Having failed a few times, I claim I know what it means.
Knowing failure means a few things.
First, it means that I know that there are degrees of failure. There is indeed that complete, catastrophic failure - the end - that most people think about when they think of failing. But the actual experience of failure teaches you that it can be far more gentle, and indeed reversible. Having failed, therefore, means many bad things but one redeeming one - overcoming the fear of failing.
Second, the experience of failure also teaches one to plan for failure. This is a departure both from the failure-as-catastrophe view of the world (in which case, no plan is really enough) and also the bravado of not thinking about failure. Indeed, this is not planning to fail, but planning for failure, so that if and when it comes, one has a Plan B in hand.
Third, failing leads to an optimistic view. This does not mean failure is nice - it is never so when you tried something that did not work - but that the realisation that failure may be unavoidable but it is not irreversible is rather liberating. This may lead to other good things. Like, one may fail, but it does not have to all go to waste - and one may derive a number of lessons from such experience.
Indeed, I talk about me as I write these things. I tried to create an enterprise which did not work, and I ended up spending two years on it, incurring debt and going nowhere in the end. But this was not the first time I have failed and I was quite prepared for it. I had a plan, which meant compromises and a tactical retreat but not catastrophe, which I fell back on eventually. This failure became my Business School, something I did not go to, with similar implications on my bank balances and hopefully enhancing my abilities.
What makes failure worthwhile, I shall claim, is not the fact of failure itself, but what you do with it. My two years of setting up the business have given me an extraordinary range of experiences, of sales, marketing, finance, technology and people management. It did burn me out and therefore, the tactical retreat of taking on a more junior role was helpful - a year was enough to get back my bearings! But now I feel more ready to start again, and more equipped to make things work. And, this is possible because I have thought about the failure all the time through the last year, thinking about what errors of judgement I have made (there were several) and what I would do differently if I start again now. This was all connected - accepting failure as normal and not thinking it is my destiny to fail, and yet, accepting the mistakes I have made and regaining the appetite to try again.
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