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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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Episode Highlights
Stephanie shares how family vacations to Disney sparked her early love for travel and curiosity about the world.
She explains how formative middle and high school trips inspired her to create unique, personalized travel experiences through her company, Lost in Adventure Travel.
The conversation explores how travel builds empathy and human connection by meeting people, hearing their stories, and seeing everyday life in different cultures.
Stephanie discusses how being a parent influences her approach to accessible trip planning, focusing on visual schedules, pacing, and flexibility so every traveler can fully participate.
Both reflect on the importance of downtime and moments of rest during travel, recognizing that learning and reflection often happen in those quiet spaces.
She talks about concerts and live music as experiences that bring people together, reminding us of our shared humanity.
Featured Quotes
Why travel matters
We as humans have a tendency to live inside our own echo chambers, and when we push ourselves beyond our comfort zone, which travel really can do, whether it's stepping on the airplane, getting on the train, just leaving our homes sometimes can be scary. It challenges our mindset, it challenges our bodies physically sometimes, it expands our worldview, it allows us to meet people that aren't just like us....it's really important to try and understand where other people are coming from, mindsets, like, physically, where do people live? How is it different than what my house looks like? How is it different than how I was raised?
Power of a Guide
....guides are the storytellers of the destination. Guides, I think, make or break a vacation
Creating Wanderlust Locally
Allowing yourself to go out and try a new restaurant. Try, like, go for a hike in a place you've never been. Those kind of experiences help drive the wanderlust as well, and allow us to step outside of that comfort zone a little bit.
Challenge for Living
..don't be afraid to take that first step. Whether you are traveling to Asia, or you're exploring your town, going to the concert that you wanted to go to, allow yourself to have the human experiences.
Challenge for Immersion
...allow someone to tell you a story about where you live about the town next door, go to a museum. Allow yourself to take the tour. Don't… just be your introverted self. Don't just grab your phone and learn about it, but go out there and talk to these people. And, I just think that overall, we will be better off.
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Suggested Past Episodes
215: Born to Jump — Tara Martin on Courage, Story, and Self-Care
Why it fits: Courage and story as catalysts for change which are the same muscles you need to launch travel experiences or classroom micro-adventures.
214: From Independence Day to Interdependence — Steven Puri
Why it fits: Designing work that prioritizes culture, presence, and curiosity is perfect framing for travel as community-building.
104: Estella Owoimaha-Church — Building Empathy through the Arts
Why it fits: A deep dive on empathy and restorative practices; complements this episode’s theme of travel as perspective-taking.
227 episodes
