Build a list of fails you can be proud of

So there we were, shivering, wet, miserable and in the middle of nowhere. As the rain grew stronger the sky got darker, it became clear the camping trip we have been looking forward to all summer was not only dead on arrival, but replaced by a two-day suck fest that we were going to have to grin and bare. Today, I love camping in the rain. So what changed? I failed forward. In this post, we're covering how failure leads to growth.

Transforming ourselves into who we admire often requires us to develop mastery over some kind of skill or behavior. Counterintuitively however, the path to mastery is less about perfection and much more about repetition.

You see, you have to start with something in order to improve it. Put another way, you have to have a baseline of performance before you can refine it. Quality and mastery come through a continuous stream of tiny refinements that stack and compound on each other over time.

When Covid hit, my wife and I made a concerted effort to learn how to camp, since it was one of the few activities we could do safely. Friends of ours had taken us camping a few times over the prior years, and we always had had fun.

We were both total newbies though, and we had to learn a lot from scratch. We bought the absolute basics in terms of gear: a tent, some chairs, and a camping stove, and booked a bunch of trips.

Looking back, those first few outings were tragic. One time, I forgot to pack utensils, so we had to eat with our hands at every meal. Another time I completely forgot to bring firewood, and we had to build our tent in the dark.

Idea 1: You have to pay the toll

Each trip we took seemed to bring a small lesson to learn, and each of those lessons went into the preparation for the following trip. By the time we had gone on five or so trips, I'd say we had graduated from total newbs to somewhat competent campers, and this highlights an important idea:

Any time you decide to develop skills in a new area, you should anticipate that there will be a certain amount of failure that acts as a toll to pay on the path toward mastery.

Adding utensils and firewood to my camping checklist are each examples of how mistakes contributed to the development of my camping intuition.

These mistakes were also finite. I only had to learn each of those lessons once to improve. While not every lesson can be learned the first time life teaches it to us, it's still true that there's a fixed number of times we'll need to fail before the lesson finally sticks.

Seeing and expecting failure reframes the journey. Even though the amount of fail is unknown, it's limited. There's a set number of mistakes you'll need to make before you get good, and the sooner you make them the better.

Idea 2: Learning is proportional to Struggle

Whether you're learning a new language, developing a work-related skill, or exploring a new facet of a hobby, I highly encourage that you not only anticipate some failure, but even go so far as to seek it out.

Now, I know that can sound a little strange, actively looking for ways to fail in all, but this points us to our next key idea: That learning is proportional to struggle

Back to the story at the top of the post. Despite having completed several successful camping trips, and feeling pretty good about my camping abilities, being totally miserable in that downpour gave me a humbling reminder that I had never learned how to work with tarps for rain protection. Until then, I had only ever camped on clear, sunny days.

Unlike forgetting cutlery or having to set up a tent in the dark, being unprepared for rain wasn't a minor inconvenience, it was a total fail that resulted in a lot of struggle and frustration over a two-day period. That trip left an impression, and it motivated me to level up my capabilities in a big way.

Coming out of that experience, I resolved to learn how to camp in the rain. The weather in the South East can be unpredictable, and I knew that it was only a matter of time until we encountered rain again.

I dove deep into bush-crafting YouTube, teaching myself how to tie basic survival knots and how to make emergency shelters. While I was at it, I also learned how to make a fire in the rain, which didn’t even know was possible. I bought tarps and cordage, and spent several afternoons practicing my skills in the backyard.

Months later, we found ourselves getting caught out in rain again, but this time, the experience was wonderful. We were perfectly comfy sitting around the fire as we listened to the rhythm of the rain bouncing off the tarps overhead. Taking in the uniquely fresh air that only comes from wet earth, I was filled with a tremendous sense of accomplishment. I had worked hard to earn that moment.

In summary

The three ideas we covered here are all connected. When you set out on the path to mastery in a given area, lean into the fact that repetition and not perfection, is how you'll establish a baseline that can then be refined. As you put in the reps, expect that there's a fixed amount of fail you're going to have to experience before you improve, and then finally, embrace the big fails when they come since that's where the fastest and deepest learning happens.

Do you have a story to share about mastery and failure? If so, I'd love to hear about it! Please leave a comment letting me know what you were working towards, and if any of the ideas covered here came into play.

Learning into your fails gives you a massive leg up in developing mastery, but how do know when failure begins to compromise consistency? Be sure to check out this post here to find out.

In case you’d like to see a spoken version of this essay, be sure to check out this post on YouTube.