What does freedom look like when you navigate the world on wheels? For Jenna Udenberg, it arrived in the form of a Firefly - an electric attachment that transformed her manual wheelchair into an adventure vehicle capable of tackling trails she'd only viewed longingly from afar.

Diagnosed with juvenile rheumatoid arthritis at age seven and using a wheelchair by eight, Jenna refused to let her mobility challenges define her life's boundaries. From becoming a left-handed trumpet player (despite being told it wasn't possible) to creating adaptive music programs that helped non-verbal students find their voice, her journey exemplifies resilience and creative problem-solving.

The pandemic marked a turning point when Jenna left her 19-year teaching career and discovered a new calling as a disability advocate. Through her nonprofit "Above and Beyond With U," she champions the philosophy that true accessibility transcends mere ADA compliance checklists. As she powerfully states, "Nothing for us without us" - accessibility planning must include disabled voices from the very beginning.

Our conversation explores how Jenna discovered newfound independence on Minnesota's state park trails, the transformative power of community support, and why her autobiography is titled "Within My Spokes." You'll gain fresh perspective on what adventure truly means and how accessibility benefits everyone.

Whether you're disabled, know someone who is, or simply care about creating a more inclusive world, Jenna's insights will change how you think about accessibility in outdoor spaces. Listen now to hear more inspiring stories of people finding their own unique paths to adventure despite life's challenges.

Visit LandPirate.com to get your gear that has you, the adventurer, in mind. Use the code "Journey with Jake" to get an additional 15% off at check out.

Visit geneticinsights.co and use the code "DISCOVER25" to enjoy a sweet 25% off your first purchase.

#158 - What if your moments of greatest confusion were actually doorways to your most authentic self? Giovanna Silvestre's remarkable journey proves exactly that. From the high-pressure halls of Hollywood to the difficult decision of walking away from her family's beloved Italian restaurant, Giovanna's path shows how embracing uncertainty becomes your greatest strength.

With refreshing candor, Giovanna shares her descent into depression after attaching her self-worth to external validation—her Hollywood career, the family business, romantic relationships. The turning point? A disciplined approach to rebuilding herself from within through yoga, meditation, and gratitude practices that culminated in a profound spiritual awakening. "I woke up one day and literally felt like I was on Molly," she laughs, describing the natural high that forever shifted her baseline of inner peace.

The conversation takes us through her creation of the "Confused Girl in the City" blog, where weekly adventures from bungee jumping to flying trapeze taught her that confidence comes from stepping outside your comfort zone. We journey alongside Giovanna as she develops a crystal-inspired yoga clothing line that sells internationally, then follows her intuition to Bali and Berlin—spending two years abroad to write her new book "Confused Girl: Find Your Peace in the Chaos."

Giovanna's wisdom resonates deeply: "Confusion is the fuel for your self-discovery journey." Her story proves that when we remove the shame from not having all the answers, we open ourselves to living the life we truly desire. If you're feeling lost, uncertain, or simply curious about your next steps, this episode offers both comfort and practical guidance for transforming your confusion into clarity.

Ready to embrace your own journey? Pre-order Giovanna's book before May 13th at confusedgirlinthecity.com and enter to win a two-night oceanfront stay in Maui!

Visit LandPirate.com to get your gear that has you, the adventurer, in mind. Use the code "Journey with Jake" to get an additional 15% off at check out.

Visit geneticinsights.co and use the code "DISCOVER25" to enjoy a sweet 25% off your first purchase.

When David Schafran felt his life spiraling into depression and emptiness, he discovered an unexpected lifeline – salsa dancing. That first night on the dance floor sparked something profound: "It makes me feel so happy because it's so joyous and flavorful and juicy." This moment of clarity eventually led David from his high-stress tech startup in Boston to the vibrant streets of Medellín, Colombia, where he immersed himself in dance for five transformative months.

David's story challenges conventional thinking about wellness and healing. Despite practicing meditation and yoga, these solitary pursuits weren't enough to lift him from his emotional fog. What he desperately needed was connection, expression, and embodied joy – elements he found abundantly in the salsa dancing community. As he puts it, salsa offers three essential gifts: "joy, flavor, and affection."

This revelation didn't just change David's personal life – it birthed a mission. Through his company Soma Loco (meaning "we're crazy together"), he now creates personalized dance immersion experiences that help others discover the same transformative power of movement. Whether you're an experienced dancer or someone who believes they have "two left feet," David's approach proves that dance isn't about performance but feeling. The results speak for themselves, with participants describing the experience as genuinely life-changing.

Ready to discover how movement might transform your life? David's journey reminds us that sometimes healing isn't found in stillness, but in rhythm; not in isolation, but in connection. As he advocates, dance isn't just fun – it's medicine that should be taken seriously as a path to well-being. Follow your curiosity to somoloco.com or @dancesomoloco on Instagram to learn how you might find your own rhythm.

Want to be a guest on Journey with Jake? Send me a message on PodMatch, here: https://www.podmatch.com/hostdetailpreview/journeywithjake

Visit LandPirate.com to get your gear that has you, the adventurer, in mind. Use the code "Journey with Jake" to get an additional 15% off at check out.

Visit geneticinsights.co and use the code "DISCOVER25" to enjoy a sweet 25% off your first purchase.

Bonus 8 - Dr. Douglas Brouwer's journey from Western Michigan to the world and back again offers profound insights into how travel shapes our spiritual lives and understanding of home.

After spending 40 years serving as a Presbyterian pastor around the globe, Doug's adventures took him from maximum security prisons in Philadelphia to a church in Zurich, Switzerland, where he learned German at age 60. His travels weren't merely about seeing new places but about finding deeper meaning and connection with humanity.

The conversation explores Doug's most profound travel experiences, including walking 500 miles along the Camino de Santiago at retirement age. Despite averaging 17 miles daily for 28 days with everything on his back, it was the first night—stranded on a mountainside between France and Spain—that taught him the most powerful lesson about his own limitations. Yet he persevered, meeting fellow pilgrims from around the world who, regardless of religious affiliation, participated in the ancient spiritual rituals along the path.

What makes this episode particularly moving is Doug's reflection on the true purpose of all our wandering. After visiting 48 states and countless countries, writing a book called "The Traveler's Path," and experiencing diverse cultures, he found that his heart's true home was back near Lake Michigan where he began. "All of this moving around, all of the searching that people do, I think, is a search for home," he shares with emotion. "Where is it that I belong?"

Whether you're planning your next adventure or questioning the meaning of your travels, this conversation will challenge your perspective on what makes journeys worthwhile.

Visit LandPirate.com to get your gear that has you, the adventurer, in mind. Use the code "Journey with Jake" to get an additional 15% off at check out.

Visit geneticinsights.co and use the code "DISCOVER25" to enjoy a sweet 25% off your first purchase.

#156 - Chris Nance's life reads like an adventure novel where dropping out of school at 13 somehow leads to piloting massive ships down the Mississippi River and co-founding a successful coffee company. Growing up just south of New Orleans in a family of riverboat pilots and commercial fishermen, Chris's education took an unexpected turn after Hurricane Katrina when his mother discontinued homeschooling. Shortly after, his father was imprisoned for tax evasion, pushing Chris into the challenging world of commercial fishing before he could even drive.

The heart of Chris's early journey involves "koonin oysters" – a grueling harvesting method where he crawled through deep mud on hands and knees, using specialized tools to collect oysters from tidal flats. By day's end, he'd be pushing 1,500 pounds of oysters through mud. This backbreaking work built the foundation of grit and determination that would define his future success.

What makes Chris's story truly remarkable is his educational trajectory. Despite having only a GED and significant insecurities about his academic abilities, Chris was encouraged by mentors to pursue higher education. In a decisive moment aboard a tugboat, a captain convinced him he could succeed at Texas A&M Maritime Academy. Within days, Chris had relocated to Galveston and begun classes, ultimately completing his degree in just three years while taking up to 31 credit hours per semester.

Today, Chris navigates massive international vessels along the treacherous Mississippi River as a riverboat pilot and has co-founded Backbone Coffee Company with fellow outdoorsmen. The specialty coffee company roasts to order and aims to honor hardworking Americans building the country. For Chris, adventure must be both difficult and unknown – a philosophy that has guided his extraordinary journey from the muddy oyster beds to the helm of international shipping.

Ready to try premium coffee from someone who understands hard work? Visit backbonecoffee.com and use code JOURNEYWITHJAKE for 15% off your order.

Want to be a guest on Journey with Jake? Send me a message on PodMatch, here: https://www.podmatch.com/hostdetailpreview/journeywithjake

Visit LandPirate.com to get your gear that has you, the adventurer, in mind. Use the code "Journey with Jake" to get an additional 15% off at check out.

Visit geneticinsights.co and use the code "DISCOVER25" to enjoy a sweet 25% off your first purchase.

Most of us dream of adventures in far-off places, but between demanding jobs, packed schedules, and the sheer overwhelm of planning, those dreams often remain just that—dreams. Enter Ross Alcorn, the mastermind behind Itinerary Boss, who's made it his mission to turn travel aspirations into reality for busy professionals.

Ross's journey didn't begin with a goal to start a travel company. It started with a simple need—someone had to plan the group ski trips. As the designated planner among his friends, Ross developed frameworks for orchestrating everything from snowboarding weekends in Colorado to 17-day European adventures spanning multiple countries. These skills, honed over a decade while maintaining a demanding career in healthcare sales, became the foundation for his unique approach to travel planning.

What makes Ross's perspective particularly valuable is his firsthand experience with burnout. After a year with nine weddings and zero personal trips, he recognized a pattern affecting many high-achievers—the inability to prioritize adventure amid professional responsibilities. His response was to create systems that make meaningful travel accessible to those with limited time, teaching busy professionals to leverage credit card rewards, strategic booking windows, and streamlined planning processes.

The stories Ross shares—flying off a boat in Croatia, unexpectedly meeting the Croatian president, navigating Amsterdam's unique souvenirs through airport security—aren't just entertaining anecdotes. They're testament to how stepping outside comfort zones creates memories that far outlast any professional achievement or material purchase. His approach balances adventure with practicality, helping travelers bypass the overwhelm of endless research to focus on experiences that matter.

Ready to transform how you approach travel? Connect with Ross at itineraryboss.com, where you'll find his Stress Free Travel Starter Kit or tune into his podcast "World Travel Made Easy with Itinerary Boss" for weekly insights that make adventure accessible, regardless of how packed your calendar might be.

Want to be a guest on Journey with Jake? Send me a message on PodMatch, here: https://www.podmatch.com/hostdetailpreview/journeywithjake

Visit LandPirate.com to get your gear that has you, the adventurer, in mind. Use the code "Journey with Jake" to get an additional 15% off at check out.

Visit geneticinsights.co and use the code "DISCOVER25" to enjoy a sweet 25% off your first purchase.

#154 - Imagine plunging down a 35-foot waterfall strapped inside a kayak, or trying to compose a stunning piano piece that captures the serenity of nature. These are just fragments of Jon Cheney's extraordinary journey as a creator, adventurer, entrepreneur, and man of faith.

From his early years in a musical household where his parents prioritized owning a grand piano before even having proper furniture, to his teenage years in Paraguay learning Spanish, Jon's life has been defined by embracing new challenges. His remarkable ability to master languages – including Mandarin Chinese during his church mission – parallels his approach to music composition, where he sees patterns and structures that most miss.

The heart of our conversation explores Jon's passion for whitewater kayaking and the profound life lessons it's taught him. "You're going to flip over in life," Jon explains with the wisdom of someone who's faced Class 5 rapids and business setbacks alike. "But when you've learned that you can flip over and then get back up and be okay, then the world really opens up." This philosophy has guided him through entrepreneurial ventures, creative pursuits, and personal challenges.

What makes Jon's perspective particularly refreshing is his recent epiphany about pursuing multiple passions. After years of praying for divine guidance on which path to choose – music, adventure, business, or writing – he found peace in Elder Uchtdorf's simple wisdom: "It mattereth not, only be faithful." This liberating principle has energized Jon to embrace all facets of his creative spirit rather than waiting for permission to begin.

Whether you're considering your own adventure into whitewater kayaking, struggling to choose between multiple passions, or simply seeking inspiration from someone who's mastered the art of getting back up after life flips you over, Jon's story will leave you both entertained and equipped with a new perspective on life's rapids. Follow Jon on Instagram @cheneypiano or on his website joncheney.com to continue following his journey of creation and adventure!

Want to be a guest on Journey with Jake? Send me a message on PodMatch, here: https://www.podmatch.com/hostdetailpreview/journeywithjake

Visit LandPirate.com to get your gear that has you, the adventurer, in mind. Use the code "Journey with Jake" to get an additional 15% off at check out.

Visit geneticinsights.co and use the code "DISCOVER25" to enjoy a sweet 25% off your first purchase.

#153 - Meet Ryan Mellon, a man who completely transformed his life by breaking free from the grind of 80-hour workweeks to embrace a life of global adventure. For over a decade, Ryan worked grueling 14-hour days, splitting time between fixing deep fryers and sorting packages at UPS, until a transformative two-week trip to Costa Rica ignited a vision for something different.

This captivating conversation tracks Ryan's methodical journey from overworked employee to successful digital nomad coach. After convincing his friends to join a year-long RV adventure across America, Ryan discovered he could leverage his real estate license to earn remotely – the pivotal realization that launched his location-independent lifestyle. Seven years later, he's worked from 23 US states and 22 countries while developing multiple income streams.

Ryan breaks down the three primary paths to digital nomadism – remote employment, freelancing, and entrepreneurship – offering practical insights for anyone considering this increasingly accessible lifestyle. With 66 countries now offering digital nomad visas and co-living spaces emerging worldwide, the barriers to location-independence continue to fall.

The episode brims with riveting travel tales, from motorcycle journeys through rural Vietnamese mountains to living on catamarans in crystal-clear Bahamian waters. Ryan shares both the extraordinary benefits of digital nomad life and its genuine challenges, including navigating internet reliability and combating occasional loneliness.

Now operating as a "hybrid nomad," Ryan splits his time between summers on his Virginia sailboat and winters abroad, with Bali emerging as his absolute favorite destination. His coaching practice helps others create their own versions of freedom, whether that means full-time travel or simply more flexibility and autonomy in daily life.

Ready to reimagine what's possible in your work and life? This conversation might just be the permission slip you need to explore new horizons. What adventure awaits when you step beyond conventional boundaries?

To learn more about Ryan and his coaching be sure to check out his website thedigitalnomadcoach.com and you can also check out his Instagram account @thedigitalnomadcoach.

Want to be a guest on Journey with Jake? Send me a message on PodMatch, here: https://www.podmatch.com/hostdetailpreview/journeywithjake

Visit LandPirate.com to get your gear that has you, the adventurer, in mind. Use the code "Journey with Jake" to get an additional 15% off at check out.

Visit geneticinsights.co and use the code "DISCOVER25" to enjoy a sweet 25% off your first purchase.