Okay, so let’s start by agreeing none of us like to fail. It’s in our cells. Our genes want to get as far down the evolutionary ladder as possible, and there are plenty of much more immediate ways we want to succeed. But could it be possible that our relationship with failure is stopping us dealing with some of the biggest problems of our time?

That’s @critter‘s fail whale tattoo. Fail whale would be very familiar if you were using Twitter early on – it flashed up every time the website timed out.

It was designed by Yiying Lu (originally “Lifting Up A Dreamer”), and I’m chatting with her tomorrow. So every time Twitter failed, Yiying’s artwork flashed up in front of a ballooning groups of ‘tweeps’. So failing is clearly something Yiying has a mixed relationship with. From what I gather, she doesn’t have a significant base of failure to draw on. But she has Twitter’s turbulent path from buzzed online curiosity to news-breaking social media platform to thank for a serendipitous rush of international exposure.

Anyway, Yiying’s also dabbled in lecturing. Teaching design students at the University of Technology, Sydney. And when I said I was super interested in failure and her mixed experiences with it, she sent several vollies of link-filled emails as required reading.

Yiying pulled this quote from a spectacular speech by author JK Rowling.

It is impossible to live without failing at something, unless you live so cautiously that you might as well not have lived at all – in which case, you fail by default.

That seems intuitively true. In my experience, failing is a good sign you’re trying something new. But Rowling went far deeper, explaining how crucial failing was to her phenomenal success.

So why do I talk about the benefits of failure? Simply because failure meant a stripping away of the inessential. I stopped pretending to myself that I was anything other than what I was, and began to direct all my energy into finishing the only work that mattered to me. Had I really succeeded at anything else, I might never have found the determination to succeed in the one arena I believed I truly belonged. I was set free, because my greatest fear had been realised, and I was still alive, and I still had a daughter whom I adored, and I had an old typewriter and a big idea. And so rock bottom became the solid foundation on which I rebuilt my life.

It’s just the kind of mythologising that works in a graduation speech, and Rowling was speaking to a graduating group of Harvard students. But what makes it inspiring listening is that it’s borne out in Rowling’s story. She had to fail to get where she did.

Yiying also sent  a couple of interviews she had done – a good overview of the fail whale story in Failure magazine (of course), and another in the New York Times Magazine’s Consumed column.

One of the things I find interesting about failure is how it can be a doorway to some great inspiration that social taboos (“that’s wrong!”) or intellectual rigidity (“that’s ridiculous!”) would veto.

Most worrying, is the risk that a fear of failure will stop people solving ‘wicked problems’.

Wicked problems have these features: It is hard to say what the problem is, to define it clearly or to tell where it stops and starts. There is no “right” way to view the problem, no definitive formulation. The way it’s framed will change what the solution appears to be. Someone can always say that the problem is just a symptom of another problem and that someone will not be wrong. There are many stakeholders, all with their own frames, which they tend to see as exclusively correct. Ask what the problem is and you will get a different answer from each. The problem is inter-connected to a lot of other problems; pulling them apart is almost impossible.

That definition’s from a great piece by New York University media researcher/commentator Jay Rosen.

It gets worse. Every wicked problem is unique, so in a sense there is no prior art and solving one won’t help you with the others. No one has “the right to be wrong,” meaning enough legitimacy and stakeholder support to try stuff that will almost certainly fail, at first. Instead failure is savaged, and the trier is deemed unsuitable for another try. The problem keeps changing on us. It is never definitely resolved. Instead, we just run out of patience, or time, or money. It’s not possible to understand the problem first, then solve it. Rather, attempts to solve it reveal further dimensions of the problem. (Which is the secret of success for people who are “good” at wicked problems.)

That is key: “Failure is savaged, and the trier is deemed unsuitable for another try.”

Dealing with complex problems, we need to experiment, take risks, and not be afraid of stepping away from incremental development. And that’s going to take a very different relationship with failure.