Nothing is impossible! What I learned about web development from skateboarding.

First off, Happy GoSkateBoarding day 2023!! Yeah we got our own day… not that it stops us from riding every other day too. Figured this would be a good day to finally release this article after months of deliberation on the topic.

So as a skateboarder, we used to have to somewhat hide our identity in the corporate world as it used to get a bit of a bad rap. Now that it is an Olympic sport and professionals are making millions of dollars from it, it is finally getting more respect. Personally I think the Olympics were a bit a of a joke and they needed skateboarding, more than skateboarding needed them, but that’s another story.

Many of my clients know I have been skateboarding over 30 years so they often come to me with questions when their kids take interest in skateboarding and/or are consumed by it like I was. I wrote this article to share some of the lessons I have learned over the years, some correlations I see between it and web development and included some quotes from famous people to illustrate some points.

Creating something out of nothing and approach the world differently

Skateboarding changes your perspective on the world. Where others see stairs, handrails and odd shaped concrete structures, we think of possibilities of what we could do with it, which is why some consider it a bit of an art form as opposed to a sport.  Same applies to web development, if you look at all the great disruptive technologies these days like Uber, Airbnb, Skip the Dishes, etc. That ability to not just see how you have always done it, but to think outside that box is where the great apps comes from. I remember in the flash days of web development (uggggghhh), the way of doing things felt completely unnatural and adapt your way of thinking in this new realm (at the time). It was new uncharted territories for a lot of people, but I think a lot of it was just designers trying to impress other designers which is why it faded our like the pressure flip area of skateboarding in the 90’s. While highly technical, nobody really wanted to see it after a while.

“Don’t let anything poison your individuality. Break away and look in, not outward.”

Rodney Mullen

Failure is part of the game

You can’t make them all I say. Much like attempting skateboard tricks, every line of code isn’t going to be a winner but at least the only thing you will hurt is your ego. The important thing to remember is not to give up. While the pros make it look easy, the final result does not show all the attempts required.

“I’ll tell you one of the great activities is skateboarding. To learn to do a skateboard trick, how many times do you gotta get something wrong til you get it right? …And you hurt yourself, and you learn to do that trick, now you got a life lesson. Every time I see those skateboard kids, I think ‘those kids’ll be alright.”

Jerry Seinfeld talking to Chris Rock

Things are hard

Nothing great comes super easy and even the basics of skateboarding are quite difficult in comparison to some other sports. Overcoming this is extremely satisfying and teaches great resilience that can be applied to anything in life. One of my favourite skateboarders is a guy named John Cardiel, who suffered a broken back (not skateboarding) and doctors told him he would never walk again. “F@#$ you dude” was his response and he walked out of that hospital 6 months later. Same with a guy named Danny Way who broke his back surfing and made a full comeback before jumping the Great Wall of China on his skateboard.

In skateboarding we have those who have faced a harder start. People who are blind, deaf, double amputees (he recently got the cover of Thrasher Magazone), autistic, etc. as well as those who come from extreme poverty and oppression. These people embody the skateboarding spirit and their willingness to push through their challenges for this passion is inspirational to our whole community but more importantly is what it does for them. I Added a resources section at the bottom of this article with some links to some videos if you are interested in any of those stories in depth.

My point here is, web development is hard but nothing is impossible if you want it bad enough. Elon Musk created Paypal as he needed money and knew how to code. Steve Jobs started Apple out of his garage as did Jeff Bezos with Amazon. Computers are cheap now and coding only really requires a free text editor so the cost of entry is cheap to be a programmer. What you do with it is up to you.

“You just got to keep skating if that’s what you want to do, but if you don’t want to, don’t kid yourself, get out go do something else, and if it gets too scary for you, you were never meant to skate in the first place”. 

Jake Phelps. Former Editor of  Thrasher Magazine

Style & Authenticity Matters

Technically being able to perform a trick only gets you so far. It has been proven time and time again in skateboarding that it is less about the tricks you do, and more about the way you do them. Christian Hosoi was one of the great 80’s skaters (Tony Hawks rival at the time which was just marketing) and the thing that set him apart from everyone was his style. He was wearing crazy spandex, ripped up t-shirts, bandana’s, etc. and would blast airs higher than everyone. Not the most technical skateboarder, but he would blast airs to the moon.  Point is, if anyone else tried to rock that gear (and people did), it never had the same effect. He just did him and that is what made the difference.

Same goes for web development. While you can technically make something work online, if the style or user experience is not what your users want it may come up short. Good coding is more than just appealing to the ideal end user and you need to consider others perspectives too. How does a blind person use this site? How does a robot see this site? Failing to address these could be the difference between a hit or a miss.

It is okay to have you own style and sometimes it takes time to grow into it. I feel our website is now authentically me which feels really good and makes me want to write about stuff as opposed to telling people not to goto my site. Only took 20 years 🙂

“All skateboarding is putting ideas into action”

Marc Johnson

You have to commit to your craft to a certain aspect of the game

Within skateboarding, there are many different disciplines of skateboarders. Street skaters, Freestyle Skaters (dying breed), Vert skaters, Mega ramp skaters and then there are the GX1000 dudes who are in a league of their own. Some people do cross over and are good in maybe 2 areas, but my point is nobody is the best across all disciplines because each one is extremely hard and requires dedication to that aspect.  Much like web design and development as a whole, you are never going to do every aspect of it the best which is why decided to focus on our disciplines of programming and consulting.

“I think skateboarding is hugely challenging – it teaches you self-confidence, it teaches you self-motivation, and it can be something that helps you throughout your life.”

Tony Hawk

Find your place

Skateboarding is an ever shifting landscape and there are only so many people at the top in the spotlight at any given time. But it takes also takes a village. Some of the great company owners, team managers, photographers, filmers and editors in skateboarding are skateboarders too, but recognised their talent lay in different areas of the business. You can be good at skateboarding, but it takes more than just talent for the world to know. A company has to believe in you enough to pay you, take you on trips give you free stuff and hire people to film/take photos   Same goes for web development. We can’t be the best at all areas. We were okay at design, but programming was our strong suit so once we shed that design weight it was very liberating and now we can work on what we feel we are best at.

“If you skateboard, you can’t be afraid to have people laugh at you.”

Mark Gonzales

Education

Skateboarding is something you mostly have to learn yourself. Sure people can give you pointers, but at the end of the day, you are the one hucking your body around at an attempt at glory. The ones that broke down the barriers before us were never told how to do so. What if Rodney Mullen never figured out the ollie? What if Tony Hawk never landed the 900 (2.5 rotations in the air) in 1999? (so some 12 year old could come along and do the 1080 in 2012).

I would say the same goes for web development. Unless you want to understand the fundamentals of art, you can likely figure this stuff out yourself (provided you want to and are not worried about AI taking this job). Most of the legendary tech icons dropped out such as Steve Jobs (Apple), Bill Gates (Microsoft), Michael Dell (Dell), Mark Zuckerberg (Facebook/Meta), Larry Ellison (Oracle) and the list goes on.

With places like Udemy and Masterclass you can quickly and inexpensively get a taste of areas you want to get into whether it be design, coding, app development and more. They even have skateboarding Masterclasses by Tony Hawk, but the point is you have to find your niche and really want it. Good to find out quickly if this is not the class for you. I have dropped out of more online classes than I have completed because the courses gave me a good taste for the subject matter. I know I don’t want to be a photographer, video editor, app developer, 3d designer, etc. and it only cost me under a $100 per course as opposed to going through a full semester of school. It’s okay to learn things for self interest too. Not every skill has to be your career.

“Skateboarding doesn’t make you a skateboarder. Not being able to stop skateboarding make you a skateboarder.”

Lance Mountain

Community

Since html’s invention in 1992, similar to skateboarding, our community, more so than education has been fundamental to our progression. You can only teach it, once you have defined it and quantified what is happening. Skateboarding started in the late 40’s but pretty much just emulated surfing until Alan Gelfand invented the Ollie in 1978 on a ramp. In 1982 by Rodney Mullen invented the flat ground Ollie which paved the way for street skaters to get up in the air. Shortly after this, he invented the kickflip, heelflip, impossible, 360 flip and many more. While he did these tricks on a freestyle board, the community saw what was possible and began applying these tricks to street and vert.

I would say the web equivalent to this would have been in 1999 there was a company called 2Advanced who changed the way we look at the web using a product called Marcomedia Flash. They pulled off some of the most amazing animations that were quick loading (as that was more important back when you browsed the internet with a book) and had a whole new web experience. For many years it felt like Flash was an internal competition within the web industry as opposed to proving more tangible benefits to the customer. Flash was eventually sold to Adobe and ultimately died off due to not being able to be compatible with the new mobile world that evolved. So while flash died, we needed it in order to progress as it created the need for things like HTML5, JQuery, Prototype, etc.

“I’m privileged that I started some tricks, and then other people have taken it – that turned into a vocabulary for us to express ourselves. That, to me, is a living trophy.”

Rodney Mullen

 

Another co-relation in web development and skateboarding as unlike other sports we are defined more by our community, than the sport itself (i.e. Hockey, Golf, Baseball, etc) . Slalom and freestyle were some of the earlier forms of skateboarding, but died off as they were a bit more gimmicky and based off other sports (i.e. Slalom, Skiing and ballet). Longboards and snakeboards were never really accepted into the fold. Vert skateboarding lost a lot of popularity due to the easy access of street skateboarding, but still remains an area of constant progression. What is interesting about this is are not limited to what we can do with it.

Similarly, in web development have what’s known as open source and closed source code. An example of closed source code would be a windows server. It comes with hefty licenses and is maintained only by Microsoft. An example of open source code would be an operating system such as UNIX which powers at approximately 80% of the worlds servers. It is inexpensive and largely maintained by its community. While both sides, have their pros and cons, I would say that the open source has evolved much faster than the closed source.

“They’ll try to apply the rules of the day to the game – where you can’t touch your board, or you can’t step off your board, etc. And I want nothing to do with it. It’s like a game from a different planet or something, and it’s hard for me to relate to anybody who would think of skateboarding in such a narrow way.”

Mike Vallely

Resources

Here are some links to various videos. While these relate to skateboarding, they are some of the more motivational videos out there. *To note, you may hear some uhhh strong language or whatever in some of these videos (marked those ones with a star). Great content, just so you know…

Conclusion

So yeah there are some parallels between skateboarding and web development, but you will likely find those with other sports too. This article just gives me the opportunity to share the correlations I have seen between two of my passions and hopefully can provide some inspiration to somebody in someway.

Depending on who you are there are different takeaways from this article…

  • If you are a programmer/designer/content creator/etc., is this really what you want to do? If not, find that thing.
  • If you are a skateboarder, use that attitude to other aspects of your life. Bro, you gotta know if you ain’t gonna be pro so know when to switch gears career wise.
  • If you are a parent of a skateboarder, support their decision to do this (cause they are going to do it anyway) and if they are young, make them wear a helmet (sorry kids).
  • If you are a city councillor, please fund your local skatepark.

Hope you enjoyed this article. Thanks for reading!

Simon McCaffrey

Simon has been building software for Canadian businesses for 27 years, from Toronto, on too much coffee. He wires AI into how businesses actually run, and tells you when it is not worth it yet.