When I tell people that I still skateboard regularly, they are often surprised as tech geeks and hard-core skaters are groups that don’t usually overlap. It’s been my passion since childhood and by skating I don’t mean nice, clean cruising on a longboard but rather street spots, skateparks, tricks, falls and getting kicked out of places by security guards.
The way I see it, skateboarding is to entrepreneurship what team sports are to corporate careers. A childhood activity that teaches you the basics required to perform professional tasks.
Here are some of the most important lessons I learned while skating that any entrepreneur should know:

1. There are no rulebooks and no one to ask permission from
   Most school systems and group sports teach us as kids that life is a unidirectional path created by the hops between pre-defined points (think grades, belt colors, leagues). Each point is regulated by a relevant authority that determines who graduates each point, eventually leading to the end certification. Incentives and punishments are in place to move people in the desired pace and direction.
   Skateboarding (among other “street sports” like BMX or Roller-blading) has no classes, no coaches, no certificates and hardly any organized competitions. At any given point, you learn from your peers or by looking at videos and magazines. You realize very fast that it’s only up to you to show up, practice and progress. No coach to tell you what to do, motivate you or punish you when you stray.
   Being an entrepreneur is very much alike; the hardest thing for people to deal with is the fact that there is no one to tell you that your idea is good and it will work or in other words, someone to ask permission from. At the same time, no school system exists to certify that you are indeed “best of class” in entrepreneurship. Only results matter.
2. If you are not falling and hurting, you are not trying and not learning new stuff
   There are days when you are lazy, you don’t feel like stepping outside your comfort zone, you just try the same tricks you have practiced and mastered already and you land them all perfectly. When you get home though, you feel bad, the lack of pain tells you only one thing, you haven’t learned any new tricks. Entrepreneurship is the same, failure hurts big time because it’s so visible and directly tied to you. There is only one way to avoid the risk of pain and that is not trying something new. Once you associate failure and pain with progress, you fear less in general and feel more content when you do fail.
3. Some of the best tricks, you learn by mistake while trying something else all together
   In spite of misperception that every successful company is a result of a well thought plan that is perfectly executed kind of like an Olympic trainer’s career in China, the reality is that you learn one thing while trying something else all together. When trying a trick over and over again without success, it’s important to take a break, move to another trick only to figure out what you were doing wrong in the first trick and land it. Entrepreneurship is not a serial process but a parallel one in which a few balls are up in the air and you never know which one will work out best for you.
4. Competition is beneficial and no competition is a warning sign
   Learning a new trick that none of your peers has yet to land is nice but exponentially harder than being the second guy landing it. If you are learning a trick and no one else is showing interest, you know it’s either been done and everyone is tired of it by now or a trick that might not be feasible given current means/conditions. In entrepreneurship, much is the same. Instead of worrying about competition, you should worry about lack of competition. Instead of worrying about first movers’ advantage, you should appreciate a second movers’ efficiency.
5. You have to commit to the trick, most painful falls are due to “bailing” in mid-air
   It’s hard to believe it but some of the most painful falls are when you start a trick without the conviction to land it no matter what. Yoda’s rule applies here “do or do not, there is no try” which might be confusing but makes sense once you realize how often people start things without the conviction to do what it takes to bring it to completion. Start-ups are no different, a very large percentage of failure I see around me are due to the entrepreneur giving up and not because failure has been proven.

As kids and later through our lives, we all take part in organized sports and the more suburban the area we grow up in, the more structured our play is. I recommend finding the time to experiment more with “Street” and “extreme” sports and enjoy that wonderful view outside the box.