Episode 12 / Lindsey Epperly
I Don’t Fit In, Now What? Celebrating Uniqueness To Cure Imposter Syndrome
This episode is for you if you’ve ever wondered:
What is imposter syndrome?
Can I use my obstacles and insecurities to help me grow?
Does our non-professional past impact our professional growth?
Why is it important to study the origin of our imposter syndrome?
About Lindsey
Lindsey Epperly is the founder and CEO of Jetset World Travel, a modern travel agency dedicated to service, innovation and gratitude. Lindsey’s decade-long journey in the world of business started as a one-person operation built by attending bridal shows alongside her college courses that she and her business partner have transformed into a company of 70 mission-driven team members. Lindsey’s passion for entrepreneurship, as well as her outspokenness on battling burnout and imposter syndrome, have led her to earning a spot on the 2021 Forbes Next 1000, along with speaking and writing opportunities about turning obstacles into opportunities. She is currently studying under New York Times bestselling author Bob Goff to produce a book about the illusion of control.
“I could not control whether I came from the right pedigree, but I could control whether or not I succeeded. And I was determined to succeed brilliantly. So in so many ways, I believe our rumblings with insecurities can actually become rocket fuel toward our dreams.”
Lindsey Epperly
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Lindsey Epperly [00:00:02]:
Welcome, friends, to another season. Season two of who made you the boss? So, based on the overwhelming response I received to our season finale about turning imposter syndrome into inspiration, you will see a concerted effort in this season to really drill down on the topic of imposter syndrome. Right. What is the definition of imposter syndrome? How do we go about tackling this? I've even created a workbook for you. It's a free resource on the website lindseyperleigh.com resources. And I've got a lot of prompts that actually helped me after I had that insane battle with imposter syndrome and had to flee the private island retreat. If you haven't heard that full story yet, it's episode eleven from season one, and I will link to it in the show notes. Today, though, I want to rewind to the origin story of my own imposter syndrome.
Lindsey Epperly [00:00:49]:
There are actually a couple of milestones in this. I think it's important that we think back to the ways in which these types of things first manifested in ourselves. And because really studying the emotions is actually part of the process. It's one of the things I even note in the workbook. Um, my own experience career wise, this little Gremlin started when I first began in my profession. So before I owned Jetset World Travel and sat as the CEO, which has brought its own slew of imposter syndrome moments. I mean, why do you think I created this podcast? I spent my twenties as a luxury travel advisor. So what does that actually even mean? Well, I planned four and five star trips for clients looking to go around the globe, and that meant I got access to testing out the products.
Lindsey Epperly [00:01:30]:
And that is awesome, right? I mean, no one's going to argue that getting to spend your college spring break at the St. Regis Bora Bora is not a significant job perk. It is a significant job perk. But what if you're not all that accustomed to staying at a place of that caliber that is like a haven for celebrities. When I got there, Nicole Kidman had just left and they had recently filmed couples retreat. I mean, I was barely old enough to drink. And when that happens and you're so new and so fresh to things and your work takes you to a place like this, your brain can go one of two ways. Like one.
Lindsey Epperly [00:02:03]:
Wow. What an incredible perk that maybe I deserve for working hard. Or two. Oh, my God. How long before someone finds out that I am just a 20 year old who stumbled into a travel agency for a brochure and I accidentally walked out with a job. I mean, can the other patrons of this hotel tell that the nightly rate here is more than my entire apartment, probably yearly rent? Or that I've actually never stayed in anything nicer than a sheraton? I mean, will they find out? Will they know? Can they tell that I just don't truly belong here? It was on that same trip I had my first seven course tasting menu, which was an amazing experience. And I'm learning all these new things, but so intimidating, right? Like, what the heck is foie gras? And then also, which fork do I use for said foie gras, which caused a minor panic attack? I mean, I still don't know. I still don't know which fork you used that.
Lindsey Epperly [00:02:51]:
I think that in this industry, there are a couple different types of individuals, and there are some that feel like they naturally belong because it is actually the caliber of wealth and the lifestyle that they are accustomed to that they grew up with. And there's nothing wrong with that. That is amazing if you have that kind of background and access. But for those of us who did not, sometimes it feels like we're just waiting to be found out. So this theme would be reoccurring for me. And try as I might, I always felt like I was just off base from the expectations of what someone in this field should dress like or act like or talk like. Even now, even doing this podcast. Right.
Lindsey Epperly [00:03:28]:
Um, I tried so hard. I tried taking wine classes. I had, like, a private meeting with sommeliers to try to become more proficient in the bottles that I was being served at these work trips. And. And I even did an online etiquette course to try to learn about right cutlery to use when. And for some reason, it's like my brain is just not wired to retain this information. Like, I really, truly studied. And, you know, just like when I really, truly studied in my college business classes, I also really, truly feel there was even a moment when I was at a very nice luncheon upper echelon event in our industry, and one of the c suite executives saw my dress and commented, your dress is exquisite.
Lindsey Epperly [00:04:05]:
Is that vintage Chanel? And I said, oh, my God, no, it's banana. I was so proud it was banana republic. I'm still proud of it. But for the love of God, I could not just learn to smile and, like, pretend as though I'm wearing vintage Chanel. Guys. Try as I might, I just could not contort who I was and who I am at my core to the role that I was expected to assume in this world of luxury, I was a really good salesperson. I think I'm a really good leader. But that doesn't mean I have to be a really inauthentic version of myself to pretend that I'm someone I'm not.
Lindsey Epperly [00:04:36]:
And that is something I've really had to come to terms with as I continue to succeed in a world where I oftentimes feel like I don't totally belong. And a lot of this really didn't start on the job, even though, of course, the nature of a luxury industry doesn't do much to help it. The roots of this, for me when we talk about the origin story, actually trace back to high school. See, I attended a college prep school that placed more emphasis on whose name was on the building than anything else. No amount of kindness or character or even intelligence would supersede who you were based on your family worth. And my family did not have that. I mean, I was very lucky and very fortunate to go to that school. But during this tenure, I had a bit of an experience.
Lindsey Epperly [00:05:20]:
I dated a guy whose mother was just obsessed with climbing the ranks of social status. It was so obvious. But when he started dating me, he was going in the opposite direction of her dreams. So while my family did well for themselves, we just did not have the pedigree right. We did not travel to the St. Regis Bora Bora. We do not know. We still don't know which forks to use when.
Lindsey Epperly [00:05:39]:
And listen, I realize this is not a sob story. I come from a great amount of privilege, thanks to a family who worked really, really hard and showed up with incredible love. I was given amazing opportunities, thanks to a career path I never could have dreamed of. And I've hustled to turn even, like, a modicum of opportunity into abundance. But in this scenario, what I want us to focus on is that no matter what world or background or society or culture we are representing, it's never okay to intentionally make feel someone else like they don't belong. Like there is something inherently not worthy and who they are. As humans. I am so passionate about this that one of my company core values is, we believe in the value we add.
Lindsey Epperly [00:06:18]:
Because you are worthy, you have value. Don't ever let someone else other you. And I will never forget the way that this woman treated me. It was like I was a second class citizen. Her distaste was just obvious. But there was this one defining moment. The guy got invited to a debutante ball, which I didn't even know what that was. I still don't really know.
Lindsey Epperly [00:06:38]:
And I saw the invitation sitting on her kitchen table. I was visiting for a day, and there was an RSVP card at the top of that stack with his name on it. And there was an option, it was, of course, in her handwriting. And there was an option to check whether he would be bringing a date or going stag. And he was, of course, checked. Is going stag. I can't tell you the impact seeing one check mark made, but I, in that moment, felt like, gosh, even though I'm his girlfriend, I'm not good enough to accompany him to this social event. That my presence would have been a hindrance from him probably meeting the type of woman he should have been with, or worse, that I would have been an embarrassment.
Lindsey Epperly [00:07:22]:
Even though he had chosen me, the world where he belonged would never choose me. And I would always be an outsider, just an imposter trying to fit in. And I would imagine that this message sent a not so subtle reminder to my brain that when I attempt to enter into a room that is clearly made of a different societal status, I'm not good enough to actually belong. That's the reverberating echo that happened years later as I broke into an industry that, gosh, operated on an entirely different orbit than even my high school trip. I mean, I was brokering around the world private jet trips, which, like, why should I have a right to do that? That was a different caliber than even that high school came from. Right? But that's the thing. I use that imposter syndrome to my advantage. The way I was treated during my high school years became the chip on my shoulder.
Lindsey Epperly [00:08:09]:
I could not control whether I came from the right pedigree, but I could control whether or not I succeeded. And I was determined to succeed brilliantly. So in so many ways, I believe our rumblings with insecurities can actually become rocket fuel toward our dreams. Now, the dark side of that is, of course, left unchecked. It can become a bit unhealthy. But that's a conversation for another day. It is just so important we do the work to release ourselves of the misconception that finding our way is the same as fitting in, because it's not. I still don't entirely feel like I belong at these events or planning these around the world trips, but I know because of my faith, because of the work that I've done, that none of this is a reflection of my actual self worth.
Lindsey Epperly [00:08:53]:
And it shouldn't be for you either. So I'm just curious. This is how I'm putting myself out there. I'm curious if you felt this way too. I would love to hear from you as you do the work. If you're downloading the workbook again, that's at lindseyupperly.com resources that kind of helps you turn imposter syndrome into inspiration or just along the way, things that you you've learned. I plan on being right there alongside you, bringing you stories from some of the coolest leaders and entrepreneurs and creatives during this upcoming season. And I really want to hear from you.
Lindsey Epperly [00:09:22]:
When I started this podcast so I could feel less alone in my own journey and put things out there like this conversation today, it's super vulnerable. It just means the world to me when you respond to the newsletter or you send me a DM. So if we haven't connected, please feel free to reach out to me with or about what you want to hear on the podcast or tips and tricks that you've used along the way, or just if you've ever felt this in any capacity. If you think it would resonate with someone you know, feel free to share it with them now. That also means the world to me to know that my story and this work could help someone else. So thank you guys for being part of this journey. I am excited for another awesome season with you along for the ride.