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The Wicked Company

Shut up and Skate! — How to fail sustainably

I have done many things in my life, but I never thought that my skateboarding would provide value to my business consulting. Skateboarding is an innovative, amazingly complex and accurate activity. Considered an extreme sport, what is the connection between this sport and the future of organisations?

It is the embrace and inclusion of failure into its culture. If you watch any skateboard competition, failure does not seem to play a big part when those athletes perform amazing stunts with ease. The same is true when you use a Google or Uber service feature. But that is the similarity worth understanding.

Last week, I was talking to Geoff Colvin, author of ‘Talent is Overrated’ on our ‘The Wicked Podcast’ podcast. The idea of deliberate practice played nicely into some stories I had from the history of skateboarding.

Failure is 99% of your skateboarding activity. It is so extensive that the sport has two words for failure. BAIL, which means a controlled failure or you might think of it as a sustainable failure and SLAM, which is an uncontrolled or catastrophic failure. If failure is everywhere every day and success so slim, why does anyone bother to skate? And if we HAVE to fail, how can we make sure the majority of our failures are sustainable and not catastrophic ones?

Here are some factors:

  • People support each other when failure happens instead of taking each other down (safe space)
  • Stories of failure are shared either as word-of-mouth or in skate videos and at competitions (feedback and sharing)
  • Experimenting and practice are values. If you experiment harder than anyone, you are considered successful and valuable. Experiments are included in communication and content, like videos. (celebrate, emphasise)

These factors can and should be implemented in organisations. They directly enable what some people call a growth mindset. Below are some examples and how they could translate.

How much failure is still a success?

Rodney Mullen has trained more than 10,000 hours and invented most of the modern skateboard tricks; many never been mastered by others. Jonny Giger has a youtube series, where he tries to master EVERY trick Rodney Mullen has ever done. His videos are 10min+, and they are mainly failure(it’s worth watching the full 12 minutes below). He has over 500,000 views on most of them. He has a sponsor and a pro deck.

It is fascinating to watch someone trying to achieve excellence and how they get there. There is learning in understanding how big the challenge is and how to get there.

It’s worth watching the 12 minutes that span 2–3 days of constant experimenting for success.

Scaling up from 5 to 100 experiments is what sustainable success looks like, not funding that one big innovation idea!

Organisations can learn from this. Failure should be documented, shared and gain positive feedback. Hiding failure is hiding value. I have worked with numerous large organisations who wanted to fix bad investments that had burnt millions with no benefit created. Sometimes the outcome had even damaged the brand or the customer experience, making the company lose revenue and customers on top of losing the investment.

It is smart to investigate why things fail and then communicate and action improvements. If the website gone live just failed, there is likely an organisational reason for this. Building a new one with the same people and process in place is insanity (according to Einstein).

Try asking: Yes, but what have we learned?

Not telling the new people in detail what went wrong and why will only result in them repeating the same mistakes.


  • Document the failure
  • Collect insights on why it failed
  • Make it accessible around the organisation as a learning
  • Onboard the new team to avoid the mistakes to be repeated
  • Please enable them to drive the actions to improve
  • Make it the organisation’s responsibility to support the actions to happen

The communication part is the most missed aspect of this. Depending on the size of your organisation, it is valuable to consider a ResearchOps layer that is a central point for sharing information.

Communication rarely travels beyond departments, which is another trick missed in avoiding mistakes to be repeated. Building horizontal layers or inclusive tribes can help.

Skateboarding has included fail reels in their skateboarding videos, which since have been populating youtube. Yes, skateboard companies go out there and add their professional skaters failing on tricks as part of their communication and brand. How ‘gnarly!’.

Below: Chris Cole’s Battle Scars (skateboard slam series) WARNING: not for the faint of heart

Support Variants

Experimentation is significant in skateboarding. In business, it has been reduced since Six Sigma arrived and removed variants in favour of efficiency. This is not a good strategy anymore. Trying new things should become part of your DNA. In skateboarding, there is a culture of sponsors paying skateboarders to try harder tricks and paying them for it. There is a famous story about Chris Cole being paid to do a massive trick at his local spot, and he landed it on the first attempt and got paid $100 for it.

It is an example of small investments to push boundaries and test things. Organisations should be able to do that a lot.

The other aspect of variants is the nature in which the most innovative skateboarders learn. This is very similar if not identical to what Geoff Colvin describes happens when you do deliberate practice. Rodney Mullen, whom I mentioned earlier, describes his process in detail in one of the videos about his innovation process. He deconstructs a new trick into its smallest parts and then experiments with that part. Til it is stable enough to do the next part. Then he stacks it up and voila, innovation!

You finally pack all that stuff for granted and you forget about it, and you are focussing only on one aspect, where my eye and where my back shoulder is when I see the edge of the table and then everything else is taken for granted and runs on auto-pilot. — Rodney Mullen

Organisations can do the same thing:

  • Sponsor many small things instead of a few big ones (can you assign budgets like that?)
  • Give people the time to break things down and improve them; innovation does not grow in massive steps (MVP and sub-MVP)
  • Variants beat efficiency. Every variant you can test will help you understand a problem better.

When I was talking to management uber-guru Tom Peters, one of the best leadership characteristics he mentioned was the ability to move on after a failure positively. The best performing companies run over 1,000 experiments every year.

The payoff for you? Defying the laws of physics maybe:

Iterative Words

Last year, no one was talking about wicked problems or that moving targets are the new norm for organisations.

This year, every rulebook just flew out the window.

This is new, which means we will have a lot of failures along the way. The modern world is just not known enough to us.

As an organisation, embracing sustainable failure and avoiding catastrophic failure can help significantly to step forward more confidently. And it is worth to look at how others have embraced failure and translate it to fit our capabilities.

Sustainable failure equals Resilience.

Please feel free to ask me anything about the above ways to embrace failure about the challenges you see to implement the above.

Do you disagree? What are your hurdles to become a Wicked Company?

Exciting times ahead!

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Marcus Kirsch

Marcus Kirsch

Innovation, Service Design & Transformation specialist. Keynote speaker and author. Opinions are my own.