I often speak about “Freedom to Fail” as an essential element of success for all sizes of systems and processes such as a hackathons, ecosystems, corporate cultures, and art. Freedom to fail isn’t just about innovation and creativity, it is also about resilience — small failures teach you about what to be careful about in the future to avoid big failures.

If you look at the success of Twitter, at its root was a failure. Many other big “successes” started with a failure. When my first business went bankrupt, a long-time entrepreneurial friend told “NOW, you are truly an entrepreneur.”. He was right — I can still fear failure, but I also know I minimize its danger, and I can survive & learn to thrive from it.

There are a variety of ways to do encourage Freedom to Fail. For instance, at iOSDevCamp we celebrate “Best Sacrifice to the Demo Gods” with one of our best prizes for this reason. It is also an important element of my teaching pedagogy in my MBA classes, where I teach the related ideas “Perfection is the Enemy of the Good”, “Fail Fast”, and “Ship Early and Often” throughout the course.

My biggest success, SSL, came from studying the failure of my previous groupware product which failed because people didn’t trust it. So I had to learn about the fundamental nature of trust, which put me in the position to create the world’s dominate encryption security standard. Google reported today that 65 percent of all outbound email traffic is now secured by SSL, and 50% inbound, something that was not anyone eyes back in the day which was focused only on using encryption for internet commerce. Back then I saw the failure of PGP & S/MIME to broadly secure email could be pragmatically improved, albeit imperfectly, by also using SSL for securing other things than it was intended for, so I used my authority as standards editor to reserve the scarce resource known as TCP ports for use by SSL in addition to SSLs expected use. I got a lot of flack for that, but the proof that it was the right ideas now is in the growing pragmatic ubiquity of SSL to secure SMTP, IMAP & POP protocol pipes that email travels through. With this success, it is now easier to take other steps toward improving security to achieve the full 100%.

The always good Freakonomics Radio podcast discusses Freedom to Fail in their latest podcast “Failure is Your Friend”. it suggests techniques such as a pre-mortem, where you gather team members to image a failure in the future, and learn from this imagineering. With this “Prospective-Hindsight” then you can design to avoid many that failure. It works because everyone is asked to “fail” and the fear of failure or talking about failure is socially more acceptable. Closely related, I also recommend last week’s repeat podcast on the topic of “The Upside of Quitting”.

ABSTRACT: “In which we argue that failure should not only be tolerated but celebrated.”

Freedom to Fail & Freakonomics podcast “Failure is Your Friend”

Life With Alacrity

© Christopher Allen