Your Imposter Syndrome is Trying to Tell You Something

If you listen closely enough, it might actually help you.

I want to share a story from the very beginning of my career at Tibi. I was 21 years old and I worked on our public relations team with our then-head of PR. She was an incredible teacher and colleague, and I remember watching and listening in awe when she would speak. She was sharp, articulate, polished, organized, and had something that, back then, I was incredibly jealous of: experience. She had been at Tibi for a very long time before I weaseled my way into this office, and it showed. When Amy would ask her a question about a process, she would reply with the utmost composure and say, “Well, historically, we would do XYZ…”

I must have heard her say some version of this on hundreds of occasions during our time working together, and every time she said it, it held validity. She owned that sentence and the information that it held—and everyone knew that she could be relied on as a trusted source of accurate information. I wanted to be relied on as a trusted source of accurate information, too.

One day, Amy asked me a question about a process we were ironing out for an upcoming project. I began to say, “Well, historic-”, and before I could let the words finish spilling out of my mouth, Amy stopped me.

“What do you mean, ‘Historically’?”

“Well, I just know that in the past we-”

“But what do you mean by ‘in the past’? You weren’t there.”

I remember so vividly how I felt in that very moment—like I had been found out. Like the jig was up, she saw right through the professional facade that I was so painstakingly trying to portray. Except that’s not actually what happened; Amy is the one who hired me in the first place, and she knew that I was fresh out of school and didn’t have any prior experience. It was me who I was miserably failing to fool—not her. Humbling.

It was this very moment that I had to look Imposter Syndrome in the eyes. I think that just about anyone can relate to some version of this experience, no matter what age or stage of life you’re in—you walk into a room, you look around, and slowly (or quickly) realize that everyone there knows more than you do, so you fake it till you make it. Or, like me, you fake it and don’t make it—at least, you don’t make it in the way you thought you would (in the grand scheme of things). But can I let you in on a secret? As someone who was very recently let in on this secret myself?

Once I became friendly with the three words that scared the living daylights out of me (“I don’t know”), I began to make it to the place that I was actually meant to make it to—not the place that I was trying to fake it to. And while I’m very much still on this path, I’d like to believe that the outcome starting to materialize is much better than the alternative.

In discussing this very topic on a recent episode of The Grey Area Podcast, a realization hit me. I spent years arguing with my Imposter Syndrome to find out that it might not be the enemy I thought it was—it’s certainly not kind or tender by any means, but if you learn to decode what it’s trying to tell you, if you try to understand it, you might find yourself thanking it from time to time. On one hand, it was the perpetrator of anxiety and insecurity at seemingly the worst possible moments, and on the other hand, it’s the very thing that catalyzed so many monumental shifts in my career—shifts that have made me a better employee, friend, and person. Ah, the classic “frenemy” trope. How sweet.

I think about the sheer amount of effort that I put into trying to emulate someone else’s path, and the never-ending well of frustration that came with it. While I believe that I’m too young to have regrets yet, I do wonder where I would be if I redirected that effort into figuring out where I was supposed to be headed. Walking a mile in the wrong pair of shoes can give you blisters. And now that mine are starting to scab over (this sounds gross, but I mean it in a nice way), I want to share two things that I didn’t know then, but know very well now.

1. When you admit you don’t know, and become comfortable with admitting there is a gap between you and knowledge, the path to closing that gap becomes oddly clear.

2. If you listen to your Imposter Syndrome rather than succumbing to it, it can actually serve as a guide leading you to where you’re meant to be, rather than where you’re trying to go. Lean into what you do know, and seek out what you don’t.

If you read this nodding your head along the way, and I’m speaking especially to my fellow Gen-Zers, I encourage you to read Amy’s new book, “Almost Reckless” (buy here). I can speak to this experience only up to this point—but this book offers insight over the course of decades, from someone who rewrote the rules on finding your own path. Having worked for Amy for the last five years, I can speak from personal experience that the principles in her book check out in a super real way—many of them played a major role in my own professional development, before they were ever bound in a book: the sooner you learn to identify what success means to you, the sooner you figure out how to codify what your principles are, the sooner you’ll be on the path that’s meant for you—even if it makes sense to no one but yourself.

Stella, I have to add my thoughts here. My POV, ok? - Amy

There’s a saying that when you are hiring a sales person, you should always look to see what type of car they drive. What they’re driving should be a grade above what they can afford. Why? Because it means that they’re striving for the next level, they’re hungry. If they’re driving a clunker, they settle; if the car is a huge stretch, they’ll cut corners. I find that the hallmarks of a great team member, every time, is that they’re a bit of an imposter of sorts - we all are striving for the next level. They think they’re just a little better than they actually are in that moment (confidence), they say things they regret (enthusiasm), and most importantly, they recognize when they don’t know something (humble). Clearly, to have all three in play, one of these things will always be compromised. And that’s where a team member that is principled, logical, clear headed excels - it’s a dance, moving forward and backwards, some missteps, some big strides. Moving together to the same beat, or shared objectives, as it were.