Scott Adams has long been a hero of mine with his insight into corporate life. One of the things that appealed to me when I first started working at Microsoft years ago was that while I recognized a number of the dysfunctional characters and behaviours from previous roles, but I then couldn’t imagine Dilbert scenarios playing out in Microsoft offices (as Microsoft has grown in size and complexity, maybe the cartoons provoke more than a self-recognizing giggle from time to time these days).
His latest book ‘Stick to Drawing Cartoons, Monkey Brains’ publishes a range of his blog posts from recent years which cover a broad range of commentary and reflection. One of the recurring themes in talking about his own experience is the power of embracing failure…
“First, allow me to confess that I have failed at 90 percent of the things I have ever attempted. Failure rarely bothers me. I always learn something in the process, and the screwups provide a nice backdrop of humility for the few times when things work out.”
“To put all of this in context, I remind you again that I fail miserably about ten times for every one success. (That’s an accurate estimate. I’ve literally kept score.) The failures always involved activities for which I was completely unqualified. Ironically, I couldn’t even ‘keep my day job.’ On the other hand, my successes have all been in areas in which I had no obviously relevant background or experience whatsoever. I know that many will say I shouldn’t have written this non-Dilbert book, especially since it isn’t about business. Non-Dilbert books are not my area of expertise. ‘Stick to drawing comics’ is the advice I will hear more times that I care to count. You might be thinking it already. I’m used to it. If I had listened to that sort of advice in the past, I would never have done anything interesting in my life, much less be successful. Was it smart to write this sort of book, or will it turn out to be another in a long list of my failures and embarrassments. Beats me.”
“While I’ve had some notable successes, the vast majority of things I’ve attempted have been flops. But I shake them off and keep on plugging. I always learn something from the flops that helps me later. For example, failing at my corporate career made me a better cartoonist.”
His chapter ‘Lights Out’ tells the tale of doing a ‘keynote speech’ for a big event (which earns him a big fee and is a huge step outside his comfort zone) where everything just fell apart:
“I was standing in front of a corporate group, a few minutes into my keynote address, when the lights went out. The lights returned in a few seconds, but the power surge fried the AV equipment. My professional keynote speech, of which 75 percent involves showing comics and telling stories about them, was dead on arrival. As it became clear to the assembled executives that the equipment wasn’t going to work, they looked at me with what I can only assume was a mixture of pity and ‘glad it’s not me.’ Researchers say that public speaking is one of the great fears in life. But what if you have no speech and you’re already in front of the crowd? That’s gotta be worse. But I didn’t feel fear. I’m not wired in that way. I felt amused. This was something new. I like a challenge.”
He goes on to describe how he made a few quips, turned the session into a Q&A and steered difficult (and boring) questions into more interesting areas. In the end, he concluded “It was the most fun I’ve ever had giving a speech. I feel most alive when things go wrong and routine gives way to emotion. With any luck, something will go wrong today, too. I sure hope so.”
He has a chapter called “Knowing When to Quit” (“Quitting is underrated.”). “So how do you know when to ail out of a losing idea? I heard a useful rule about predicting success during my (failed) attempt at creating a hit Dilbert TV show…If everyone exposed to the product likes it, the product will not succeed…The reason that a product ‘everyone likes’ will fail is because no one ‘loves’ it. The only thing that predicts success is passion, even if only 10 percent of the consumers have it.”
He also concludes the chapter with, “If you plan to try ten things knowing that nine will fail, it’s a good idea to pursue ventures that won’t kill you if they fail. I prefer challenges where the worst-case scenario is that I’m embarrassed or tired, as opposed to bankrupt or dead. And I prefer challenges where the upside potential is unlimited even if unlikely. But those are personal choices. I find it easy to shrug off failure, so failing 90 percent of the time works for me. Your mileage may vary.”
Finally, “Creativity is allowing yourself to make mistakes. Art is knowing which ones to keep.”
Leadership and Management / Turning Adversity to Advantage 
I a time when I worked at Sun when we were not allowed to toalk of problems, only opportunities. My manager at the time was a very plain speaking man who could not quite grasp this Californian way of thinking. In one meeting after we had been discussing an issue for a while he uttered the memorable like: "I think what we have here is an Insurmountable Opportunity."A wonder man I learned so much ftom – and of course one of those lessons was being allowed to fail. Sadly no longer with us though. http://blogs.sun.com/pgdh/entry/roy_chadowitz_1955_2005