I'm a great believer in failing - thankfully, since it happens to me often enough. In the same vein, I believe that one learns from one's mistakes, not from one's dumb-stupid-baka errors. Making mistakes is the only way to deal with uncertainty (as the alternative is do nothing). Errors occur when you ignore something fairly certain, but that you haven't seen (or wanted to look at).
Failing well is essential to moving forward in an increasing uncertain and unpredictable work environment. In the past ten years, everything from technology, to footprint, to jobs is changing. Planning is all very well when we can forecast with some degree of confidence, but to keep planning when we know the plan is wrong is a little bit weird, not to say dangerous. So how to fail well?
- Don't do anything stupid: there is enough uncertainty going around not to try and do something radical and different in a known area. A few years ago I found myself on a beach in Brazil, in what was the middle of the winter for me in Europe. I thought, what the hell, and I went for a swim, got carried away by the undertow and saved by the baywatch. Embarrassing - I really had a moment thinking "this is it, goodbye." Now, that was really stupid. They were SIGNS telling to watch out. Ignoring gravity, demographics, or expertise is not innovative, it's just plain dumb.
- Start with what is at hand and fail quickly: don't think it through, just do something with what you've got! Thinking about it usually complicated matters with all sorts of unlikely scenarios. The point of doing rather than thinking is to explore. We now have many opportunities to do things virtually, so it's pretty low cost to get something done - respecting rule number one: don't do anything dumb that would bankrupt you or take unreasonable risks.
- Rope in others right away: don't fail alone if you can help it. By collaborating intensely with two or three people, chances of success increase dramatically. The questions is often to find the right people and to get them to participate to whatever nonsensical idea you're about, but several heads are definitely better than one.
- Change your mind often: the point of doing is learning, not succeeding. Failing is useful only if you do learn, which means changing your mind and abandoning your original plans to follow where the experiments and your team mates lead. We're not wired to find changing our minds easy, so we need to learn to appreciate every time it happens.
- When it works, do it again: I have a great friend who is a movie producer and explains Hollywood thus: no one ever knows the recipe to what works, so as long as people pay to see a movie, keep doing sequels, which is the way you build a franchise… until audiences get bored for it. The flip side to an open mind is to be disciplined about repeating what works without chasing something else and building it further with the tools at hand.
Over the years I've notice that many things I have failed at (I mean, really failed, as in not getting the job, not getting the funding, etc.) have closed some doors but more importantly opened others which did succeed. The question then, in a turbulent , uncertain world, is how to work at opening doors that you can't see are there. The only way I know is to try it and fail... until it succeeds.