Make Room For Being Wrong

One of my coaching clients is a CMO of a fast-growing startup. He hosts “The Monthly Mess Up Awards” for his team each month. Each team must have at least one representative share the biggest mess up they made in the past month. The framework for how they share is an important part of the proceedings:

  • What were you trying to accomplish?
  • What did you think was going to make this new idea different? 
  • When did you notice things weren’t going right?
  • What tipped it over the edge and made you stop?
  • What did you learn?

It has become a must-see event for the team and has created a culture of experimentation and risk-taking as they continue to chase down their methodology for growth and success across the department. It has also produced incredible results after multiple failures, multiple Monthly Mess Up award submissions, and multiple opportunities for others to weigh in on how it might be done better the next time. 

Perfection is the opposite of curiosity. 

Perfection leaves no room for failure or for learning through experimentation. 

Perfection makes someone right and everyone else wrong. 

Curiosity leaves room for massive failures because the learning from the outcomes are more important than this most recent attempt. 

Curiosity leaves room for collaboration and incremental growth until exponential growth is found. 

Last year I made a huge investment. Not huge in the grand scheme of things, but one of the bigger investments I’ve personally ever made. I know exactly why I did it. I know exactly why I believed it would work. But I also know now that it will not play out the way I had hoped. With hindsight as my instructor, I know exactly where that investment went sideways and why it will likely not recover. 

But that is what taking risks are all about. 

In this newsletter community, I took a risk and built out a paid tier. But as of February, that tier will be removed, at least for now. I couldn’t bring enough value to those incredible people who believed in my vision for a private curious community. (If you’re a Roomie - be on the lookout for another email explaining what comes next.)

We all need to fail more. 

And I hope that me sharing some of my recent failures will inspire you to do the same. There are lessons in every attempt and your courage will grow as your understanding of the problem and the other ways to create a solution grow. 

If you don’t know the last time you failed, it’s time to go do something where the outcome isn’t certain. It’s time to not accept perfection as a reason to play small. 

Send me your best fails and what they taught you - I’ll feature the best ones in next week’s newsletter (with your permission.)


Quote That Rings Increasingly True

"We don’t teach people how to get back up when they fall. Because we don’t teach people how to rise, most never take the leap." - Brené Brown

Quote That I Can't Unhear

We live in a world with a lot of insecure, jealous people. Some of them are our best friends. They are blood relatives. Failure terrifies them. So does our success. Because when we transcend what we once thought possible, push our limits, and become more, our light reflects off all the walls they’ve built up around them. Your light enables them to see the contours of their own prison, their own self-limitations. But if they are truly the great people you always believed them to be, their jealousy will evolve, and soon, their imagination might hop its fence, and it will be their turn to change for the better.
- David Goggins, Can't Hurt Me: Master Your Mind and Defy the Odds

Quote Worth Really Considering

"One of the great balancing acts in life is to be cautious and daring at the same time. Cautious enough to avoid stupid mistakes, prevent burnout, and maintain a margin of safety.Daring enough to bet on yourself, to do the things you would regret leaving undone and to be willing to be uncomfortable in the short term so you can learn and grow in the long term." - James Clear