The Creative Pragmatist: Insider Report

Your Imposter Syndrome is Trying to Tell You Something

Stella Pyles — Sun, 17 May 2026 14:30:01 GMT

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.

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.
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.

What Are Your "Stealth" Skills?

Stella Pyles — Sun, 29 Mar 2026 13:51:12 GMT

One day, when I was five years old, my older sister Sydney and I were left at home to be babysat by my grandmother. She was a notoriously cranky woman (before you gasp, this is a fact she would endorse), so when I relentlessly begged her for a glass of Hawaiian Punch, her patience quickly deteriorated. After asking ten too many times, my sister and I were sent up to our shared bedroom to “take a nap and settle down”. What my grandmother didn’t realize is that idle minds make for mischief—and Sydney and I were clever little things.

Hell-bent on getting that Hawaiian Punch, we devised a plan.

The kitchen was right off the laundry room, which gave us a window of opportunity to carry out our punch heist. We took a laundry basket, filled it with enough clothes to conceal a jug of fruit punch and two glasses, carried it down the stairs, and looked at our grandmother with wide, innocent eyes—we were being dutiful children and getting a head start on laundry for our mom…duh. Logic would suggest that five and seven-year-olds don’t do laundry, but thankfully, logic wasn’t invited to the party that day. We made pretend footsteps to the laundry room, hoisted each other up to get two glasses from the top cabinets, and secured the Hawaiian Punch.

I’ll let you guess what happened when my mom got home and found us in our bedroom with big red stains around our mouths and a half-empty jug of fruit punch, but that’s besides the point. I share this story because it’s the first memory I have of learning that sometimes you have to be scrappy to get the job done.

When I was 14, I got my first job as a cashier at Chick-fil-A. I grew up in the South, so hearing the words “My pleasure" wasn’t necessarily a rarity, but actually saying them myself felt like something else entirely—especially when it was being said to a woman shuffling up to the register in the midst of dinner rush holding a single chicken nugget wrapped in a napkin claiming that it was “too small to be considered a nugget” and demanding that we give her one. single. replacement. nugget. For the record, I offered her a new 6-count nugget on the house, which she refused. She literally just wanted one nugget. The moral of the story here is twofold: nuggets are in the eye of the beholder, and the customer is always right (*unless they aren’t).

Eventually, when I had learned about the concept of earning tips, I moved on to a job waitressing at Steak ‘n Shake. I was 16 years old at the time, and had no prior experience waitressing—but with an hourly pay of $2.30 and money on my mind, I was determined to leave with the biggest tip payout of each shift. On a typical day, I buzzed around the restaurant in my bowtie and apron, taking orders and forgetting the odd table or two (waitressing is no joke, IYKYK). But I remember one day in particular, a party of 8 walked into the dining room, and the hostess ushered them to a table in my section. I trotted over, flashed a smile, and started rattling off facts about new items on the menu—and it wasn’t till I looked up from my little notepad that I noticed that they didn’t hear a word I said. One of the individuals at the table kindly shared with me that they were all deaf. I’ll never forget their incredible patience and kindness as I collected their orders and served their table that night—an excellent lesson in communication and humanity in my early teenage years.

Though on the surface these anecdotes might seem random, they’re more relevant than ever—for me, at least. In the same way that they say, “You don’t know what you’ve got till it’s gone,” the truth is: sometimes you don’t know what you’ve got till you’re faced with a scenario that requires that very thing. A “stealth” skill, if you will. The skills that you’re pocketing along the way without even realizing it.

When I think back to some of these eras in my life, particularly my teenage years working in restaurants, I remember how I felt in those moments. To be honest, I felt far from where I wanted to be. I was a teenager in a very small town who knew she wanted to live in a big, shiny city and work in fashion—and my perceived* lack of opportunity made me feel as though that dream would never convert to reality. (*I say “perceived”, because the opportunity is almost always there, you just have to find it—or, create it).

But in hindsight? These experiences played an enormous role in shaping who I would become when I was ready to show up at Opportunity’s door, saying, “Let me in, please. I brought dessert!” I use these skills every single day, and I have gratitude for every bumble, hiccup, and red Hawaiian Punch stain that sharpened the skills in my arsenal, without even realizing it.

Maybe you relate to these experiences, or maybe you’re like Amy, and you’ve become a master storyteller as a byproduct of deceptively tossing the newspapers from your paper route into the woods to smoke cigarettes at age 11 (true story, and a legendary one—you can read more about this in her new book, “Almost Reckless”).

I’m not quite established enough in my life and career to be able to have big “I wish I knew ______ when I was young.” But I will say this: if I did have the opportunity to sit down across from my teenage self at a Steak ‘n Shake, I would tell her not to write off the experiences that feel like passive sidequests, and to try to pluck out these learning moments in real time. And if it were me in the present time, I’d make sure to emphasize the importance of putting down the phone, leaning in, and being present. Because more often than not, when you embrace the detours, you’ll find yourself learning things that you never would have otherwise—and you’ll be better off for it.

If this resonates with you at all, I’m excited to share our new podcast, The Grey Area, hosted by me, Gabe, and Matt from the creative team here at Tibi. All Gen-Z, figuring things out. Whether you’re Gen-Z, you know someone who is Gen-Z, or you’re just plain curious—we have really good conversations guided by concepts and principles outlined in Amy’s new book that prompt us to think beyond the black and white and embrace ambiguity. There’s really valuable information in there about seeing all these moments in life, as arduous or mundane as they may seem at the time, as dots that we’re collecting that eventually come together to create our big picture. We certainly don’t have all the answers, and we won’t always agree, but we do know that when we open the floor to good, honest discourse, good things happen.

I encourage you to read the book Almost Reckless and join along in our podcasts. I’d also like to hear what jobs populate your resume, but the skill set acquired goes way beyond the tasks listed, like “put hamburger in bag and smile.”

Friends with Hot Pockets.

Stella Pyles — Mon, 02 Feb 2026 18:07:19 GMT

The other day, I was minding my own business in our office kitchen when I heard a rustling and crunching that—if I didn’t know any better—I would assume was from a forest animal foraging for nuts and leaves before hibernation. I turned around to find not a squirrel, but my boss—seated contentedly at the communal table, artfully layering pieces of cheese…

Have You Nailed Everything But the Hem?

Stella Pyles — Wed, 07 Jan 2026 18:18:40 GMT

When: October 2025
Where: The 6 train at around 2 PM—heading back to the office with Amy after filming an episode of the Off You Go Podcast (streaming here now, by the way).

To my surprise, the train was only half full—a rare occurrence for a weekday afternoon. We snagged seats along the wall and waited for the doors to close. I opened my mouth to begin r…

It Takes Both Ends to Hold a Rope Steady

Stella Pyles — Sun, 23 Nov 2025 16:40:27 GMT

Someone shared a quote with me recently, and it hit hard—the way a quote does when you feel it so intrinsically. But where does that feeling come from? We don’t all just pop out of the womb vigorously nodding our heads in agreement with one another. I want to share with you my thought process here—how I connected the dots, and why this metaphor about a …

Practice Asking Questions

Stella Pyles — Mon, 10 Nov 2025 17:07:41 GMT

A few years ago, around the holidays, my family and I went through a big box of old home videos. I’m one of four girls, you can imagine the endless reels of dress-up, performances , and admittedly, some fights over American Girl Dolls or something of that sort that my mom was forced to sit through and film. In one of the videos, my older sister owns the…

The Problem With the Fashion Ick

Stella Pyles — Thu, 14 Aug 2025 16:56:30 GMT

I got my first job when I was 14 years old. My first three jobs ever were at restaurants—and if working in the food industry for a number of years taught me anything (and it certainly taught me a lot), it was that everyone has different tastes. Even more so, it taught me that no matter what someone orders, the correct thing to do is smile and say, “Okay…

Where is the Line of Being Too Online?

Stella Pyles — Thu, 31 Jul 2025 15:12:54 GMT

I write a lot of copy.

In fact, a sizeable chunk of my day-to-day life is spent writing copy. Long-form, short form, social media captions, you name it. To most people in my field, writing copy is likely viewed as a monotonous task—I’ll admit that some days, when the words just aren’t flowing, it can certainly feel that way. Outside of work, my social ch…

Is "Core"-core in Anymore?

Stella Pyles — Wed, 02 Jul 2025 16:11:55 GMT

Amid a heatwave in New York, there I was: sitting at my desk, trying to muster up enough heat-exhausted brain cells to form a singular thought. Most of my office is traveling right now, which means it’s almost completely silent—a stark contrast to the near-constant chatter that bounces off the walls at Tibi HQ. Knowing this would be the case, I carved o…

The Heatwave Solved Here: The Tibi TRR List

Stella Pyles — Wed, 25 Jun 2025 17:18:07 GMT

This week’s forecast in New York City is scraping the triple-digits, which means that getting dressed will be an act of survival. Dramatic, maybe—but it’s true. Sure, we all need to refresh our seasonal rotation now and then, but I’m not advocating for going buck wild stocking up on what basically amounts to scraps of fabric just to beat the heat. I’m p…

Embrace Ambiguity: Not Because You Have To, But Because You Want To

Stella Pyles — Fri, 13 Jun 2025 16:01:52 GMT

Exactly four years ago, I resigned from my first job out of school—before even stepping into the office—to join Tibi full time.

I began my career at Tibi as a Public Relations intern back in early 2021 (I shared my internship experience here—it’s a good read), and we all know that I thankfully ended up back at Tibi for the long haul, but it didn’t happen…

2 Creative Pragmatists Walk into the Subway

Stella Pyles — Fri, 06 Jun 2025 16:39:16 GMT

If you regularly ride the New York subway, or if you’ve been on the internet in the last month, you might have seen chatter amongst fellow commuters about glitches with Omni. For non-New Yorkers, Omni is the system that the MTA has been implementing instead of a good old-fashioned MetroCard. Glitches are not exclusive to Omni software; however, they are…

Internal Re-calibration with Personal Style

Stella Pyles — Sun, 13 Apr 2025 16:22:27 GMT

My friends and I have a phrase we lean on a lot—especially when life throws something unexpected our way. Whenever one of us stumbles through a tough moment or learns a hard-earned lesson, we say, “It’s my first time being alive.” Over the past couple of years, I’ve realized just how often those words echo through my day-to-day. At 26, I’m the oldest I’…

Guessing Your Interior Style Based on Where You Land on the CP Scale

Stella Pyles — Tue, 08 Apr 2025 13:51:06 GMT

The Creative Pragmatist Scale has been perfected over the years. Whether highly creative or dogmatically pragmatic, we move along the scale. Some days we’re balanced right in the middle, other days has one end pulling us, magnetic-like, further to one side. It’s become second nature to us, and to so many of you, to move seamlessly along the scale depend…

My Year at Tibi

Stella Pyles — Mon, 30 Dec 2024 22:53:50 GMT

I don’t think I’ve ever truly set a New Year’s resolution—at least not one that carried any real weight for me. If I did, I certainly don’t remember it. However, I’ve always loved the New Year’s holiday. There’s something undeniably exhilarating about the idea of a fresh start. When the clock strikes midnight on December 31st, I used to like to imagine …

4 Gift Guides For 4 Types of CPs. Here.

Stella Pyles — Wed, 11 Dec 2024 19:43:35 GMT

I’m a sucker for a good gift guide. Every holiday season, I dive into countless lists, hoping to find the perfect gift ideas. But here’s the catch—I’ve yet to come across a guide that truly speaks to the very specific groups of people that Creative Pragmatists find themselves shopping for. As CPs, we approach gifting much like we approach our personal s…

How to Keep Your Head on Straight

Stella Pyles — Wed, 27 Nov 2024 17:31:00 GMT

My eighth-grade English teacher didn’t teach much English. While he certainly understood the value of proper grammar—like when to use a semicolon versus a period—he believed life lessons would serve us better in the long run. Rather than adhering to the curriculum, he used his hour of our captive attention to explore ideas that truly mattered. One of th…

Please, Just Put On a Blazer.

Stella Pyles — Tue, 05 Nov 2024 18:01:08 GMT

I’m going to hold your hand when I tell you this: you’ve got to put on a blazer. The job market can be daunting for recent graduates, and let’s be honest—shows like Emily in Paris don’t exactly reflect the reality of office attire. I often notice a common thread among young professionals, whether they’re entering their first internship or trudging throu…

Is Consumption-Core Catfishing You?

Stella Pyles — Fri, 04 Oct 2024 20:12:16 GMT

In your high-school yearbook, a superlative sits beneath your photo that reads, “Most Fashionable.” If five of your closest friends were asked to share one thing about you, they would unanimously agree that you’re a true fashion enthusiast. Your closet is a treasure trove filled with the latest pieces, tokens sourced from the likes of TikTok Shop, to th…

Are You Playing Seasonal Style Roulette?

Stella Pyles — Fri, 27 Sep 2024 20:57:50 GMT

As fall approaches, fashion publications relentlessly roll out trend forecasts declaring what’s in for the season, the colors that “everyone” is wearing, yadda yadda yadda. But what often goes unaddressed is how the shift of a season can evoke emotional responses that challenge our personal style, prompting a reassessment of what we wear and how it refl…