There’s a moment many of us hit somewhere along the way, when we look up from our carefully planned lives and think, Wait… is this it?
My guest this week, Jen Ruiz, didn’t overthink that question—she acted on it. At the time, she was a full-time attorney with all the boxes checked: law school, bar exam, a clear career path. And yet, as she approached 30, something felt off.
“I couldn’t really think of a moment where I had taken time for myself… to just celebrate, to have fun.”
So she made a decision that would quietly—but completely—change everything. She committed to taking 12 trips in 12 months. Nothing extravagant, nothing perfectly planned—just a decision to go.
By the end of that year, those 12 trips had turned into 20, spanning 41 cities across 11 countries—and the beginning of an entirely new career as a travel writer.
🎧 Click on the above audio link to listen to our podcast interview on Substack, or find and listen to “The Gomes Guide Travel Podcast” on Apple Podcasts, Spotify, or wherever you listen to podcasts.
🌍 From One Trip to Something Bigger
What I loved most about Jen’s story is how simple it started—and how quickly it expanded.
We tend to think of travel as something big and aspirational. The two-week Europe trip. The bucket list safari. The kind of trip you plan for months (or years).
But Jen reframed it in a way that felt refreshingly doable:
“A trip could be a day trip… you don’t have to go far to have a new experience.”
That stuck with me.
Because the barrier to travel isn’t always money or time—it’s mindset. And sometimes the most meaningful trips are the ones that are close, easy, and a little spontaneous.
That same mindset is what shaped her career, too.
Jen didn’t set out to become a travel writer. She started blogging as a creative outlet while waiting for bar clearance, then began contributing articles. An editor discovered her work—and from there, things started to snowball.
Today, she’s a bestselling author, TEDx speaker, and award-winning journalist. But what really stood out to me is how intentional she’s been about building a real business around her work.
“The center is my travel expertise… and the spokes are all the ways I share it.”
Her work spans:
Writing for publications
Speaking
Brand partnerships
Media appearances
It’s a reminder that this doesn’t have to be one lane—and honestly, the most interesting careers rarely are.
🇵🇷 A Latina Voice in Travel (and Why It Matters)
Another layer of Jen’s story that really stayed with me is her perspective as a Latina travel writer—and the way she’s used that to shape her work.
“It’s actually been a gift.”
Her background and Spanish fluency have allowed her to tell richer, more nuanced stories across Latin America and the Caribbean—from contributing to guidebooks to highlighting local communities and voices that might otherwise be overlooked.
She’s also been recognized as a Top Latina Travel Expert, and it shows in the depth and authenticity of her work.
Because representation in travel storytelling isn’t just about who gets to go—it’s about who gets to tell the story.
✈️ Traveling Smarter (Not Just More)
Of course, we also got into the practical side of things—because Jen has figured out how to travel a lot without spending a fortune.
She regularly finds roundtrip international flights for $400 or less (yes, you read that correctly!).
Her approach is refreshingly straightforward:
Sign up for flight deal alerts
Use points and miles strategically
Stay flexible
And this mindset shift:
If you see a great deal… book it. Figure out the rest later.
If you want to try this approach, a few of the sites she recommends:
Her advice? Pick a couple, subscribe, and actually read the emails.
Because the best trips often start with a random message that says:
“Flights to Europe: $397 roundtrip.”
🚗 The Cross-Country Journey Everyone Should Be Watching
Just when you think Jen’s story couldn’t get more interesting… she’s about to take on her most ambitious journey yet.
This May, she’s hitting the road for a nearly month-long cross-country trip along the historic Lincoln Highway—the first road ever built to connect the United States coast to coast.
We’re talking:
New York City → San Francisco
Thousands of miles across the heart of the country
And her dog, Miles, riding shotgun the entire way
But this isn’t just a road trip for the sake of it.
It’s a storytelling project. A personal journey. And, in many ways, a love letter to America.
More Than a Road Trip
Jen is approaching this with the same intention she brings to everything she does.
Along the way, she’ll be:
Interviewing historians and locals
Highlighting small businesses, including women- and minority-owned brands
Visiting key landmarks along the route
Capturing stories that reflect what America looks like right now
Her goal is to create what she described as a kind of “digital time capsule”—something that goes beyond pretty photos and really captures the people and places that make up the country today.
And I love that she’s asking bigger questions:
What connects us?
What do we share?
And can a road originally built to unite the country still do that today?
Thoughtfully Planned (with Room for Magic)
If you listened to our conversation, you know Jen is incredibly intentional.
She’s mapped out daily routes (keeping driving to around three hours a day), planned key stops in advance, and is scheduling interviews along the way—while still leaving room to follow curiosity when something unexpected appears.
That balance—structure with a little spontaneity—is what makes a trip like this work.
And there’s also a deeply personal layer.
One stop she’s especially looking forward to is Ames, Iowa, where she’ll honor a former coworker who encouraged her to pursue writing.
A reminder that sometimes the most meaningful parts of a journey aren’t the ones you’d ever find in a guidebook.
Turning a Road Trip Into a Real Project
This trip is also a perfect example of how she’s built a true business around travel.
She’s partnered with TESSAN as a title sponsor, bringing the journey to life through her “Miles Across the USA” series.
She’ll be capturing video throughout the trip, with plans to potentially turn it into a documentary—layering in interviews, history, and real stories from the road.
It’s thoughtful, ambitious, and a smart reminder that travel today can be both creative and strategic.
👀 How to Follow Along
This is the kind of trip you don’t want to just read about after the fact—you’ll want to follow in real time.
Jen will be sharing the journey across:
Instagram (@jenonajetplane)
Her dog’s account (@puponajetplane)
Expect a mix of daily moments, behind-the-scenes glimpses, hidden gems, and an honest look at what it’s really like to spend weeks on the road.
🔥Rapid-Fire Favorites
Most chaotic travel moment:
Scratching a rental car in New Zealand (on a mountain road 😳)
Destination everyone should visit:
Jordan
Favorite travel apps:
Airbnb (always search for “Superhosts”)
Expedia
Marriott Bonvoy
Google Translate
Always in her carry-on:
A mask
Wipes
💫 Final Thoughts
What stayed with me after this conversation wasn’t just the travel tips—it was something deeper. You don’t have to overhaul your entire life to change it. Sometimes, all it takes is starting… with one trip. Jen didn’t have a master plan or some perfectly mapped-out vision. She just said yes to that first experience, then another, and kept going. And somewhere along the way, she created a life that looks completely different from the one she thought she was supposed to live—a life with more freedom, more intention, and a lot more adventure.
And honestly, that might be the best kind of travel story there is.
Meet Jen Ruiz
Jen Ruiz is a lawyer turned full-time travel content creator and author. She is a 6-time Amazon bestselling author, 3-time TEDx speaker and 7-time national award-winning travel journalist. She has been featured in The Washington Post, Forbes, and Daily Mail and named a Top Latina Travel Expert by Mitú and The Points Guy. She was the editor of Lonely Planet’s Central America guidebooks and is the solo female traveler behind Jen on a Jet Plane.
Wishing you safe & memorable travels always,
