#177 How Badly Have You Failed?
#177 How Badly Have You Failed?

This may feel like an edgy question. For starters, failure obviously depends on how you define success. I co-founded a start-up over 20 years ago that, despite a solid business idea and incredible effort by the whole team, failed to get to market and died after 2 years. On any measure (both intent and outcome) it was a failure.

And yet, the lessons learnt in that failure were instrumental in bringing me to where I am right now, so I no longer think of failure as bad and success as good but rather in terms of learning. That isn’t the same as deluding ourselves that we didn’t fail. We did and we failed badly. The important thing for me was that we were ambitious, and we learned so many valuable lessons.

However, for a while this led me to become more risk averse and I remember being shocked when my own coach asked me:

Are you playing to win or not to lose?

It was one of those questions that stopped me in my tracks and made me realise that I was playing it safe and no longer putting myself in situations where I might fail badly.

I made a vow to myself to follow my heart and my gut wherever they lead regardless of the outcome and continue to do so. It also made me appreciate process (how it is done) more than outcomes (what is done). If I do everything I can on a daily basis to deliver the vision and still fail badly, that is fine in my book.

  • So, how badly have you failed?
  • If you haven’t failed badly – how ambitious do you feel you have been?

Questions in the Image:

  • How badly have I failed?
  • How ambitious have I been?
  • Where am I afraid to fail badly?
  • Am I playing to win or not to lose?

Want to Read More Around This Topic?

Playing to Win: How Strategy Really Works by Roger L. Martin and A.G. Lafley (link to Amazon.co.uk). This is an intriguing book that describes itself as “a playbook for winning”. Blurb aside, it likely will help you build a stronger strategic process and put the numbers more on your side.

Nurturing Curiosity – Daily Practice: This is part of the Nurturing Curiosity series of tools, insights and questions designed to help nurture curiosity as part of our daily practice. In point of fact, every interaction we have is an opportunity to question what we are observing and how we and others are seeing the world. Also remember that questions come in many forms throughout our day – a discussion with colleagues around accountability raised the question of “If I am accountable to myself, to whom am I accountable to?” I have a voice of perfectionism in my head. He isn’t as loud as he used to be but he is still there. I certainly don’t want to be accountable to him and he isn’t always reasonable. To whom then might I be accountable?

About Tom O’Leary

I coach, mentor and teach high performers to thrive by focusing on the choices we make.

In truth, our paths in life are paved by those choices. We can talk all day but to make our lot better we need to make the smartest decisions and then execute on them as best possible.

My view is that it is about slowing down to speed up. This means spending time being curious and contemplating what might be possible so that when we take action, we can bring all our energy and power to bear.

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