Fail Fast, Fail Often

Fail Fast, Fail Often

Lately I’ve been preparing for a presentation where I will talk about the topic ‘Fail Fast, Fail Often’.…  It’s not a topic I usually talk about, but as an entrepreneur I’ve had my share of ‘failures’ or as I like to call them ‘perceived failures’ as they are after all only a failure if you perceive them as such, so I’m happy to be brutally honest and use the opportunity to do some soul searching and give me spin on this often talked about topic.

The first conclusion I came to is that we’ve all been there. Confused. Tired . FEELING.LIKE.WE’VE.FAILED. It’s an awful feeling.

But probably even worse is being worried that we might fail before we set out to do something and not even getting started.

Imagine the potential fear of failing a young Frenchman by the name of Philippe Petit would have felt when in 1974 he decided to catch the attention of jaded New Yorkers by wire-walking between the twin towers of the World Trade Center.

People in the street gasped at the sight 1,350 feet up, and the photo and film coverage of the seemingly spontaneous event was extensive enough that this ultimate high-wire act went 1974’s version of viral. The act was deemed ‘the artistic crime of the century’, and has since been commemorated in James Marsh’s 2008 Oscar-winning documentary Man on Wire, and The Walk, an IMAX 3D feature film directed by Robert Zemeckis and starring Joseph Gordon-Levitt as Petit.

The World Trade Center was not Philippe Petit’s first high-wire conquest. A magician from the age of six and former street juggler, Petit began training on the wire as a teenager. In 1971, his first big public (and illegal) wire walk was between the towers of Notre-Dame Cathedral in Paris. His next came in 1973, when he walked between the pylons of the enormous steel arch Sydney Harbour Bridge in Australia. Perhaps these were just warm-ups for the big event, since Petit traces his obsession to an article he read about the World Trade Center in 1968, during construction of the twin towers.

Did Petit fear failure? The consequences of him failing were certainly pretty severe.…  Needless to say, there were no safety nets or harnesses in place.

But what is failure anyway?

The first person I thought of when I thought of failure (or perceived failure) was our good old friend Homer Simpson and his regular exclamations of ‘Doh!’ Homer often feels like a failure. Why?

  • Fear of being judged by others/what others will think? (Flanders, his god-following neighbour)
  • Fear of missing out (FOMO) – What he missed at Mo’s Tavern that his mates got to enjoy
  • Fear of not being able to do something you set out to do (numerous episodes and examples)

In short, fear is often at the centre of our concerns around the concept of failure (or perceived failure).

I have always loved this quote and believe it to be true:


Do you?

On a lighter note, what do you think of this thought?


In Silicon Valley “fail fast, fail often” is an often heard mantra.

How do I know this? In 2013 I spent a couple of weeks there. I’ve blogged about this trip in the past, and also ran a webinar where I completely unpacked the trip. You can watch that here.

But in the context of this blog post on Failing Fast, and Failing Often, it’s suffice to say that borrowing stacks of cash, and ‘failing’ or having a business be perceived as failing appears to be perfectly acceptable there. There is even an event called FailCon which has been running for a few years now, where startups and established businesses talk openly and honestly about their Fails.

There is also a global phenomenon called ‘f*** up’ nights which started in Mexico City, in 2012. F***up Nights now take place in more than seventy cities in twenty-six countries around the world where entrepreneurs share their failures. Cool huh?


The short of it is, the path to success is not straight forward. And it’s not smooth. And it’s not easy. Trust me I know.

On most days I go through an iterative process such as this:

In fact it’s perfectly normal! It’s how creativity and innovation, two things our company places a great value on occur.

You simply have to push the boundaries!

So ask yourself and your team this very important question.



There’s a few questions you can ask off this question to dig a little deeper including:


  1. Can we give cudos to those who try to break things/fail/innovate/iterate?
  2. What is the worst thing that can happen?
  3. Can we give cudos to those who keep trying, keep failing, and eventually succeed?
  4. What are all the ways we can do it wrong before we do?
  5. How can we find success through failure?
  6. Failure is a matter of perspective – what is our perspective of failure?
  7. How do we redefine failure at our organisation?
  8. When a project has failure written all over it what do we do?
  9. Can failure be an agenda item on our meetings? To encourage healthy discussion on what went wrong and for us to learn from the experience and/or workshop and turn into positives?

At the end of the day, the key message I will be sharing is that “failure is only such, if you consider it such & each‘failure’ is inching you towards success” and that there are “secret opportunities hidden inside every failure”.

What is your thoughts on failure? Is it something we should be talking about more often? Is it an opportunity to learn from? Should we fail fast and fail often?