Skip to content
Ray Gesualdo
A beautiful desert landscape.

Abandon the Fear of Failure

November 16, 2022 | 6 Minute Read | Category: Learning

Well, it was bound to happen sooner or later. Over the summer, I took down production. I didn’t want to. I didn’t mean to. But it happened anyway. As the adrenaline rush of diagnosing and fixing the problem slowly wore off, I did as any responsible member of society does and tweeted about my experience.

Tweet reading "Hi, I'm a staff-level engineer and I just took down prod with a duplicated file extension 🤦‍♂️🤦‍♂️🤦‍♂️"

Turns out, this resonated with a lot of people. As of this writing it has 2,848 likes (which is about 2,845 more than my tweets typically get 😂). The responses varied widely. Some questioned whether I still had my job (of course I do). Others had opinions about my competency or the processes we have in place to prevent such things from happening. But most simply commiserated. Turns out, making mistakes is a common human experience! And sometimes those mistakes take down prod. We’ll come back to that in a little bit.

A related personal story

I have two little ones. My son, the older child, just turned three years old. It’s a joy watching him learn and grow everyday, and to be a part of that process with him. Of particular interest to me has been watching him learn to speak. At first, this meant him picking up on random words my wife and I would say. We’d say something and he’d almost absentmindedly copy it. He didn’t copy it perfectly. In fact, his version was typically only one syllable. And he didn’t always get the sounds right either e.g. his “w” sound was an “h” sound.

As he’s gotten older, he’s picking up on more complex words. He’s refining his pronunciation. He’s stringing together longer complete thoughts. And I’ve noticed something quite profound about the way he learns: there is absolutely zero shame or embarrassment when he gets something wrong. In fact, he’s not trying to get it right all the time. He takes what he experiences - his parents making a sound or performing an action - and mimics it in a way that makes sense to him.

As his parent, I don’t correct him in any sort of punitive way. I may restate what he said so that it’s grammatically correct and he can hear what that sounds like. But I don’t tell him he’s wrong or make him feel bad for not saying something correctly. He’s learning. To expect Shakespearean prose from a child his age is ludicrous. Yet, how many times do we heap similarly ludicrous expectations on ourselves when we first start learning something?

At the office

One of my favorite sayings at Salesloft is we should “learn faster than the rate of our own experience.” Making mistakes - failure - is one of the greatest teachers. Most of the time though, mistakes and the lessons we learn from them are never shared or socialized. Which is a shame because in doing so we can all actually grow faster together.

In the “pre-Covid” times at Salesloft, we had a Cube of Whoops™, an actual physical metal cube one could hold. The Cube of Whoops was not bestowed. It was voluntarily taken. If you made a mistake, particularly if it had a significant impact on coworkers, customers, or the platform, you could take the cube from the current holder’s desk. The physical act of taking the cube from someone else’s desk was significant in that you were owning your mistake. It wasn’t a bad thing to take the cube, provided you had learned from the experience. It didn’t stop there though. When taking the Cube, you also had to email the entire engineering org noting the mistake you made, how you fixed it, and how to mitigate such things from happening in the future. While this whole process may sound scary, it actually wasn’t at all. Coworkers of all seniority and experience levels sent Cube of Whoops emails. It normalized admitting mistakes and transformed one person’s learnings into an entire org’s learnings. The emails almost always generated great discussion in the conversation threads that followed as well.

This is just one example of myriad ways we can learn faster than the rate of our own experience. But most importantly, in order to do so, we can’t be afraid of admitting our mistakes.

Self-defeating façades

The pressures we feel (external or self-imposed) to limit our embarrassment actually hinder us from learning and growing. We want to appear competent and intelligent so we shy away from situations or behaviors that communicate the opposite. We don’t know a specific piece of jargon someone used in a meeting, but we don’t ask about it because we’re not sure how that would reflect on us. We’re learning a new skill, but don’t want to look silly asking (what we feel are) simple questions.

We hold up these “competency façades” because we feel our expertise in one area of life should automatically translate over to another. It doesn’t and that’s okay. If anything, our lack of expertise in a new area is an opportunity to be genuinely curious, to explore something we haven’t before with a beginner’s mindset. Fear of embarrassment squelches this curiosity.

Thinking back to my son learning to talk, he was never self-conscious about his speech patterns. He felt free to try, mess up, try again, get closer, try it differently, make some mistakes, step away, and keep trying. And in doing so, his ability to talk has exploded over the past year and a half. I have a personal aspiration to learn to speak another language. But when I think about how I might do so, I know my first instinct won’t be to learn as my son did, being comfortable mispronouncing words or messing up grammar. I will be tempted to wait until I’m confident my skill level won’t embarrass me or make me look foolish. That won’t help me grow.

Take chances, get messy, make mistakes

Yes, I just quoted Ms. Frizzle from The Magic School Bus. Her admonition holds as true today as it did in the mid-90s. Taking chances, getting messy, and making mistakes are all a part of the learning process. They allow us to stay curious. In life, to learn and grow, we have to acknowledge our fear of failure or embarrassment and step out anyway. That’s partly why I tweeted about my mistake. No shame in making a mistake and learning from it. And if we can help others learn from our experiences by sharing them, then all the better.

Go to top