My wife, Jasmine, shared this wonderful article with me a few weeks ago. The author describes her first experience with strength training, coming from a distance running background. She explains what I believe many of us would agree with: It’s easy to like doing things we know we won’t fail at.


“I found it easy to largely avoid failure in my workouts: When I went for a long run, I know I would complete the distance, even if I did so slower than I planned to.”


A question for you to think about as you read this: As you’ve gotten older, how often do you enjoy learning new skills? Learning a new language, learning to code, learning how to work out properly, the list goes on. I’m going to guess the answer is “not all that much.” Me too. It’s hard! Writing this newsletter is something new, and it takes a lot more work for me to write this than to pick 350 pounds up off the ground.


Why should we do it then? Because “the CEO doesn’t do what feels good all the time.” It’s natural for us to want to do what we’re good at it. It feels good doing it. But learning a new skill involves a ton of try, fail, try, fail, try, fail. And dammit, we don’t like failure!


Why the hell not? Failure is what teaches us; failure is how we grow; failure is how we earn what Arthur Brooks calls satisfaction, a key macronutrient of happiness.


Yet, as the author of this article points out, we are raised to fear failure. If we fail as kids that means something is wrong with us. So, we avoid doing those things. You’re terrible at math, ok, no more math. You’re terrible at writing, ok, no more writing. It’s infuriating to think of how damaged we are as we become adults and leave the sheltered world that is our education system.


This is why I love what I do. Many of you hate working out. It hurts, we’re sore afterward, and it takes a lot of energy. Moreover, I will often ask you to do things that are much more challenging than you would do on your own. I do this because, in the short term, I want you to fail. I want you to push yourself to your limit. This doesn’t mean you should leave a workout feeling exhausted and defeated. Quite the contrary. You should end every workout feeling exhilarated and a tremendous sense of accomplishment. That you did something truly difficult, maybe even enjoyed it a little, and you know you are building towards something off in the distance.


When we do these things, we find our point of failure, our limit is ever-expanding. We are expanding our foundation — similar to how expanding your heart rate zone 2 range expands the foundation of your aerobic health or how reading expands your foundation of words from which you can pull from.


“Almost a decade after my first failed attempt, and now at 40 years old, I walked up to the judges at a competition and stared down at the 55-pound dumbbell resting on my feet. The first time I tried to press it, my nerves took over. I missed the rep. For my second attempt, I shook off the frustration, planted my feet in a better position, hoisted the dumbbell to my shoulder and — finally! — nailed it.”


If there is one thing I hope you take away from this piece, it’s that the next time you try to do something positive for yourself that you know will be difficult, you approach it with a smile on your face and say, “Hello failure my old friend.” And yes, I am talking to myself as much as I am talking to you.


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