How to Both Embrace and Defeat Imposter Syndrome

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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It’s impossible for tech people who grew up in a tech area (Seattle, most big California cities) to understand what it was like being a tech person from the Midwest.

I literally wore a suit to my Amazon interview. Which, as a person from Illinois, sounded like a reasonable plan. You want to show that you’re serious, so you dress up.

And then I walk into my interviews, and people say, “Oh! You’re the guy with the suit!”

“Why yes, I am”, I thought. And I deeply regret that choice.

But beyond the culture differences, there’s a world of best practices you’ve missed when you had no skilled co-workers. My friend and I spent years building technical solutions straight out of college, with zero oversight.

Clearly, I figured things out, but my base knowledge of how large-scale systems are built was filled with holes.

I started my new job at Amazon straight out of the Midwest, and it was rough.

I certainly started out excited. Everything was so new and fun to learn. Engineers could solve problems in a few minutes it would have taken me days to figure out. “Give me 10 minutes, I want to quickly throw up an admin panel for this new service, and then we can grab lunch.” - Excuse me? 10 minutes?? Yes, it turns out that experienced engineers with a bunch of infrastructure can do amazing things.

But after the excitement, I began to feel seriously confused. And because of that confusion, scared for my job security.

The pace was faster than I was used to. Again, tasks I thought would take days were expected to be knocked out. What I thought were big assignments were small side tasks.

And the systems were incredibly complex. I’d been managing a few servers with a couple of services, a database, and a UI. My new team had a dozen services with hundreds of servers, UIs, admin panels, Wikis, documents, changes, and pager rotations. And don’t forget the more than a dozen teams I worked with daily, literal hundreds of services relying on ours or ours on theirs.

It seemed like the other managers were totally under control, and I was silently lost, and starting to have a panic attack inside my head.

I can clearly remember the worst moments of panic. I would close the door to my office, pretending to be busy. I couldn’t handle yet another person entering my office, and asking for decisions I didn’t feel qualified to make. I could see my peer managers walking around with smiles on their faces, calmly answering questions. I felt that I didn’t belong.

I began to imagine what searching for a new job would be like, with just a few months of Amazon experience on my resume. Should I consider taking my old job back?

Clearly I got past this. But not everyone does.

Imposter Syndrome is the extremely loud and persistent voice in the back of your mind yelling, "You're not good enough!", "You don't belong here!", or "Everyone else is better at this!" It’s a painful feeling.

However, it’s also inevitable if you’re interested in improving yourself. So rather than avoid it (which would actually be a pretty bad thing), I have some thoughts on the topic.

Imposter syndrome has an uncomfortable level of truth to it

I don’t think you should deny imposter syndrome and tell it that it’s a big fat liar. I’ve seen people try that.

“I feel so incompetent in this new role!”

“No, that’s just imposter syndrome talking! You’re great!”

Except they’re not. At least not yet. And I think pretending that you (or someone else) is better than you are is dangerous.

When we change companies, or try new things, or take on new roles - it can be scary. And we’re expected to do uncomfortable things. Our co-workers will likely do them better. There will be occasions where we’re expected to do something, we’ll try, and we’ll fail. We’re justified in our fears that we might fail. Because we really might!

As I said earlier, when I joined Amazon, I came from the Midwest. And that means I’m allowed to make fun of the Midwest. I didn’t have the same engineering background. I hadn’t touched anything remotely approaching our scale. I hadn’t managed a team as large as the one I joined.

We don’t feel imposter syndrome when we’re working on tasks we’re comfortable with. I remember in those early months being excited when someone asked me a question I could answer. Perhaps they asked about something an engineer had mentioned just earlier that day.

But those were rare. When we’re in the middle of something new, we feel imposter syndrome when we legitimately don’t have that expertise. We fear that others might discover our gaps in experience, knowledge, or skills. And that fear is justified...