Loop Chicago


Gabe Klein: Don’t Be Afraid to Screw Up and Learn

Join me at Chicago Loop Alliance’s Annual Meeting this Thursday where I’ll talk about the power of public-private partnerships as well as urban policy and transportation innovation.  Until then, enjoy this excerpt from my new book:

Coming from the start-up world, the idea that I was supposed to be risk averse and instinctively say “no” made no intuitive sense to me. I was taught to iterate and fail fast as a survival instinct in business. We never would have ended up with convertibles or pickup trucks at Zipcar without this philosophy. In the start-up world, “failure is not only invoked, but celebrated.”1 This has been a basic tenet of technology startups for decades. In Walter Isaacson’s book on Steve Jobs, he tells the story of the iPhone launch event, where the thing literally did not work and was sporadic at best, an amalgam of iPod, phone, and computer, with nothing quite functioning as it should, even minutes before the event. Jobs held the unveiling anyway, and miraculously, when he made that first call from the stage, it went through. If he had given up because the product at that time was unreliable and a borderline failure, where would Apple be now?

So I set the expectation that we were going to experiment, make mistakes, and then make more responsible long-term decisions for the taxpayers as a result. This became the new modus operandi and freed up our teams to take risks.

Richard Branson, in his autobiography, Losing My Virginity, tells a great story about the redesign of the interior of the Virgin Atlantic fleet in the 1990s. When Virgin started installing the new interiors on the planes, a host of design problems surfaced, the sum of which cost Virgin millions of dollars as they struggled to salvage the overhaul. However, instead of firing the designer responsible for the snafu, Branson did just the opposite. He asked the same person to design the interior again, and this time, to succeed and prove himself. The designer did just that, and the resulting interior proved to be a seminal, award-winning design, as well as one that could have been carried out only by an eternally grateful, loyal employee hell-bent on salvaging his own reputation.

You need to push boundaries and undermine the status quo, or your work reverts to the codes, regulations, and standards that have become the caricature of bureaucracies. What’s worse is that these standards often fail us, as they did in this instance, because they fail to encapsulate the dynamism of the city, the potential for engineers to creatively solve new problems, and the capacity of our citizens to see and embrace change.

When you attend CLA’s event you’ll get a copy of my book; and we can have a quick chat while I sign it for you!


1 Rory Carroll, “Silicon Valley’s culture of failure… and ‘the walking dead’ it leaves behind,” The Guardian, June 28, 2014; http://www.theguardian.com/technology/2014/jun/28/silicon-valley-startup-failure-culture-success-myth

Start-Up City: Inspiring Private and Public Entrepreneurship, Getting Projects Done, and Having Fun

Gabe Klein with David Vega-Barachowitz

© Island Press


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