Episode 2 Solocast / Lindsey Epperly
Adversities, Growth, and The Monsters That Save Us: What You'll Hear About On Who Made You The Boss?
What You'll Learn in This Episode:
Lindsey details her entrepreneurial evolution, providing insights into the challenges and successes behind Jetset World Travel.
The reality behind the less glamorous side of leadership, acknowledging the struggles faced by leaders, whether in their own businesses or within corporate structures.
The commonality of modern professional challenges, like imposter syndrome and burnout, and how these span across industries.
The concept “the monsters that save us”: exploring events that compel individuals to release control and follow the four R's: reactions, reasons to change, retraining past behavior, and redemption.
Lindsey’s personal story of turning failure into success and how she went from walking away from her home to landing on the Inc. 5000 list in less than three years
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.
In this solocast episode, we're introduced to our host, Lindsey Epperly, as she shares more about what listeners can expect when tuning into Who Made You The Boss? We'll dive into the challenges today's modern professionals face in a safe and inclusive community. Listen as Lindsey underscores the importance of overcoming adversity for growth, citing her company's success post-departure of the first hire and navigating the industry's greatest crisis to eventually quadruple in growth and land on the Forbes Next 1000 and Inc 5000 lists. Throughout the season, Lindsey promises to share personal triumphs and interview inspiring guests, collectively addressing the question of, "Who made you the boss?" and encouraging listeners to take the reins of their personal and professional journeys.
“We didn't become bosses to wear a crown; we did it because we believed we could make a difference in the world, even in moments of self-doubt and adversity. These conversations and this community will empower us to confront our monsters and fears together. It's time we embrace our stories and share the authentic versions of our leadership journeys.”
Lindsey Epperly
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Hey there, friends. I'm Lindsey Epperly, and I'm here to take you on a journey through the highs and lows that the modern professional faces in today’s world. Before we dive into the interviews, let me give you a little background on who I am. My professional path has been forged mostly within the hospitality world, ever since founding what is now Jetset World Travel, where I sit as the CEO. But my entrepreneurial spirit dates back to the age of four when I sold imaginary ice cream to my dad. My real journey began at nineteen when I started building a personal book of business as a travel agent. Fast forward to 2014, and I launched my own travel agency, growing from a solopreneur to an entrepreneur.
I'm deeply passionate about business - in fact, my current company isn't just about raising experts in our industry; it's about nurturing entrepreneurs who can innovate and make a lasting impact. I believe in the power we all have to turn our wildest dreams into reality. Whether we identify as a boss, per se, we all can identify as leaders. Some of us lead at the office, some at home, but all of us are leading ourselves to becoming better people, to pursuing fulfillment without sacrificing ourselves, and that makes us all leaders in some way, shape or form.
But let's be real. Being a leader isn't all glitz and glory as our culture often portrays. We've glamorized leadership to the point where the sizzle is all that outsiders see. But for those of us in the trenches, we know it comes with its fair share of struggles, whether you're running your own company or leading within someone else's.
I've always been a bit bossy, and that hasn't changed. When I was a little girl, I remember vividly when I would go into control mode and my very sassy Nana would ask, "And who made you the boss?” Now, decades later, I find myself asking that same question regularly. Imposter syndrome has been a constant companion on my professional journey. And I'm sure it manifests differently for each of us, whether we’re self employed or working in the corporate world, this ringing question of “why am I in charge here?” can be a breeding ground for insecurity. We’ll be having a lot of conversations around the value we have as humans, which is something I believe in so strongly that it’s one of my company’s core beliefs: we believe in the value we add.
Speaking of beliefs, I make no attempt to hide my own beliefs as what guide me through my professional endeavors, but this podcast and community are being intentionally curated as a safe and inclusive place, regardless of your beliefs or background, skin color or gender, you are welcome here.
My personal beliefs are informed from my own faith, which is really something that has evolved for me over the years since I first attended Christian School. Christian school, I can now lovingly say, was kind of hysterical. The phrase “Christian school education” is a bit oxymoronic, considering how much information is left to unearth outside of the campus, like the scientific discovery of the Homo Erectus, or the entire concept of sex-ed, or that Disney movies are not actually filled with devil worship. Guys, I still get anxious when I hear Phil Collin’s soundtrack from the movie Tarzan - and it’s not because he is lighting the piano on fire with his talent, it’s because I was once told that was devil music.
That’s neither here nor there, you won’t be getting anything evangelical here - I’ve had my own sorting to do with that misinformation. What I do want to share today is a story I first learned at Christian School - maybe you’re familiar with it, the story of Jonah and the Whale. I’ve so often felt like Jonah’s journey paralleled my own path. See, Jonah was called to a specific place for a specific purpose, but instead of marching confidently toward that path, he tried to run away from his destiny. But God had other plans. In the midst of a terrifying storm, Jonah found himself in the belly of a gigantic whale, which eventually led him back to the purpose he was made for. Within that unwanted destination, he delivered a message only he could. Jonah made an impact because of the very thing that saved him—the monster that swallowed him whole.
And that's a question I'll be asking the remarkable guests I interview on this podcast: what are the monsters that have saved you? Where did you think you'd lose it all, only to regain it tenfold? As I've learned, the events we fear the most are usually what make us into who we’re supposed to be — and that’s because the events we fear the most are rooted in our deep need for control.
From my experience, the way we loosen our death grip on control follows the same pattern: four R’s. We are rooted in the first R: reactions, typically the bad habits we have that we’ve fallen into like a well-worn groove, from our perfectionism to our fierce dedication against accepting help. This is all fine and dandy but slowly crushing us until the inciting event, the second R: we are given a reason to change. These are oftentimes external circumstances — our monsters, if you will. Perhaps your monsters look like the glistening edge of a spear that has pierced through your veil of success. Maybe the monsters are the empty space at the table after the sudden loss of a loved one. They could even be that millisecond in time between the moment when you are upright at the kitchen table, speaking coherently to your husband, and the next minute when you are unconsciously seizing on the floor, and now you have a new chapter with an uncertain diagnosis looming overhead.
For me, it was all of those things. Each monster was a turning point, a reason to shed some layer of control I thought I had, to break down the boundaries that kept me from listening to my intuition. This is what allows us to encounter the third R: the opportunity to retrain our past behavior. A good example of this is my own fierce independence: it’s something I love about myself, actually. I mean, my mother had to read the Strong Willed Child…twice. I’ve always worn this refusal to accept help as a badge of honor, if anyone is getting us to our next phase, it’s me. But my big reason for changing this bad habit is first because of what happened to my company: there are not enough words to describe what it’s like to run a travel agency during a world pandemic. Every day I would wake and think what fresh new hell awaits? We had to rescue people from Argentina as boarders were closing, we had to cancel trips that were people’s last opportunities to spend with relatives who may not be there once the world reopened. And my team, God, my team was so incredibly strong, but it was wrecking all of us - and each day we get to do it all over again for negative income.
Add to this the fact that I was 5 months pregnant when the pandemic hit and had just placed a home under contract. My husband was not my business partner at the time, but he was working in the company, so we’re a single income household really banking on our dreams that this business is going to take off - and it plummets. Every day, we’re bleeding money. Every day, we’re opening up a spreadsheet we’ve labeled Project Slim Fast and going…we can make it this many more months. We had to ask ourselves: do we keep our business, or do we keep our home?
So we walked away from the home, uncertain of where we’d be bringing our firstborn home to, and we started taking about what this business would look like if it survived. Jeremy offered true partnership - he would come in and help me run the business, he had ideas about how we could scale it, he had a lot of things that sounded to me, quite frankly, threatening to the way I’d always ran my business and my life - completely within my control.
Now, this reason was my opportunity to retrain my bad behavior of wanting to do everything myself. It didn’t come that easy, of course - the monster that was this leveling of my business had to completely destroy my sense of self worth because it was so wrapped up in my success - but once that was done, once I accepted the failure that seemed inevitable, when I had nothing left to lose, only then did I accept the help of a partner.
And you know what, guys? That’s what led to the 4th R: redemption. Embracing the opportunity to change opened the bottleneck I had on my business and it began to flourish. The funds we were supposed to use toward a home? What was left of them after keeping the business alive were put toward an acquisition opportunity, that’s how we bought Jetset in 2021. The monster that was failure led to a quadrupling of growth that the company has experienced since March of 2020. That monster landed us on the Inc 5000 list of the fastest growing privately held companies in 2023.
And that’s just one redemption story I can and will share with you personally, including a future conversation on how escaping a private island allowed me to tackle imposter syndrome, and those are only my stories — you’re going to hear so many more incredible conversations of turning tragedy into triumph thanks to our incredible guests. Together, we'll wrestle with the question posed by this podcast's name: Who made you the boss?
I'm ready to tackle that question with you. We didn't become bosses to wear a crown; we did it because we believed we could make a difference in the world, even in moments of self-doubt and adversity. These conversations and this community will empower us to confront our monsters and fears together. It's time we embrace our stories and share the authentic versions of our leadership journeys.
Thanks for joining me today. Stay tuned for more inspiring episodes, as we dig deep into the world of leadership and ask ourselves, "Who made you the boss?"