Kristen Van Nest: The Transformative Power of Travel
Kristen Van Nest - photo credit Kristen Van Nest
Ep 168 - Kristen Van Nest: The Transformative Power of Travel On Her Latest Book - 'Where To Nest'
My 168th guest episode on the Winging It Travel Podcast is with Kristen Van Nest, a comedian, author and adventure traveller.
Welcome back to the Winging It Travel Podcast, where we celebrate the magic and chaos of travel!
This week, I welcome Kristen, whose book Where to Nest: A Global Search for Love, Cheap Wine, and a Place to Belong, chronicles her hilarious and heartfelt journey as a millennial navigating cultural quirks, relationship missteps, and personal growth.
This ia an episode packed with unforgettable anecdotes, including her take on how travel has evolved for millennials, the comedic lessons she’s learned from globetrotting, and a ski date in Switzerland that turned into a literal downhill disaster.
Whether you’re a backpacker, a digital nomad, or simply a curious soul who loves a good travel story, this episode is full of laughs, insights, and inspiration.
Let’s dive into some topics.
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The Millennial Travel Shift: From Napster to Google Maps
Kristen dives into how travel has dramatically transformed for millennials, a generation that straddled two very different eras of exploration. She reflects on her teenage years, navigating cities armed only with paper maps and handwritten directions, compared to today’s hyper-connected, app-driven world.
Millennials are uniquely positioned, having witnessed the birth of the internet and social media while still remembering what it was like to rely on word of mouth and old-school travel guides.
Kristen shares her mixed feelings about this shift. While tools like Instagram and Google Maps make planning easier, they can sometimes rob travelers of spontaneity and local authenticity.
For Kristen, travel is about immersing herself in the rhythm of a place—wandering through neighborhoods, stumbling upon hidden gems, and connecting with locals, rather than chasing viral Instagram spots.
She humorously admits to once meticulously planning a trip using social media, only to end up exhausted and longing for the freedom of her old-school travel days.
If you’re wondering how to strike a balance between convenience and discovery, Kristen offers valuable tips, like focusing on neighborhoods instead of rigid itineraries and embracing the occasional "no-plan" days.
Kristen’s Journey into Comedy
How does a globetrotting millennial turn her adventures into stand-up gold?
Kristen shares the winding path that led her to comedy, beginning with her upbringing in a conservative East Coast town and later moving to Los Angeles.
She talks about how her international experiences shaped her comedic voice, providing her with endless material rooted in the absurdities of travel, culture shock, and navigating adulthood.
Kristen opens up about the challenges of carving out a career in comedy while balancing freelance copywriting work and her love for travel. Her story illustrates how passion and persistence can turn life’s messiest moments into creative fuel.
For example, she recalls using her improvisation skills to navigate language barriers abroad, turning miscommunications into hilarious stories that later made it into her stand-up routines.
Whether she’s poking fun at her near-miss misadventures or examining the millennial struggle to find meaning in a chaotic world, Kristen’s approach to comedy is as relatable as it is laugh-out-loud funny.
Her story is a testament to the power of humor to connect people across cultures and experiences.
A Near-Death Skiing Incident on a Date
It’s one thing to impress a date with a cool adventure; it’s another to risk life and limb in the process.
Kristen recounts the time she visited Switzerland to meet a romantic interest who suggested an “off-piste” skiing route.
Fueled by attraction (and perhaps a touch of peer pressure), she agreed, only to find herself staring down a 45-degree slope that was far beyond her skill level.
What followed was a mix of panic, adrenaline, and a reality check.
While her date confidently skied down the treacherous trail, Kristen froze in terror, realizing there was no turning back. With cliffs on either side and no safety nets, she opted for the least glamorous—and safest—option: rolling down the hill like a human snowball.
Her date, unfazed, offered the unhelpful advice of “You’ll learn by falling,” which Kristen sarcastically dubbed the world’s worst pep talk.
After surviving the ordeal, she was less enamored with her date and more appreciative of her own survival instincts. This hilarious yet harrowing tale serves as a reminder to never overestimate your abilities—or underestimate the risks of mixing adrenaline sports with romance.
Kristen's book cover - Where To Nest
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Who is Kristen Van Nest?
Kristen Van Nest is the author of "Where to Nest: A Global Search for Love, Cheap Wine, and a Place to Belong"—a memoir that Arab News calls a "funnier, more relatable millennial version of 'Eat, Pray, Love'."
Kristen's journey spans over 40 countries, and her book blends humour with insights on travel misadventures, dating dramas, and finding belonging as a young professional abroad. Kristen is also an observational comedian and this episode has plenty of laughs making it a perfect fit for the Winging It Travel Podcast audience.
Kristen Van Nest’s episode is packed with humour, insights, and unforgettable anecdotes that remind us why we travel: for the stories, the growth, and sometimes the absurd moments that make us laugh for years to come.
Her book Where to Nestis a must-read for anyone who’s ever felt like a fish out of water while chasing adventure, love, or just a cheap glass of wine.
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