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The Internet is inundated with advice about how we should learn from our mistakes, and how our failures are our biggest teachers. Yet when push comes to shove, we cannot manage to really wholeheartedly embrace that.

And we’d like to tell you that’s okay. 

It’s human to err, but even more so to dislike screwing up. After all, for those things that matter, we put in effort to ensure that we do the best job we possibly can. 

Yet sometimes this may not be enough, or sometimes we simply get it wrong. 

While you shouldn’t beat yourself up about not feeling great about your failures and loving the experience of making mistakes, it is something we can all work on, a little bit at a time. 

In many people we coach, there’s this intense shame that accompanies mistakes. It is more pronounced in those who struggle with self-esteem issues. 

In politically toxic organisations, this can further devolve into blame-games and throwing others under the bus.

The challenge is, that it’s not like people set out to do a bad job. But all of us, at some time or another, do poorly, or make errors. 

Why are mistakes taboo? And why do we beat ourselves up about them?

It could be that when we are socialised, we haven’t been prepared for failure – and failure is inevitable.

Nobody fails in fairy-tales except the villains. People are 100% good or just completely bad. If they are bad, they lack any redeemable qualities. They are unforgiving towards transgression.

We have few role models we watch fall and pick themselves up again. We either see them after they’re super successful at which point a claim of past failures doesn’t do the trick.

Or we just see success.

This black and white picture of the world is harmful as it is rarely the way it happens. And in those with low self-confidence, an inability to make mistakes can cost growth and success – because it costs people the inability to take risks. 

Social media, with the trappings of self-presentation, only compounds the problem. 

So, what can we do as leaders, or individuals to make mistakes less uncomfortable?

In Radical Candor, Kim Scott cites an example of a 1990s startup using two stuffed animals to encourage open praise and criticism. People nominated their colleagues for the “killer whale” award – for exceptional performance.

But much more interesting is the “Whoops the Monkey” which was a self-nominated award, for anyone to speak about a time they had screwed up. 

When Scott introduced this at her company Juice and later at Google, she had to add a financial incentive to it, in order to make people volunteer. But once they got going, they were able to switch from shame to growth –  an important factor for future success. 

In No Rules Rules Reed Hastings and Erin Meyer speak about the Netflix practice of encouraging people to sunshine their mistakes. 

While not all of us can emulate all parts of what these Silicon Valley tech giants do, this simple concept of speaking about mistakes and getting our people more comfortable with them, can do wonders for their willingness to address them more effectively, as well as avoid trying to cover up or making similar mistakes in the future. 

Eventually it leads to building a culture that allows for lots of learning. A side benefit is the elimination of the huge amount of emotional energy wastes when you are feeling ashamed of something you’ve done. 

A crucial part of this is how we, as managers, handle the mistakes made by our team. While they need to understand their errors, berating people or making them feel stupid is not productive.

Neither is sugar-coating the situation and telling them it’ll be alright, if in fact it won’t be.

You need to encourage a comfortable honesty around mistakes and failures, that allows learning – not just for the individual, but the whole team. 

And if you’re a person that struggles with coming to terms with your mistakes, find ways to build a new picture. Remember that mistakes and failure are uncomfortable – so don’t worry if you can’t see the bigger picture right away.

But if you let it get the better of you, rather than being able to process it in a healthy way, you lose the benefit you stand to gain.

A winner isn’t someone that hasn’t screwed up. She or he is someone who has not let their failures stop them from going where they want. 

Sure, that picture may change, and failures may make you realize you need to reshape what it is you want – but so long as you are driving it and being true to yourself in the process, you are winning.

In the words of Paul J Meyer, “Mistakes are merely steps up the ladder.”


  1. Great stuff. Yes, mistakes are our greatest teacher.

    1. Thank you for reading! We are glad you liked it!

  2. I have screwed up so many times, but then what is life without screwing things up haha! Great blog!

    1. And your growth must have been that much more invaluable! Thank you for reading 🙂

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