Mistakes are how you learn. If you're not making mistakes, you're not growing.

I think many of us have the mistaken assumption that as we advance in our careers, we should make mistakes less often. We will grow in experience, and the wisdom we've gained will lead us to a place of consistency and success.

I'm not saying that you shouldn't get better. If you start your career in software development, writing a simple script, I would hope that you can do that better as time goes on.

You will get better at what you're doing, but continuing to do the same thing will lock you in place. Unless you're done with your career and ready to retire, stopping all personal growth feels disappointing.

If you're comfortable in your job, it might mean that you're no longer growing.

If you're proud of how well you execute, it might mean that you're executing on something too easy.

Over time, I can think about my most important lessons, and they're always connected to a painful mistake. I thought I'd share a few mistakes, and what I learned along the way. If you find the below interesting and think more articles like this would be interesting, reply to the newsletter and let me know!

The time when I let an employee screw up something significant.

At Amazon, we were heading towards Q4 peak. Part of our organization's process was that each service owner (area of technology) would present their readiness for peak to other senior leaders. This theoretically should include how they tested their ability to scale, risks, traffic expectations, and anything else relevant.

I had multiple managers reporting to me. I offered to my managers that I was available to review their readiness presentation with me, before their presentation to leadership. All of my managers except for one reviewed their presentations, and I gave them significant amounts of feedback. One manager didn't schedule anything with me.

I could have made it required. I could have told him this was a bad idea. I shrugged, and thought, “This is a great learning opportunity for him.”

As I expected, his presentation wasn't sufficient. He was missing metrics, he didn't have answers to people's questions, and he ended up looking incompetent to senior leadership. He was asked to present again when he was prepared.

Through this process, I thought this was a fine situation. He could easily fix the presentation, and try again. I thought this was a good learning experience for him.

My manager pulled me aside, and explained why I had made a pretty big error.

These senior leaders in the room were my peers, and so I wasn't personally stressed about them having a bad impression of one of my team's presentations.

That manager was not incompetent in general. He'd made a judgement error. However, my peers rarely had interactions with that manager. Their limited experience with the manager was tainted by this poor presentation. He had an uphill relationship battle to climb because I hadn't ensured that he was ready for this very public presentation.

My lesson? As a manager, it's important to let people fail safely. You don't want to protect them from failures, because it will block them from learning. Yet you don't want them to fail in a way which damages their career.

After that event, I have always been careful to allow as much independence and failure as possible for employees, when it is safe. When the impact is large enough that a negative result would damage someone's career, I know it's my responsibility to protect them from themselves.

Another way to think about it is that your employees should be failing repeatedly in private, but look awesome in public.

The time when I fell asleep in a meeting.

This was pretty early in my career. I had bad habits left from my college days. I'd been staying up late watching TV or playing games. I thought I could handle being a little tired at work, but it was wearing on me.

One day we had a particularly boring meeting in a particularly comfortable room with the lights turned off. It was a big presentation with numerous senior leaders in the room. I fell asleep.

It didn't get me fired, but it upset my manager. It was embarrassing. Everyone had noticed. I felt stupid.

One interesting tidbit is that I really was stupid. Not getting enough sleep makes you less intelligent. Ignoring the falling asleep in the meeting, my lack of sleep was lowering the quality of my work. I was making larger errors. I was making less thoughtful decisions. I was missing obvious opportunities.

My lesson? My body needs to be taken care of, before I can execute properly. I don't like the feeling of failing. I want to be proud of myself at work, and that means bringing a properly functioning self to work. Eating and sleeping properly are basic requirements to doing my job.

During my years at Amazon, I've repeatedly seen engineers newly hired from college make the same mistakes I made. I'll see them come into the office like zombies, with their brains barely engaged in their tasks.

Imagine taking a pill which temporarily lowers your IQ by 15 points. Sounds terrifying to me. Yet this is what people are essentially doing when they stay up until 3am on a day before they need to use their brain. Less inspiration. Less drive. Less thoughtfulness. Your brain is what you were hired to use, and you're deliberately handicapping yourself.

I'd much rather have someone on my team work 6 hours and sleep 8 hours, then work 8 hours and sleep 6 hours. I'm confident that the 8-hour sleeper will do higher quality work, interact better with their co-workers, and add more value in the long run.