which skateboard did you ride in the '90s?

From Steve Caballero and the Bones Brigade to watching “The Search for Animal Chin” and idolizing Tony Hawk, I was neck-deep in skateboarding culture and wouldn’t have had it any other way. 

Search for Animal Chin Powell Peralta Skateboarding

This image is a clip from the Powell Peralta Bones Brigade skateboard video “The Search for Animal Chin”  from 1987.

I was 11 years old. The celebrity lineup was Tony Hawk,  Steve Caballero, Mike McGill, Lance Mountain and my favorite musician Tommy Guerrero. 

Are you a skater, entrepreneur or aspiring to become one?
Can I interview you on my podcast?
Email me: alex@happyprogress.com 

Today, I can say with full confidence that everything I’ve learned about success, growth, and particularly failure,
was learned through a lifetime of skateboarding. 


Life Lesson #1: Never Be Deterred by Failure 

Whenever I think about failure, I’m brought back to my 13-year-old-self attempting to ollie. If you’re unfamiliar with skateboarding, an ollie is a type of trick where both the skater and the board leap into the air. I spent days, weeks, probably even months learning to simultaneously kick the back of my board and move my front leg up to get the board off the ground. 

I bashed my shins.

Busted my toes.

Destroyed my wrists and face-planted more times than I can count.

Failure after failure, yet I persisted. This practice opened me up to landing on my face. I was so determined, I couldn’t care less about how many times I wiped out — I stood up and tried again until I mastered it. 

When I think back to this time of my life, I realize that everything I do now has evolved through skateboarding. Whenever I truly wanted to learn something new or improve my skills, I failed repeatedly until I stuck the trick. 

I apply that mindset to everything I do, from my career to podcasting, public speaking, growing and teaching. I fail until I succeed. This leads me to my next lesson, which is learning to embrace trial and error. 

Please share this on social media:


Life Lesson #2: Abide by Trial and Error 

Skateboarding lessons learned from kickflip

Once I had mastered an ollie, young Alex moved onto a kickflip. A kickflip is when you jump vertically, then use your front foot to flip your board 360° along its axis. Despite my best efforts, the kick-flip was never my most impressive trick. 

Sometimes I landed it, sometimes I didn’t. 

I wasn’t phased either way. 

I was having fun and growing.

Now, I see that today, at 44-years-old, I’m still doing the same thing. Currently, my 9 to 5 is in conversion focused web design and ecommerce. I help websites make more money by testing various things and seeing if they’ll work.

My profession is called Conversion Optimization - experimentation and personalization, if you will.

In my work, I try things over and over again, seeing what works and what doesn’t. And when something sticks, I apply more attention to ensure compound growth.

Skating was the exact same. 

From a young age, I learned to embrace trial and error and not be deterred if a trick didn’t stick. When it worked, I did it again and again until I mastered it. When it didn’t, I simply rolled with the punches. And from where I’m standing now, I couldn’t be more grateful for that mindset. 


Life Lesson #3: Explore Alternate Creative Ventures

Steve Caballero Dragon Logo from Powell Peralta

It’s no exaggeration when I say skateboarding opened me up to countless other creative ventures. From photography to web design, skateboarding culture was a source of constant inspiration. 

I’m talking about the original Fred Smith decks with the punk rocker, the Bones Brigade skeletons, Steve Caballero's Dragon and Mike McGill’s snake and skull. Graffiti and the Beastie Boys, Nirvana and Rage Against the Machine, and A Tribe Called Quest.

Everything around me was vivid and exciting and a massive inspiration. I filled sketch pads with my artwork and whenever I couldn’t figure out what to draw, I would look towards skateboarding culture. 

Between its grip tape and trucks, my skateboard was exploding with creative energy. Not only did it convince me to explore alternative creative avenues, but it also pushed me outside of my comfort zone.


Life Lesson #4: Break Out of Your Comfort Zone

warped tour skateboarding music concert

If you weren’t at Warped Tour in the 90s, you really missed out. A hub of music, good vibes, and the heart of skating culture, the Vans Warped Tour was the perfect place to meet new people. 

If you read my previous blog, How Podcasting Helped Me Overcome Self-Doubt, you’ll know I was a pretty shy, introverted kid.

With that being said, going to concerts to meet skateboarders was nerve-wracking andway outside of my comfort zone.

But I did it.

The first year the Warped Tour was headed to Ft. Lauderdale at the Edge nightclub. OMG, the EDGE!, remember that place?

...And my favorite band of all time, SUBLIME was planning to play. 

Unfortunately, SUBLIME's drummer (I think) got arrested the night before and SUBLIME never played. That totally sucked, because I was never able to see the original band for SUBLIME ever. 😢 Really sucked. But we had amazing time learning about some amazing bands like Face To Face, No Use For a Name and a little girl band called No Doubt. 

Listen to the podcast to hear more about this story.
Subscribe to Podcast

I went year after year to see some of the biggest names in skating in action, and some of my favorite bands perform live. I made some incredible friends along the way and learned an incredibly valuable lesson. 

When you care enough about something and want to grow, you’ll force yourself to break out of your comfort zone.

Today, whether I’m public speaking, podcasting, or something else that pushes me to re-evaluate what my “comfort zone” is, I remember how tough it was for teenage Alex to tackle such a huge social event like Warped Tour — and that when I really want to, I can accomplish anything.

Please share this on social media:


Life Lesson #5: Learn Your Momentum 

Half pipe vert ramp life lessons from skateboarding

Skating was a game-changer for me, but I learned the most when I was falling on my face… particularly the first time I tried to drop into a halfpipe. I was already shy and introverted. So, when I climbed to the top of the 9-foot halfpipe, I completely froze. 

After a while, I climbed back down and asked for advice. I learned that I needed to ease my way into it. So, I started pumping up and down, getting the feel for the halfpipe. Gradually I progressed higher and higher, until I thought, “You know what? I can do this.”

So I climbed back to the top.

And I sat there for a bit.

Then I finally did it. 

Of course, I fell. But I did it again and again until I was eventually able to drop in and flow through the halfpipe seamlessly. 

The trick there was learning my momentum. Today, before I embark on any task, I follow a similar route. I try it right away, and sometimes I crash and burn. But then I read books, speak with my peers, and do hours of research until I can build myself up to it again. 

I trust my own momentum to carry me through each of my goals, just like it did along with the halfpipe.


Now It’s Time for You to Drop-In 

Drop into Half pipe vert ramp life lessons from skateboarding

While I still love to skate, I’m the first to admit I’m not as adventurous on a board as I used to be — breaking a wrist at 40 is a lot more physically and financially time-consuming than it was a kid. But if you like skating, I urge you to reach out to me.

There’s a skate park right down the street and I’d love to connect with you.

Are you a skater, entrepreneur or aspiring to become one? 
Can I interview you on my podcast? 
Email me: alex@happyprogress.com 

Lastly, I'll leave you with this image my uncle made for me...

Alex Harris skateboarding in hollywood florida

Subscribe to the Happy Progress Podcast:

Happy Progress on Apple Podcasts
Happy Progress Podcast
Happy Progress Podcast on Google

Leave a comment

Comments will be approved before showing up.

Also in Personal Growth and Professional Development Blog

Bunny Young Business Therapy and Entrepreneur Advice
Bunny Young Business Therapy and Entrepreneur Advice

by Alex Harris March 16, 2021

Read More
Andy Vitale Expert Growth Advice For Designers
Andy Vitale Expert Growth Advice For Designers

by Alex Harris March 07, 2021

Read More
John Lee Dumas from Entrepreneur on Fire and Uncommon Success
John Lee Dumas from Entrepreneur on Fire and Uncommon Success

by Alex Harris February 27, 2021

Read More