I joined Amazon in 2013. Two weeks in, I was convinced it was a mistake. I stayed for ten years.
I was hired as a systems development engineer in the Networking organisation. That’s the part of AWS where the Internet is physically built. People there talk about EBGP, DWDM, pigtail fiber (yeah, that’s a thing), AGG, and Core.
When I joined, I thought I was qualified. I could code, I understood systems, I had experience. I passed the 6 hours of back-to-back, face-to-face interviews.
I soon found out I didn’t just lack a bit of depth: I lacked the actual words to even ask basic questions. This wasn’t “I need to read up TCP/IP again.” It was “I don’t understand what the sounds you make mean.”
Everyone else seemed to get it. People were helpful, and very chill and very casual. People would whiteboard gibberish with great enthusiasm, and that would easily solve something I didn’t even realise was a problem. I sat in meetings understanding maybe half the words and a quarter of the concepts.
In the beginning, that was ok: after all, you don’t expect the new guy to understand everything. If you show up and listen in, eventually it will all make sense.
After week two of complete shock and confusion, a different thought moved into my brain though:
“They assessed the wrong stuff in interviews. They’re going to realise I don’t belong here. They’ll fire me after I moved countries a month ago, giving up everything. I’m so screwed.”
That’s what imposter syndrome feels like.
The advice that doesn’t work
I spoke to some people there and got some random advice: “Don’t worry, you deserve to be here. You earned your seat.” Sure, but I wasn’t worried about deserving. I was terrified about not delivering results.
The other flavour of advice came from outsiders, and it was worse. Basically, they said “fake it until you make it.”
In AWS? Yeah right. Bullshit is punished by your peers, and you only have one reputation. You can pretend you know stuff for about five minutes before you’re spotted as a fraud.
It felt like I had no options, so I just did the only thing I could think of: I started asking questions about everything and anything.
In meetings, I’d be the one going “sorry, please bear with me, but …”. I read wiki pages that made no sense and asked around for clarification. I remember having a whiteboard session with a network engineer woman from Venezuela who kindly explained to me some details of optic fibre networks just because I begged her to.
After a while, I started to recognise words, then patterns. I’d hear an acronym and think “oh, that’s the thing from Tuesday’s meeting” instead of “what the fuck is that.”
Then something happened: I started to get involved into meetings, conversations, projects.
That’s when the flywheel started.
The flywheel
Early on, context is expensive. You’re not helpful yet because you don’t know enough, and you don’t know enough because you’re not in the right conversations. It’s a deadlock.
The way out is to find something small you can own. Once you add some value, people start involving you more. Being involved gives you information. That information makes you more valuable, which gets you pulled into even more conversations.
It’s a compounding loop: contribution buys access, access buys context, context buys contribution.
At first you push the flywheel. Eventually, the flywheel pulls you.
What imposter syndrome is actually telling you
Here’s what I eventually figured out. Imposter syndrome is actually telling you two useful things.
First: that you’re aware of what you don’t know.
A lot of people walk around with blind spots they can’t see.
They don’t know what they don’t know. If you feel like an imposter, it means you can see the gap between where you are and where you need to be. That’s not a flaw. That’s information. You can’t close a gap you can’t see.
The people who never feel like imposters aren’t necessarily smarter or more competent. Sometimes they’re just less aware. They’ve stopped noticing what they don’t understand.
Second: you’re not alone.
It’s counterintuitive but it has proven true time and again.
For lack of alternatives, I asked questions I was sure were stupid. The really basic stuff: “Wait, why does that matter?” or “Sorry, can you explain what this thing does?” I felt bad for breaking the flow of the “big guys” by asking kindergarten-level details. Surely, everyone else already knew the answer to those questions.
But often, something weird would happen. People would nod. They’d engage. They’d say “oh yeah, good question” and actually discuss it, or they’d say “yeah, actually I was confused too”, or they’d disagree on the answer between each other because they thought it meant something different.
Turns out, half the room was wondering the same thing. They just didn’t want to look dumb.
The lesson imposter syndrome taught me is, when you’re the person willing to say “I don’t get it” out loud, you actually bring value. You voice the confusion that’s already there. And suddenly people relax. They think “Oh good, it’s not just me”, and then the conversation actually becomes useful.
Unlearn school
There’s this assumption that asking questions is a cost, and that you’re supposed to have done your homework and know shit. That’s because school teaches you a really bad habit.
In school, questions have right answers you were supposed to have studied. If you ask, it can feel like you’re admitting you didn’t do your homework. So you learn to shut up, nod, and catch up later.
In real life, that’s how projects die slowly. The “right answer” often doesn’t exist yet, and half the room is running on half-understood assumptions. If nobody says “wait, what?”, confusion doesn’t magically disappear. It just becomes implicit. And implicit confusion always comes back later as rework, bugs, or months of people building two different things.
The cost isn’t the question. The cost is everyone pretending they get it.
I became the person who asked dumb questions for everyone. Which is a weird reputation to have, but it turned out to be a useful one.
Ten years later
I spent about ten years in Amazon. I got promoted twice, I became a leader: of big programs first, and of people and systems later. I knew things. I became the guy who drew on whiteboards and explained the history to the noobs. But the habit of asking dumb questions stuck: unless I’m 100% clear (or at least I believe I’m clear in that moment) about something, I’ll just ask. Even if it’s basic.
Sometimes, senior people stop asking because they think they should already know. But “wait, why are we doing this?” is a perfectly valid question at any level. Often it’s the most important one.
Not despite the imposter syndrome. Because of it.
The caveat
Now, a caveat. Everything I’ve said assumes you’re in a place where this is actually possible.
Not all environments are like that.
I was lucky. AWS Networking was intense, but it wasn’t hostile. When I asked questions, people answered them. When I didn’t know something, nobody used it against me. The bar was high, but the culture was “let’s figure this out together,” not “let’s catch you being stupid.” That’s the kind of environment where people actually do their best work.
Some places are different. Some places punish questions. Some places have people who hoard information because knowledge is power. Some places have managers who treat your confusion as evidence you shouldn’t have been hired.
If you’re in one of those places, imposter syndrome isn’t telling you “keep showing up.” It’s telling you to get out.
Here’s how I think about the difference: productive discomfort makes you want to learn more. Toxic discomfort makes you want to hide. In a good environment, you feel dumb but showing up helps. In a bad environment, showing up makes things worse.
If asking a question gets you humiliated, that’s not a high bar. That’s a broken culture. Don’t confuse suffering with growth.
So, imposter syndrome.
The feeling is real. And it sucks.
But that feeling is also useful. It means you’re aware. And if you open up about it instead of hiding, you’ll probably find out you’re not the only one.
You’ll help yourself and everyone else in the room.
You’re not the only imposter. You’re just the only one being honest about it. And that honesty, it turns out, is worth something.