Playing the fool

Andy Ryan
3 min readMar 22, 2022

Should we play the fool? and Should we encourage others to play the fool?

I’m not talking about stupidity here, I’m referring more to the notion of the medieval court jester. A character who is has the courage to empty himself, start anew and try things in the service of others.

I grew up in an environment that was at times hard and strict but at other times playful, encouraging and foolish. My dad played the fool and I followed his lead. It’s how I learned to be a “learner.” My dad was also an engineer, and it would have been very natural for him to guide in a very pragmatic and precise way. When he brought home that first computer and allowed me to start working with it, he could have easily demanded that I learn it the same way he learned it and I work with it in a very specific way, HIS. He gently showed me a few things and encouraged me to find my own way. I wrote the proverbial “Hello World” program, and I encountered an error. I was surprised by my dad’s reaction. He actually got really excited and encouraged me to continue and figure it out. He was basically giving me permission to fail.

Now, imagine if he didn’t give me this permission and when he saw my mistake he said something like “Andy, that’s not the way you do it! You need to do it like this!”

What do you think my life would have been like? I doubt I would have embraced technology as much as I have, I may not have learned anything about computers and my career would have been completely different. This seems a bit extreme, but certainly plausible.

Think about the times in your life when you refused to learn because someone, whether your parents, friends, society didn’t allow you to be free and foolish in your learning process. How many times did I not try something because I was afraid of being thought of as silly? How many times have I censored myself?

A number of years ago we decided to go away for Thanksgiving to a beautiful, old grand hotel. There were lots of activities planned for the long weekend including a waltz. Those who know me, know I don’t dance, it’s something I talk about. In fact, I’ve said to my wife on a number of occasions, “boy I wish I could dance like so and so.” On this particular occasion, I got it stuck in my head that I REALLY wanted to try this Waltz thing and I REALLY wanted to dance with my daughter. At the time, my daughter was in her early teens. I had some anxiety over appearing foolish, but I can’t imagine how much anxiety a teenage girl might have. She reluctantly agreed and we stepped out onto the floor and danced. We both agreed to play the fool together and we learned. We learned because we gave each other permission to be free and foolish.

How can we learn if we don’t play the fool?

Some of my favorite memories as a Sales Engineering leader were the moments when I had the opportunity to give my team permission to be free and foolish, allowing them to learn. One time in recent memory, I brought the team together for an offsite. It was the first time many of the team were actually meeting face to face. I could have created an event that was focused on the sales numbers and goals for the upcoming year, individual tasks that needed to be accomplished, etc. Instead, I saw this as an opportunity for learning. I structured the days around a few learning goals, provided some supporting material, but then encouraged them to figure things out. Of course I was there to support, and when one person or a group of people made mistakes, I made sure to praise the work and the journey so far and encourage them to continue. Just like my dad did.

To all my fellow Sales Engineers out there, empty yourself, be foolish and free. Never stop learning.

To all the leaders out there, give your people permission to be foolish and free. Encourage them to continue learning!

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