My Dad learned how to water ski when he was very young. Every year for the past 60+ years, he’s made water skiing a part of his summer vacations. He has taught many family members and friends how to ski. One of his favorite sayings we heard repeatedly as we were growing up was “If you don’t fall, you’re not trying.” Considering how many times he went to the hospital due to his deep passion to get better at things, my sisters and I rephrased it as “If you don’t bleed, you’re not trying.

My dad, after thousands of falls.

I think we’ve all heard that you learn more from your mistakes than your successes. A piano player repeatedly playing a perfect “Happy Birthday” will never suddenly have the ability to play Chopin flawlessly. Our ability to do hard things only comes from failure. To play Chopin flawlessly, you must first play it terribly and learn from your mistakes.

That which does not kill us, makes us stronger — Nietzsche

Success is dangerous to learning

The early days of our professional careers are filled with mistakes and learning. “Can you explain that? I’m new here” is a pretty easy statement to make when you were hired 3 weeks ago. Those first weeks and months stretch our ability to perform, and we drastically improve our productivity as we enter each situation with an open mind.

Then we have a success or two. Someone compliments us on a presentation, or a particularly insightful bit of code. Success is awesome. It feels great. We love the confidence it gives us when we hit something out of the park. When we have success at work, it gives personal satisfaction. It gives potential career growth. It gives us security in our position. It also can be self-defeating.

I’ve seen this pattern a number of times. An employee gets comfortable with their current tasks. They confidently resolve similar tasks at a consistent rate over time. They know how to do these types of tasks. They are reliable at those tasks. However, they don’t pick up harder tasks. They don’t pick up new technology. They don’t try new ways of doing things. They want to play the exact same song, forever.

In interviews, I always give time for questions at the end. I’ve regularly had experienced engineers ask “Which coding language will I be using?” This might be related to their curiosity about which technology their area of Amazon is using. I’ve also had it asked with the added context of “I only know how to code in Java, so I want to make certain I’m going to be using Java in this job.

When you have been seduced by success into wanting only success from now on, you’ve tied an anchor around your own neck. Unless your job allows you to mechanically execute the exact same thing for the remainder of your career, growth and failure is required to succeed and thrive.

Fear kills growth

Making mistakes at work can be scary. It makes you feel vulnerable when you’d prefer to feel secure and confident. You have your pride to protect, and your social status to worry about.

  • Kindergartners have no problem asking a stupid question with their whole class watching. They are interested in learning, and haven’t started protecting their social standing.
  • Middle school students are notorious for being afraid to ask the wrong question, or look ignorant in front of their classmates. They are often focused on improving their social standing, less on their own personal growth. Kids can be silly like that.
  • In college, many of us grew out of our fear of looking stupid, because we had things we needed to learn. It was appropriate to ask questions when needed, because we were all there for the same purpose.

I’ve seen far too many professionals act as if their social standing is more important than learning. They act like middle school kids rather than serious students. They nod in agreement with decisions they don’t understand. They work to complete tasks without understanding the “Why” behind them. They dodge high visibility tasks in fear of how they might be perceived. They sit quietly when their management chain makes a decision they know is wrong. Their fear makes them short sighted, neutering their growth in favor of an imagined short term gain, or fear of loss.

Perfection / short term gain vs leadership / growth

A leader is not someone who leads due to being flawless at their job. A leader is someone who is a role model for others in how they should act, and what they should value.

If you are focused on short term performance, you might look for excellent execution. If you want to make an awesome website design today, you would narrowly focus on hiring an employee with excellent current skills. Specific skills you would need for the task today.

If you want the best design company 5 years from now, you would focus on a different set of criteria. You’d want someone willing to experiment. You’d want someone who tries things they’re uncomfortable with. You’d want someone excited about learning. You’d want someone willing to push the boundaries to ensure you don’t get left behind.

At Amazon, our leadership principles are steeped with nuance regarding long term value vs short term gain. We value ownership because employees care about paychecks but owners care about long term success. We value learning and being curious, because the ways you solve problems today are not the ways you’ll solve problems tomorrow. We value having backbone and sticking your neck out, because absolutely no one has all the right answers.

Confidence, bravery, and failure

I am not perfect at my job. There are aspects I feel I do better than average, and aspects where I do worse than average. Impostor syndrome is a well known phenomenon because we all can so easily see our own flaws.

It’s great to recognize your own flaws, as it helps us improve. However, the requirement of a strong leader is to move forward with confidence and bravery, despite your flaws. This doesn’t mean hiding them. This doesn’t mean masking your mistakes, or avoiding failure. It means being a role model for your management, peers, and team members. Not just for the things you do well, but for your willingness to do things not well.

The emotional challenge is that confidence often comes from success, and failing can hurt your confidence. It takes bravery and a willingness to be wrong to move forward despite your inevitable failures.

On various occasions, leadership groups I’ve participated in have asked for someone to give a talk on a topic. Perhaps to a university group regarding recruiting, or perhaps to an internal group of employees on a topic. I’ve always made a point of volunteering. I’m an introvert. I don’t enjoy public speaking. My heart rate doubles standing in front of a crowd. Still, I am willing to force myself through an uncomfortable situation and potential public failure to ensure that I will be better at this important skill 5 years from now. I’ve had talks which went well, and ones where I stumbled and rambled and lost my train of thought. I learned a lot through each event, particularly those where I performed poorly.

One of my favorite employees of all time was a manager who worked for me a few years ago. He had great functional skills, but that’s not why he was one of my favorite employees. In a room full of my management team and senior engineers, I could always count on him to be a voice disagreeing with my decisions. He was one of the more junior people in the room, but he was focused on doing the right thing. It is common to have well performing employees. It is much less common to have brave employees willing to stick their necks out and fail. He wasn’t always correct with his disagreements, but he felt it was more important to try than to be right.

Next steps

This skill is critical to long term career success. Being willing to fail. Being willing to be embarrassed. Being willing to sacrifice current social status for long term gain.

A few suggestions I’ve used in the past, depending on the employee, their role, and their own hesitations:

  1. You should purposefully force yourself in a certain leadership meeting to disagree at least once with one of the senior leaders. I said it was inevitable they’d hear something they disagreed with, and they should build public disagreement muscles.
  2. You should explain to Y employee that they’re not performing and their job is at risk. This new manager was terrified about giving feedback poorly. They were terrified about the social confrontation, and how they other employee might feel. I walked them through the necessary steps for the talk. The best gift you can give an under-performer is honesty and feedback. I insisted that this manager take a deep breath and go through the emotional pain to get to the long term benefit for both of them.
  3. You should write the XYZ strategy document for our team. I said I understood they were terrified about their English and writing skills, but also knew about their career ambitions. I said I’d be willing to help them with their writing, and they needed to be willing to present a less than perfect document in front of others. They would quite likely need to deal with painful feedback and constructive criticism. Only through this failure and feedback cycle would they be able to gain this critical skill.

In general, growth is personal to everyone. A great way to find your best areas for growth is to look for those things you fear. You fear you’ll screw something up. You fear you’ll embarrass yourself. You fear that you’ll reveal that you’re not quite as skilled as the person you’re pretending to be.

Now build trusting relationships with co-workers and your managers. Find enough emotional and career safety so that you can fail and grow. Figure out a way to avoid complete disaster, but still go through the growing pains which are necessary for self-improvement.