Episode 32 / Lindsey Epperly
Stepping Back to Move Forward: The Brave Decision to Leave My CEO Role
What You'll Learn in This Episode:
How to Listen to Your Inner Compass: Lindsey shares how she navigated the emotional and mental hurdles to know when it was time to step down as CEO and embrace a new chapter.
What it Means to Redefine Leadership: The episode highlights how leadership isn’t always about being the face of the company, but understanding when and how to evolve into a new role that serves both the business and yourself.
Tips for Navigating Career Transitions with Grace: Listeners will gain insight into the steps Lindsey took to make such a major decision—from prayer and reflection to facing fears of change—and how to apply these principles in their own career transitions.
About Lindsey
Lindsey Epperly is the founder and owner 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.
"Bravery doesn’t always look like pushing through or holding on. Sometimes, the bravest thing we can do is step back, to trust that the world will keep spinning even when we’re not the ones at the helm."
Lindsey Epperly
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Hey listeners, it's Lindsey, and I'm wrapping up this season with a solocast, as I tend to do, and it's significant for me because this is not just wrapping up a season of the show, I'm also in the process of closing a chapter and wrapping up a season of life and work in a way that I never imagined myself doing. To fill you in, one month ago, I stood in front of my team and announced something I never imagined I’d say out loud: I’m stepping back from the company I founded. It’s a decision that’s been slowly unfolding over the past few years, and I want to share a bit of that journey with you because it ties so closely to the idea of bravery—specifically, the bravery to let go.
Since making that announcement, the number one question I’ve been asked is: “How did you know it was time?”
I wish I had a simple answer for you. But the truth is, there wasn’t one clear moment or sign. It felt more like a slow dance, a series of steps that took place over the ten years I’ve been leading this company. For me, stepping back wasn’t a decision made overnight. It was a process—a thousand tiny nudges that finally led me to a point of clarity. And in the months leading up to this, it felt even harder. I truly love the company I’ve built, and making this move required a lot of work of putting my ego to the side and asking: what is best for this company? I refused to let my day-to-day involvement be the short term gain that deteriorates Jetset’s long term success.
But let me back up for a minute and share the personal moments that led me to this:
At the end of 2019, I suddenly and unexpectedly lost one of my best friends, Joo-Ri. Her family gave me the greatest honor in the world of writing her obituary. I’ve always been a writer, appreciated that her family recognized I’d be the person for that job, but something in me clicked as I wrote the words about a life cut too short. As I was writing the words that would honor my friend, I made a promise to myself that I would not take my life for granted.
Little did I know at the time that I was pregnant with my first daughter. We entered into a season of excitement, paired with a season of uncertainty as the pandemic hit and we were forced to walk away from everything - our home, our community, all of it to keep our business afloat and give my daughter a chance of the future we’d been dreaming of as entrepreneurs. Becoming a mother gave me a new lens on everything. When I had Mila, I remember the fear and uncertainty that came with her difficult delivery and the hospital stay that followed. The whole experience brought this incredible clarity about what truly mattered, and eradicated me of the anxiety over the things that didn’t. I’d been so caught up in constantly people-pleasing to the point where I lived my life living up to the expectations I thought others had of me, instead of asking what expectation I had of myself. And all the while, behind the scenes, I was writing, writing, writing — from the minute I wrote Joo-Ri’s obituary just eight months before, I never. Stopped. Writing.
But business began to return to normal and opportunities arose, incredible ones, like the ability to acquire another company I’d long since admired. And because it was what the company needed of me, I stepped into the role of CEO. I studied up on what it meant to be a great one, squared my shoulders, and attempted to become the type of leader I always wished I’d encountered, and to build the kind of business I always wanted to work for. Personally, I had a goal of landing on the cover of Luxury Travel Advisor Magazine and doubling the modest size of the agency I founded by the time I was 40; because of the opportunities we seized in the pandemic, I was able to achieve that goal by 32. Those achievements were incredible, but they were a false summit, just like Jess Ekstrom talked about in our interview a few months ago, I’ll link to that in the show notes. I'd been chasing a dangling carrot of someone else’s definition of success.
Then, as I was attempted to lead two companies and power through the continued spiral of the pandemic, still making enormouse sacrifices in our personal life to ensure the success of the business, I was sitting at the kitchen table, talking to my husband, and I fell over into a seizure. This completely unexpected medical event sent me into such a dark time of uncertainty, one where I had to follow the trails of a misdiagnosis and eventually learn to find hope in spite of the outcome. During that time, I was faced with the fragility of life in a way I’d never experienced, and I remembered the promise I made to myself after my own friend’s life cut too short. The seizure was another wake-up call.
When the seizue happened, I was tempted to fold into myself, to live small. I’ll never forget attending an industry conference for the first time after, I walked around terrified that I’d collapse out of nowhere. I still couldn’t drive, couldn’t even take a bath by myself, how in the world was I expected to lead a company? So I relied on my partner, my husband, and the team we were building. This taught me something huge: bravery doesn’t always look like pushing through or holding on. Sometimes, the bravest thing we can do is step back, to trust that the world will keep spinning even when we’re not the ones at the helm.
All of those experiences were the little moments that gave me clarity around how my company, my role, and I myself were evolving, eventually leading to the decision that it was time to let go of the CEO role. I’d stretched myself to fill the role the business needed me to play. But the truth? I never set out to be a CEO. I set out to build something meaningful—something that helped others believe in their value, even when I wasn’t so sure of my own.
I started Jetset World Travel from a place of brokenness. I was 25, sitting on the floor of my bathroom, feeling the weight of a toxic relationship, convinced I had nothing left to offer the world. But there was this little voice, a spark of hope inside me, that said, “You can create something that matters.” And I did. I built a company that’s had an impact on so many lives, not just mine.
But now, my purpose has evolved, and I’ve come to realize that my role needs to evolve with it, and what Jetset needed ten years ago when I founded it looks so different than what it needs today, and it’s the honor of a lifetime to be able to make a decision to let my baby spread its wings without its founder hovering over its shoulder. The decision doesn’t diminish my love for what I’ve built - in fact, it reinstates it. I spent a week in Ft. Worth with our team and was reminded of all the wonderful humans that have been drawn to this company, and how much we’ll be able to serve them and future individuals because of this decision. I want Jetset to be around for decades beyond this first one, and propping it up to be a success without its relying on me is an essential piece of that puzzle.
Not to mention, Jeremy is stepping into the CEO role, and I couldn’t be prouder of him. He was made for this. Where I shoot first and aim second, Jeremy is playing chess - a strategy guy who can look at the market years beyond where we are now, and a man of character that I get to see behind the scenes as he dances with his daughters and serves his family and friends from a place of showing up, and of integrity. And as for me, I’ll be serving in an advisory capacity—a position that feels right for where I am and where I want to go next.
So, how do you know when it’s time to step back? When it’s time to take that brave leap?
The answer may not come all at once. Sometimes, it’s about trusting the process, following the small, quiet nudges over time, and having the courage to admit when you’ve reached the end of a chapter.
Right before I made my announcement to the team, I prayed. I stood in the bathroom and asked God, “What do you want me to know here?” And in that quiet moment, I felt a sense of peace wash over me, I heard, as clearly as I could, the words of a verse on my heart. Well done, good and faithful servant. It was my confirmation that it was okay to let go.
I want to turn this back to you. What’s the bravest thing you’ve ever done? Maybe you haven’t figured that out yet, or maybe you’re living in the middle of it right now. For me, the bravest things I’ve done have always involved leaving. I left a toxic relationship. I left my hometown, searching for a place where my heart felt at home. I left a safety net to start Jetset. And now, I’m leaving the CEO role because I know it’s what’s best for the company and for me.
Leaving doesn’t always mean giving up. Sometimes, it’s the bravest form of growth. It’s expanding so that others can step into their own purpose. Like Shannon Miles reminded me recently during our conversation—there’s a Law of Expansion: we expand, we gain power, and then we give that power away for the sake of others. And then we repeat.
That’s the season I’m in now. I’ve expanded. I’ve gained power through the work I’ve done. Now, I’m giving that power away, trusting that it’s time for someone else to take the reins. And that’s okay.
So, I’ll leave you with this: where in your life are you being called to expand? What brave step do you need to take, even if it feels scary, even if it feels impossible?
Maybe it’s stepping back. Maybe it’s stepping into something new. Maybe it’s that you know your purpose, but you haven’t leaned in to the point where it’s a priority. Whatever it is, I hope you listen to that quiet voice inside and trust that you were made for more. You were made to expand, to give your power away, and to create space for others to do the same.
Thank you for being part of this journey with me. I can’t wait to share what’s next, and I hope you continue to follow your own path with bravery and purpose. Stay tuned for Season 4 in early 2025, but in the meantime, let’s stay connected. Join me on Substack at lindseyepperly.substack.com for more reflections on purpose, bravery, and the beautiful mess of figuring it all out.