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The value of failing upwards

20th May 2022
failing into bankruptcy

“I have not failed. I’ve just found 10,000 ways that won’t work.”

Thomas Edison

Failing stings; there’s no doubt about it.

Whether it’s a failed test in school or a failed business in adulthood, failure is never a pleasant experience. Often it leaves us uncertain of our future or can make us question our abilities. For many, failure is the end of the road towards whatever it is they’re pursuing. Whilst understandable, this is certainly not a mentality I try to encourage in others.

On the other hand, there is a small cadre of those who choose to push past failure – to grit their teeth, dust themselves down and pick up the challenge again. Throughout history, there have been scores of men and women who have refused to be beaten by failure and adversity, and who have seen failure as something to overcome and ignore. However, I don’t necessarily subscribe to this viewpoint either. In fact, I see failure as something quite the opposite.

Over the course of my life, I have come to see failure a little differently. I see failure as something that can bring positive change. Not just for the failing party in question, but for everyone involved. I know this may sound counterintuitive, but bear with me on this.


I’m not the only one to have come to this realisation. Silicon Valley in America has been vocal about the ‘fail fast’ mentality that companies have grown to adopt; one which encourages firms to try innovative and disruptive new approaches, and to focus on the rewards – risks are encouraged, but must be calculated.

Both Elon Musk and Jeff Bezos – perhaps two of the most successful men on the planet – have reiterated their belief in the importance of failure. Musk has delivered several speeches on his rate of success/failures, arguing that without his countless failed projects he would never have experienced the success that he has now attained. Bezos, meanwhile, has strived to make his conglomerate “the best possible company to fail in”, arguing that a company that encourages its workers to try, fail, and try again, is a company that will nurture resilience and innovation.

Failure is becoming fashionable. It’s gone from being a dreaded outcome or a badge of shame to being considered the fast track to experience and growth. In years gone by, if someone made a mistake costing their firm thousands of pounds they may have been fired on the spot. Nowadays people have come to realise the error of that way of thinking. Why would you fire an employee that just gained valuable experience and knowledge on how to never make that mistake again?

Failure is something I’m intimately acquainted with. When my first company (Essex Air Conditioning) collapsed, I learned a slew of lessons. These ranged from how to balance my interests with my income, to how to pick myself up after a hard loss and avoid failure in the future. Without the lessons I was taught by my greatest failure, it’s doubtful that I’d ever have had the insight and experience required to grow my second company Cloudfm to the heights that it’s reached today – far surpassing the success of my initial firm.


Ok Jeff” I hear you say, “I get it – failure builds experience. I watched chitty-chitty-bang-bang too, you know” and whilst yes, that is a key part of my argument, it’s not the only part.

Failure can be a great teacher – but it can also be a motivator, it can be a source of insight, and most importantly it can even set the stage for changes that affect all of society in profound ways.

One of the best guests I hosted on my Doing the Opposite podcast was Mandy Hickson, England’s first ever woman fast jet fighter pilot, fighting on the front lines. Mandy fought in the skies over Iraq in a Typhoon class jet, flying into dangerous missions and ensuring the safety of British soldiers on the ground, and changed the structure of the RAF in ways that no one could have predicted.

Yet had it not been for a failure she experienced early on in her career, the impact that Mandy had on the RAF – and on the many women who have followed in her footsteps – may never have come about.

Despite being commended as an excellent pilot during her studies and her time in her University Air Squadron, Mandy found her progress blocked by a series of computer aptitude tests. After two unsuccessful attempts, she was blocked from taking the tests again – effectively ending her career path towards being a fighter pilot. The regulations were clear: two strikes and you’re out.

Mandy wasn’t willing to accept that her failure would be the end of her career. With the support of her mentor, she experienced the full range of benefits that are imparted by failure. She learned from her failure, reconsidering how best to approach the issue; she became motivated to change the rules, to bend the structure of the RAF to her will; she gleaned insight and understanding of the ways in which the system was flawed; and most importantly, she saw that there was a need for drastic change – a change that would ultimately lead to the alteration of the regulations and structure of the RAF itself.

Mandy was certain that the tests contained an unseen bias. She noted that 70% of women failed these tests, whilst 70% of men passed, a strange disparity given the aptitude of all the participants. After having written countless letters, chased down leaders and presumably called everyone in the RAF’s phonebook, Mandy wore down her superiors and they agreed to let her fly a Typhoon as a ‘test case’. Having proved herself as an exceptional pilot in combat, the RAF agreed to re-examine the tests and found that she had been correct. There was an unseen bias favouring men.

The tests were swiftly altered and a new cohort of women fighter pilots were able to pursue their dreams and follow in the footsteps of Mandy. A path that would never have been open to them, had it not been for her initial failure and her tenacious refusal to accept it.


So, what can businesses and leaders learn from Mandy’s story?

Firstly, failure isn’t the end. In fact more often than not, failure is the beginning of something new. It can allow you to shed your former limitations and exceed them in your second attempt. Businesses should obviously not court failure intentionally, but when finding themselves in a situation where failure is a guaranteed outcome, should seek to apply the mantras below.

  • Failure can be a source of experience and learning. There’s no shame in failing, but there is in failing to learn your lesson from the first time. Understand where you went wrong and make sure you won’t make the same mistake twice.
  • Failure can be a source of motivation. Nothing is more aggrieving than failure, but it can also provide the determination and grit to improve yourself and your processes.
  • Failure can be a source of insight. Sometimes it takes failing to spot a problem that otherwise may have remained unnoticed, to find an innovative solution.
  • Failure can be a source of positive development ,not just for you, but for those around you. Sometimes failure allows for changes that can have far ranging implications which can bring benefits in ways that could not be predicted beforehand. One person’s failures can open the door to successes for entire groups, teams and businesses.

Failure isn’t always positive. Often it can be unpleasant, even traumatic, but it also allows for change, growth and sometimes leads to successes that eclipse the scale of the initial failure.

So if you’ve tried and failed, take a step back and look at where you’ve gone wrong. You might just find that you’re one step closer to success.

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