Failure is Necessary for Achievement and Growth — Why Success is Dangerous for Learning

You can only succeed if you are willing to fail. You can only learn if you are willing to be terrible first.

Welcome to the Scarlet Ink newsletter. I'm Dave Anderson, an ex-Amazon Tech Director and GM. Each week I write a newsletter article on tech industry careers, and specific leadership advice.

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My Dad learned how to water ski when he was very young. He tells us stories of how his older brother would take him out at full speed, and would whip back and forth trying to knock him down. Because that’s what brothers do.

Every year for the past 60+ years, he’s made water-skiing a part of his summer vacations. He taught dozens of family members and friends of the family how to ski over those summers. One of his favorite sayings we’ve heard hundreds of times is “be the potato.” That’s not relevant to this article, but I thought I’d share.

Another thing he has repeatedly said was, “If you don’t fall, you’re not trying.” This wasn’t only skiing advice.

He has personally taken this to the limits. Considering how many times he went to the hospital over the years (trick water-skiing, biking, etc) due to his bias towards trying until he falls, my sisters and I rephrased it to, “If you don’t bleed, you’re not trying.” He’s also broken 3 bicycle helmets (and not his skull), which is a great argument for wearing a helmet, kids. Oh, and he even found a way to break his arm while swimming laps in a pool. Imagine. It boggles the mind.

My dad did not become an expert water skier by being a naturally gifted person. Or by reading a book about it. Or getting killer advice. He got there by falling over and over again.

I think at a high level, we all understand this. To get better at things, you need to fail a lot. But that’s relatively easy to understand if you’re talking about snowboarding or playing guitar. I hope most of you understand that you can’t start off good — you need to push your limits.

However, this fact is less obvious when we’re talking about work.

Why work success is dangerous for your continued growth and learning.

When we graduate from college (well, that’s the path for most of us) and start our professional careers, our days are filled with mistakes and learning. If we started off our career with a bit too much of an ego, we’re swiftly corrected when we realize that we’re incompetent.

“Can you explain that? I’m new here” is a statement you’ll make repeatedly in your first job. Those first weeks and months actively stretch our ability to perform, and we drastically improve our productivity as we enter each situation with an open mind. Our mind is open because it’s so empty. Those with personality issues that make them stay overconfident despite evidence that they have a lot to learn rarely keep their jobs long.

Then we have a success or two. Someone compliments us on hitting an important project date, a well-organized presentation, or a particularly insightful bit of code. Success feels great. We know what it feels like to be struggling, and holy smokes, success is much better. We love the confidence it gives us when we can relax because we know we have our work under control. When we have success at work, it makes work more pleasant, gives potential career growth, and security in our position. It can also be self-defeating.

So why is it bad? Well, imagine that junior engineer finally starts being comfortable with their tasks. They confidently grab similar tasks, and complete them as well. They understand this system, and these types of tasks. They’re reliable when completing these tasks, so their management team thanks them, and recognizes them as a success. Unfortunately, what can happen next is that they don’t pick up harder tasks. They don’t choose problems which will require new technology. They don’t try new ways of doing things because that might add risk to their ability to be successful. In musician terms, they want to keep playing the same song forever.

In interviews, we always give time for questions at the end. It’s a common way to wrap up interviews, and it gives employees time to get their own information about their potential new team.

I’ve repeatedly had experienced engineers ask, “Which coding language will I be using?”

This is a fine question in general, if they’re curious about what technology Amazon and their team are using. But a few times, I’ve also had it followed up with something like this.

“I only know how to code in Java, so I want to make certain I’m going to be using Java in this job.” or “Oh, C? I don’t know C, I only know Python. Is there a different team I could join which uses Python?”

I’ve had a similar question from a program manager a couple of times.

“Well, I’ve only used Kanban for project management. Is there a team using Kanban I could join?”

When you have been seduced by success, it can be tempting to want only success from now on. That ties an anchor around your neck. Unless your job allows you to mechanically execute the same thing for the remainder of your career (which sounds like a fairly boring career), growth and failure is required to succeed and thrive.