Did You Keep Saying Yes? | Sara Roccisano on Transformational Travel, Trusting Your Intuition, and the Journey Back to Yourself

What happens when the life you've built no longer fits the person you're becoming?In this episode of The Story of Us, Jeff Ellison sits down with traveler, writer, entrepreneur, and founder of Embolden Adventures, Sara Roccisano, for a conversation about walking away from certainty, answering life's quieter invitations, and discovering that the greatest journey is often the one within.Sara's path has been anything but predictable. She built a successful career that included Wall Street , but beneath the achievement was a persistent call toward something more. Eventually, after reaching a breaking point in 2022, she stopped, let go, and began rebuilding her life around travel, writing, transformation, and adventure.Having traveled to more than 40 countries, Sara sees travel as far more than collecting passport stamps. She believes stepping into unfamiliar places builds courage, challenges assumptions, and reminds us that wherever we go, people are remarkably proud of their homes, cultures, and stories—and often eager to welcome us into them.Her adventures have included scuba diving, climbing Mount Fuji and Kilimanjaro, journeys through the Amazon, encounters with ancient spiritual traditions, and experiences with ayahuasca that became part of her forthcoming book and transformational work.But beneath all the adventure is a much more universal story:What do we do when we hear the call to change?Sara's answer is simple:Pick up the phone.She believes our calling has a way of finding us—and if we ignore it, it may keep ringing until it becomes impossible not to hear.In This EpisodeLeaving a successful career when the old life no longer fitsWhy preparation creates opportunities that look like luckTraveling to more than 40 countriesWhat adventure teaches us about courage and humanityClimbing Mount Fuji and KilimanjaroThe Amazon, ayahuasca, and spiritual explorationMoving from control toward surrenderWhy travel can become pilgrimage and transformationBuilding Embolden AdventuresSara's upcoming book and transformation seriesLearning to trust curiosity, intuition, and the next stepMemorable Quotes“Chance favors the prepared mind.”When Jeff asks what Sara would tell her five- or six-year-old self—the little girl fascinated by pyramids, maps, flags, nature, and faraway places—she answers:“You're beautiful. You're amazing, and it actually is going to come true. I promise you.”Her message to her future self is even more unexpected. Rather than giving future Sara advice, she realizes future Sara may be the one guiding her:“I think I need to listen instead of be the boss, because the future Sarah's the boss.”Maybe that's the invitation for all of us. Listen for the restlessness. Trust the curiosity.Take the next step before the entire path becomes visible.Because every passport stamp eventually fades and every destination becomes a memory.The person you become along the way—that's the real adventure.ConnectFollow Sara and learn more about Embolden AdventuresVisit TheStoryOfUsProject.com for more episodes and subscribe free to Letters from the Middle of It All, Jeff's weekly Thursday reflections If this episode reminds you of someone standing at the edge of a new chapter, share it with them.Sometimes the path appears only after we're brave enough to take the first step.