On Imposter Syndrome
This is going to be a hard one. Imposter syndrome is something I’ve wrestled with my entire career, and I suspect many of you have too. After 25 years in tech, multiple career transitions, and countless “oh shit” moments, I’ve come to realize something counterintuitive: imposter syndrome might actually be a feature, not a bug.
But I’m getting ahead of myself. Let me start by unpacking what this beast actually is, where it comes from, and why it’s simultaneously the thing that’s held me back and pushed me forward throughout my career.
What Is Imposter Syndrome, Really?
At its core, imposter syndrome is the gap between what others think you know and what you actually know, or more accurately, what you believe you know. It’s that nagging voice that whispers “they’re going to find out you don’t belong here” just when you’re starting to feel comfortable.
But here’s what makes it especially insidious for those of us in tech: our industry literally requires us to be constantly learning. The moment you feel like you’ve mastered something, the ground shifts. New frameworks, new platforms, new paradigms. That gap between perceived and actual knowledge? It’s not a bug in your psychology, it’s a fundamental characteristic of working in a field that reinvents itself every few years.
How It Manifests
For me, imposter syndrome has shown up in visceral, physical ways. The worst is the mind blank, that terrifying moment when your brain simply stops processing and you’re left standing there, exposed. I know my triggers now:
- Large, open forums where the audience might be judging rather than learning
- Delivering content I don’t deeply own or understand
- Situations where I feel the weight of others expectations
Over the years, I’ve learned to either avoid these triggers or over-prepare to the point where I can manage them. But it took me far too long to develop these coping mechanisms.
Where Does It Come From?
Looking back, I think imposter syndrome in tech comes from a few places:
The “fake it till you make it” culture - We’re often encouraged to say yes to opportunities and figure it out later. This works, but it also means you’re constantly operating at the edge of your competence. Careful to avoid the Peter Principle!
The curse of growing awareness - Paradoxically, as you become more experienced, you become more aware of what you don’t know. The more you learn, the more you realize how vast the unknown territory is. See the Dunning-Kruger Effect
The comparison trap - In tech, you’re always surrounded by people who seem to know more than you in some area. The full-stack developer who also knows machine learning. The architect who can still code circles around you. The consultant who can talk to CEOs without breaking a sweat.
My Journey: A Chronicle of “Oh Shit” Moments
The Stage Freeze (2008)
I remember the exact moment imposter syndrome first truly hit me. I was with Microsoft, traveling the world as part of a Unified Communications specialist group, running training events across APAC and Europe. We’d done dozens of events, and on the very last one back in Sydney, I decided to deliver a session I hadn’t presented before. I’d watched others run it multiple times, how hard could it be?
Halfway through, I paused on a slide and realized: I don’t actually understand this.
It hit me like a ton of bricks. I froze. One of the other specialists had to step in to rescue me and finish the session. That was my first real “oh shit, I shouldn’t be here” moment, and it left scars. For years afterward, I could handle small meetings and customer conversations, but put me in front of a large audience? Forget it.
This probably held my career back significantly. While others were building their personal brands through conference talks and public presentations, I was hiding in the relative safety of one-on-one interactions.
The Accidental Leader (2012)
My next major imposter moment came at Dell. I’d helped sell a multi-million dollar deal with a government agency and somehow found myself as the lead architect, building a team of 25 people and delivering a time-sensitive project in less than 12 months.
The thing is, I didn’t realize the gravity of what I’d taken on until about six months in. I’d gone from being “just a normal techo” delivering my own work to being responsible for an entire team and program. I wasn’t experienced or qualified for that function, I had to learn all the non-technical leadership stuff the hard way.
This became a pattern for me: excitement overrides any rational assessment of qualification at decision time. I see an opportunity, I jump in with both feet, and only later do I realize what I’ve gotten myself into.
The Cloud Transition (2016)
When I joined AWS, I thought I knew what I was getting into. I’d been at Microsoft during their early cloud efforts, and I’d led a team building private cloud for government. How different could public cloud be?
Very different, as it turns out.
I was an “infrastructure guy” with no real understanding of how to build software or distributed systems, let alone how to do it in a public cloud. I had somehow gotten through the interview process (largely thanks to recommendations from people who’d already made the jump), but I was completely out of my depth.
Those first couple of years at AWS were a masterclass in drinking from the firehose. I was lucky to be in a small team of smart people, and the company still had that startup feel where you could make your own way without big-company overhead. But man, did I have a lot to learn.
The Breakthrough (2020)
It wasn’t until COVID hit and I transitioned into a global role that I started to figure out how to manage my fear of public speaking. Working 100% remotely, talking to people around the world I’d never met, it gave me a chance to present pseudo-anonymously. Video calls became my training ground.
When I moved to Geneva for the UN role, I eventually developed a GenAI training program specifically as a way to force myself back on stage. The key difference? I owned this content. It was mine, not someone else’s package I was trying to deliver.
That’s when I learned a crucial lesson: you can only fake expertise so much. Unless you’re deeply connected to the content, you’ll never truly own it or come across as an expert. Creating and delivering my own material gave me control and confidence I’d never had before.
Reflections: What If I Had My Time Again?
Looking back, especially at that 2008 stage freeze and the years it held me back, there are things I’d do differently. I should have:
- Found and used mentors more actively - Back then, I felt like I needed to keep my struggles to myself and project confidence. Opening up earlier would have accelerated my growth.
- Gotten back on stage sooner - Avoiding my triggers for years only made them stronger. Confronting them earlier would have made a massive difference over the following 15+ years. I wish I’d known about about the Yerkes-Dodson Law earlier, putting myself under a little more pressure might have helped.
- Been more compassionate with myself - I spent so much energy hiding my insecurities instead of accepting them as a normal part of growth.
The Unexpected Gift
Here’s the thing though: as painful as imposter syndrome has been, it’s also been one of my defining traits that helped me achieve what I have. Could I have achieved more without it? Maybe. But it also:
- Made me super self-aware
- Helped me recognize and appreciate the challenges others face
- Kept me humble (as opposed to the “I know it all” techos I often encounter)
- Drove me to constantly learn and improve
I think back to 1999 when I found an ad for MCSE training in the back of the paper. When I showed it to my dad, he said, “If you go into IT, you’ll be learning new stuff for the rest of your life. Do you really want to do that?”
That sounded exciting to me! So I sold my motorbike (which I’d bought a year earlier for $8k), paid $6k for that course, and my career (and life) snowballed from there. That constant learning, that sort-of feeds imposter syndrome, has also been the source of my professional success.
Making Peace with the Impostor
Today, at what might be the tail end of my career, I’m very aware of what I know and what I don’t know. I can see it in others too, which helps me engage in ways where I feel in control and confident. I:
- Know my triggers and either avoid them or over-prepare
- Choose my audiences (people who want to learn rather than people who want to look better than me)
- Accept that the gap between perceived and actual knowledge is permanent in our field
For Those Still in the Thick of It
If you’re reading this and recognizing your own struggles, here’s what I want you to know:
You’re not alone - That senior architect who seems to have it all figured out? They’ve had their own “oh shit” moments.
The pattern is normal - That cycle of excitement → commitment → “what have I done?” → frantic learning → eventual competence? That’s not a flaw in your approach. That’s how growth happens in tech.
Find your people - I waited too long to be vulnerable with mentors and peers. Don’t make my mistake.
Own your content - The difference between delivering someone else’s material and your own is night and day. Invest in deeply understanding what you’re talking about.
Imposter syndrome might be your edge - While others rest on their laurels or become those insufferable “I know it all” types, your doubt keeps you learning, growing, and empathizing with others who are struggling.
The Bottom Line
Imposter syndrome isn’t something to be cured, it’s something to be managed and even appreciated. In an industry that requires constant learning, feeling like you don’t know enough isn’t a bug; it’s a feature that keeps you relevant.
The key is learning to use it rather than being paralyzed by it. To jump into opportunities despite the voice that says you’re not ready. To be vulnerable with others about your struggles. To recognize that everyone else is figuring it out as they go too.
Twenty-five years in, I still get that “oh shit” feeling when I take on something new. The only difference is that now I recognize it as an old friend, one that’s telling me I’m about to grow.
And isn’t that why we got into tech in the first place?