CHAPTER 13

Give Yourself Permission to Make Mistakes

A few years ago, I was scheduled to fly to Dublin, Ireland, for a speaking engagement, and when I got to the airport I realized I’d forgotten my passport at home. I felt mortified and embarrassed—and then angry when I found out I wouldn’t be able to get on my flight. After a few hours of stress and drama, I was able to get myself on another flight, which got me to Ireland in time for my event but cost me quite a bit of money and forced Michelle to have to drop what she was doing and rush to the airport with my passport.

As I was waiting for Michelle to arrive, my heart was racing and my mind was flooded with self-criticism. The conversation that my gremlin was having with me in my head went something like this: You idiot! How could you be so stupid? Your passport was sitting right on your desk where it always is, and you just forgot it, for no reason. You’re a flake! You get upset with Michelle when she forgets to itemize a receipt from Costco and here you make this ridiculous mistake which has now cost you $1,300 and caused unnecessary stress for her, the girls, and for you! You should be ashamed of yourself!

No matter what I tried, I couldn’t stop listening to my gremlin saying these horrible things to me. By the time Michelle arrived at the airport, I was so upset with myself, when I came out to grab the passport from her at the curb, I cried in her arms. She was so kind, loving, and understanding in the midst of my anxiety, self-criticism, and embarrassment, I felt loved and supported by her in a beautiful way.

Even with the drama of the situation, I did realize that in the scheme of things, forgetting my passport wasn’t a huge deal. However, it really upset me and caused me to reflect on how I react to mistakes—mine and other people’s. What I realized is that I don’t give myself or those close to me much permission to make mistakes. While mistakes aren’t a huge issue in my life, I actually spend and waste a lot of time worrying about making them, and also find myself being unnecessarily critical of those around me when they make mistakes (both overtly and covertly).

Michelle’s kind response to my mistake and the negative impact it had on her was a great model for how I want to be when someone around me makes a mistake—helpful, loving, and accepting. It also reminded me that having empathy and compassion for myself when I make a mistake is a much healthier and more positive way to deal with it. Sadly, my stress and self-criticism in response to the whole passport debacle took a toll on me—I didn’t sleep much on my flights over to Ireland, and by the time I arrived, I was actually physically sick. It was a painful way to learn a very important lesson.

How do you relate to yourself and others when mistakes are made? While it often depends on the nature of the mistake (some are bigger than others, of course), many of us tend to be hypercritical with ourselves and those around us when it comes to errors. And the stress we associate with mistakes can actually make a difficult situation even worse.

Our fear, resistance, and self-judgment when it comes to making mistakes can also keep us from learning and experiencing new things. Children are great reminders of this. My girls have taught me so much in this regard. Over the past few years, watching my girls learn how to ride their bikes, swim, and ski has been a wonderful and inspiring experience. While these activities are fairly simple, they aren’t all that easy to learn, especially at first, and they involve a lot of mistakes and failure in the process.

I didn’t learn how to ski until I was 13, and although I enjoy it, it’s not something I’ve ever been all that good at, which also means that it hasn’t been a priority in my life. Michelle learned when she was five and used to go up to Lake Tahoe to ski a lot as a kid and as a teen. We went there for our very first ski trip together as a family in April of 2012. Samantha had just turned six and Rosie was three and a half. The plan was for Michelle and me to ski together, amazingly for the first time in our 11-year relationship at that point, and we were going to put the girls in ski school to see if they liked it. Michelle and I ended up having lots of fun, and the girls were troupers in ski school; neither of them absolutely loved it, but both of them were willing to try.

We decided to head back up to Tahoe the following January. This second trip went even better and the girls were starting to enjoy ski school—although the learning curve was still pretty steep and there was lots of falling down, failure, and mistakes involved for both of them. Samantha, now being almost seven, was picking it up a bit faster than her four-year-old sister, but they were both making progress. On the final day of our third ski trip, we took the girls out of ski school at the end of the day, and decided to see if we could ski down the mountain together. I think Michelle and I were more nervous about it than the girls were. We all got on the ski lift, which is one of the scariest parts of the whole thing, especially with young kids. Thankfully, the girls were fine and totally excited—in fact, they were giving us pointers about safe ways to get on and off the lift.

At the top of the hill, we got off the lift, adjusted all of our gear, and took a photo. It was a beautiful day at Squaw Valley in Lake Tahoe. And as soon as we were set, we started to make our way down the mountain as a family. It was amazing and exhilarating, but a little nerve-wracking as well. Incredibly, we made it all the way down, even little Rosie, and although there were some falls and stops along the way, there were no major issues and it was lots of fun!

As simple of an experience as this was, it blew me away. I felt inspired and proud of my girls, not so much for their skill as skiers but for their willingness to learn something new and potentially scary, and most specifically their willingness to make mistakes and fail, and still do it anyway.

What if we had more freedom to make mistakes and gave the people around us permission to mess things up as well? It’s not that we’d start rooting for or expecting things to go wrong; we’d simply have more compassion and understanding when they did (which at some level is inevitable in life, family, relationships, and business).

By giving ourselves and others permission to make mistakes, we actually create an environment within our own being and within our key relationships and groups that is conducive to trust, connection, risk-taking, forgiveness, creativity, and genuine success.

While it can seem a little risky, and even counterintuitive, allowing more freedom for mistakes to be made creates the conditions for fewer errors to occur, and more fun, courage, and productivity to take place.