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Ever been culpable of rolling an idea up a hill beyond its use-by date? Even with the benefit of hindsight, it can be kinda difficult to spot the optimal moment when it would have been wise to let go. Which is why this ‘fail fast’ fad has me flummoxed. I’d hoped that I could apply it to experience and not repeat the mistakes of the past, but I’ve been struggling to understand what it actually means.

See, I first took it that decisions to abandon a project can be accelerated. The lean model talks about testing your hypotheses and quitting as soon as they fail. So failing fast becomes about setting specific and measurable benchmarks that trigger the escape hatch if they are not met.

A problem with this is that benchmarks may not be simple to define and can be harder to measure – particularly where the concepts are emergent. For example, how do you define a benchmark to filter out the positive responses in market testing that, combined with a little confirmation bias and a dash of inertia, provide more than enough motivation to keep going.

Another assumption is that you can save money, time and effort by stopping out of failures early. But as any trader will tell you, a stop-loss can quickly become a target that simply gets triggered before the bigger trend resumes. The last thing you need if you are committed to a project is to exit just before the opportunity can be made real.


A plan, like a tree, must have branches – if it is to bear fruit. A plan with a single aim is apt to prove a barren pole. – Basil Liddell Hart, 1954

Perhaps the point then is that it is more important to get the big picture right – the big trend that will ultimately underpin the market dynamics that can support success. It’s like the difference between losing a battle and a war.

The genius of Winston Churchill was his ability to filter the chaos through the big picture, so that decisions were optimised for the very uncertain circumstances. “There must be that all-embracing view which presents the beginning and the end, the whole and each part, as one instantaneous impression retentively and untiringly held in the mind.” He had a framework within which to respond to challenges and take advantage of opportunities as they arose. Individual failures are simply events that help to shape the direction taken to achieve the ultimate objective.

David Einhorn likens the challenge to playing poker – where there are things that you know with certainty (your cards, everyone’s wagers), things you can surmise (that fellow’s playing style) and things that you don’t know except at the limits (the number of cards still to be played). There’s a spectrum of uncertainty along which calls are made. The challenge is to identify the key calls, those decisions that will make the biggest difference to the outcome – and tilt the odds in your favour. Again, it’s his ability to assess the context and then the circumstances within that determine the appropriate choices. Failing fast may mean folding early on a hand, but in doing so you’re more likely to have the resources to bet big when the opportunity arises.

So perhaps failing fast is a really a short-term concept within a long term context. And just as “a plan doesn’t survive first contact”, it’s understanding the potential points of failure and being aware of the contingent paths that will optimise chances of success. If failing fast is a skill, it is referring to the ability to dynamically choose the path not the destination. The objective remains to scale the hill, just that it may require pivoting along a few paths to get there. Even Sysiphus can have his good days when it’s as much about the journey as the destination.