Waiting for the other shoe to drop: How I overcame Imposter Syndrome


I spent much of my early career waiting for the other shoe to drop. Any minute, I thought, someone is going to tell me I don’t know what I’m doing – that I’m a fraud, a charlatan, a bounder. (I tend to revert to old-timey insults when I’m berating myself.) “The jig is up,” I used to say, quietly in my head and never, thankfully, out loud in meetings. 

When this thought landed, it was like a tornado of fear in my stomach and the center of my chest.

I remember a time when I was part of a business pitch with the president of the agency I worked for in Chicago. It was a technology-heavy piece of business and I really did not know what I was talking about. My face was hot and my scalp was itching with panic. The worst of it was that the president was a sweet, soft-spoken man, and smart – so smart that he could see I was badly bullshitting my way through this presentation. 

Only decades of time has made this possible for me to discuss openly, because in the moment I wanted to run from the room never to be seen or heard from again. It’s because I had two kids at home and no one helping to pay the bills that I wouldn’t let myself budge from the chair and forced myself to keep saying words, one after the other, in the hope that something would start making sense. I needed the job, the paycheck, the health insurance, the stability. I needed to seem like I belonged at that table, when I truly didn’t. “Fake it till you make it” is a thing that people like to say about situations like this, which sounds so breezy and fun, when it’s actually a miserable journey of feeling your way across a dark room, banging into a lot of big, hard, heavy furniture as you creep along, until finally you begin to see a pinprick of light that you latch onto and hope it grows. Your eyes adjust and you start seeing shapes and colors and objects and oh you get it now, right here, this is the way. It slowly gets clearer, but it is a grueling walk. 

Later, after years of experience in a variety of office jobs and creative jobs and a few executive-level jobs, this fraud-fear became more of a quasi-anxiety – something that dropped in occasionally and half-heartedly haunted me. 

that felt like progress. 

And then later (much later) it became my own little inside joke. Sort of like a catchphrase I’d say to myself, whenever I was in charge of a big-deal agency pitch or a complex writing project – like the time I had to pitch to Microsoft one week after I was hired to be the VP of Brand Strategy at an advertising agency in Los Angeles. Or the time before that when I was still living and working in Chicago and a client asked me to write a white paper on commodities. 

A white paper, for those of you who don’t know, is a detailed, well-researched overview of a specific topic – a report filled with insights and fresh thinking and a singular point of view. As I was saying “Yes, of course, I can do that” to the person who was asking me if I could write 5,000 words on something-something-something commodities, I was holding my phone in the crook of my shoulder against my ear, while simultaneously googling: What is a commodity?  

It was moments like these that the voice inside my head would say, “The jig is up!”…and then I’d sit myself down and learn that commodities are things like corn and gold that are traded for money, I think. 

I’ve now fully retired this catchphrase, and that fact that I’m not dogged by the anxiety it carried pretty much sums up where I am today — confident that I know what I know, curious about new things I want to learn, and absolutely sure that what I don’t know and what I’m not curious about isn’t for me. I no longer try to fit myself into a shape or a description that doesn’t match who I am and what I do. A lot of personal and professional growth has brought me to a place where I am completely comfortable saying “I don’t know what that means” or “I’m not sure how to do that.”

And that’s what I call freedom. 

All of this has made me uniquely empathetic to my clients who struggle with “Imposter Syndrome” and anxiety about how good or smart or special they are. I have a client who is poised on the brink of expanding her beautiful brand and scaling her delightful offerings, and almost every call we have ends in one or both of us shedding tears… of mutual recognition, of inspiration, of camaraderie. It’s that wonderful feeling of – YOU SEE ME. So I see myself. And now I know I can do this. We’re in this together.

Shine the light on your Imposter Syndrome

During all those years that I was making things up out of thin air, I learned a few invaluable lessons that I try to pass along to my beloved clients:

  1. You are allowed to invent yourself over and over and over again. 
  2. You have the freedom to try something, change your mind, and then go off in a completely different direction. 
  3. You are capable of learning new things, and with lightning speed if you put your mind to it. 
  4. You don’t have to be good at things that don’t matter to you, and you don’t have to do things you’re not good at. 
  5. You can spin your Imposter Syndrome into gold by thinking of it as an indicator that it’s time to dive into the deep end of this exciting thing you’re trying – and make it your own. 

Here’s the truth: We are all “imposters” at one time or another.

Anyone who has ever taken a new job is winging at least parts of it. Anyone who has ever moved to a new city spends those first few days trying not to look like a tourist. It’s human nature to want to feel like you “belong” – and before long, you do. You get good at your job and start speaking up in meetings. You remember streets and learn the names of everyone who works at the corner bakery. You settle in, and claim your new space. 

The same is true for entrepreneurs and brand builders. When you claim your space, it’s yours. The journey to “being there” is nothing more than a mindset…a decision that only you can make. A light only you can turn on.