Thursday morning, rush hour, the A train headed to Manhattan. I’m just going to be super transparent here—there was a man who had gotten on the train standing next to me who happened to be, by any standard, really handsome. On any normal day, I would glance up every now and then, text my friends that I have a new subway crush, and then disappear into the swarm of New Yorkers headed to their destinations. However, this wasn’t a normal day. I found myself fully engaging in a self-inflicted internal argument. There was something in me that felt curious…curious enough to do something about it. So, like any reasonable adult, I brokered a deal with myself. The deal was this: if there is a pen in my bag, I’ll give him my number on a piece of paper. If not, it’ll be chalked up to a missed connection. Was there a small part of me hoping that there wouldn’t be a pen in my bag? Absolutely. Was there a pen in my bag? Absolutely. I never have a pen on me.

I am, after all, a woman of principle. I held myself to my ultimatum. There I was, tearing off a piece of a Whole Foods receipt, clumsily jotting down “Stella” and my phone number.

Mind you, I have two stops left until my destination—so I’m stuck holding this piece of paper. Awesome. After what felt like ages, the A train roars out of the tunnel and pulls up to the platform. Before I could even talk myself out of this interaction, my hand was already outstretched, handing the piece of paper to the man. “Wait, this is for you,” I say. I hadn’t thought about the speaking part (ha, ha).

He smiled (confused), I smiled (also confused). The doors shut, the train barreled to its next stop.

I did indeed disappear into the swarm of New Yorkers headed to their destinations—but this time, with a sense of gratification that gave me pause. As I was replaying the interaction in my mind (probably twenty times), the excitement didn’t come from the prospect of hearing from this man (albeit, a fun byproduct). It came from something else entirely. Feeling, being, an active participant in my own day—in my brain. Embracing discomfort on my own volition.

Embracing friction, even if it’s within myself.

Why did something that could be deemed a humiliation ritual put me in such an optimistic mood? After letting this question marinate for a minute, it hit me. I experienced something that wasn’t served up to me on a silver platter by The Algorithm. There was nothing contributing to that interaction that had anything to do with the tech wizards that eat our data for breakfast. It ultimately came down to existing at the same time and same place as this individual, and seizing the moment.

I don’t like to make sweeping generalizations, but for the sake of this story, I will—so bear with me. Gen Z is (generally speaking, okay) a self-declared socially anxious generation. And I would argue that it has crippled our ability to create moments of connectivity amongst ourselves. I don’t know that I fully understood the degree to which Gen Z has consented to outsourcing our thinking until I experienced this moment. And I would reason that, as a result of this outsourced thinking, our DOING has been squashed. For lack of a better word.

Later that day, I wound up dissecting the concept of “getting to the grey” with Amy. And if you’ve listened to the podcast that I co-host, The Grey Area, you’ll understand that not everything is black and white—grey is a color, too. It’s the proverbial middle-ground that grants us permission to change our minds, exercise critical thinking, and experience a range of discomfort that makes the human experience richer. Good old-fashioned nuance. They don’t make it like they used to—but this doesn’t have to be the case. It does, however, require getting uncomfortable on purpose, which you might instinctively and viscerally reject. I understand this—we all love to be cozy. But we might be so cozy that we are beginning to err on the extreme end of cabin fever. And amazing things can happen when you get outside.

I typically don’t wrap these articles with a call to action, but I would like to now. If you’ve listened are a fellow Gen Zer, or if you know a fellow Gen Zer, I would urge you to do something this week that extracts you from The Algorithm. Smile at someone on the train. Tell someone you like their shoes (granted you actually like their shoes). Ask someone a question. Shoot your shot! I would wager that you might end up having an interesting conversation that you may not have otherwise had. Maybe you will be shrugged off, maybe you will learn something new. But one thing is for certain: you will walk away from the experience with the knowledge that you did something that made you feel like you have a pulse.

If you haven’t already, I would highly encourage you to pick up a copy of Amy’s book, Almost Reckless: A Creative and Pragmatic Approach to Taking Risks. It’s an incredible guide for codifying your principles to help you extract yourself from the algorithm when the moment calls for it. I’ve read it myself, and it is genuinely a one-of-a-kind guide to sharpening your internal measuring stick for taking risks.

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.

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