Solo Travel: The Empowering Journey with Jen Ruiz – Episode 9

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Solo Travel Summary

In this episode, Jen Ruiz shares her journey from corporate attorney to solo female traveler, content creator, and entrepreneur. She discusses the empowering lessons learned through solo adventures, balancing work and travel, and the challenges of exploring new places. Jen also offers tips on staying safe, dining alone, and navigating the digital space, while emphasizing the importance of diversifying income streams and knowing your worth in brand collaborations. Whether you’re an experienced traveler or just starting out, Jen’s insights provide inspiration and practical advice for building a flexible, fulfilling career. Follow Jen on socials at @JenOnAJetPlane and us at @BonVoyageBesties

Key Takeaways

Balancing Travel and Work
Jen Ruiz shares her journey of taking 12 trips in 12 months while maintaining a full-time job, highlighting the possibility of balancing travel with professional commitments.

Empowerment Through Travel
Jen emphasizes the empowering nature of solo travel, especially for women, as a means to gain confidence and independence.

Overcoming Challenges
The discussion includes anecdotes about overcoming travel mishaps and the resilience required to navigate unexpected situations.

Transitioning Careers
Jen talks about her transition from a corporate career to becoming a full-time content creator, underscoring the importance of diversifying income streams.

Content Creation Realities
The conversation sheds light on the challenges and misconceptions of being a travel content creator, including the need for compensation and the hard work behind the scenes.

Personal Growth
Travel is portrayed as a tool for personal growth and self-discovery, with Jen sharing her experiences of finding clarity and purpose through her journeys.

Navigating the Digital Space
Jen discusses the importance of understanding the digital content creation landscape, including the need for professionalism and strategic pitching.

Age and Travel
The video challenges societal norms about age and travel, encouraging women to embrace travel at any stage of life.

Building a Brand
Jen highlights the significance of building a personal brand and the continuous effort required to maintain and grow it.

Future Aspirations
Jen shares her future plans, including writing a sequel to her book, aimed at inspiring women to use travel as a means of empowerment.

Listen on APPLE PODCASTS | SPOTIFY | YOUTUBE

Solo Travel: The Empowering Journey

Think solo travel is only for people who’ve ditched their nine-to-five and gone fully nomadic? Think again. Travel author and attorney-turned-content-creator Jen Ruiz, the woman behind the beloved brand Jen on a Jet Plane, built her entire travel empire while still showing up to court on Monday mornings.

In her debut book 12 Trips in 12 Months, Jen chronicles how she took 20 trips in a single year before her 30th birthday, all while maintaining a full-time legal career. She joined us on Bon Voyage Besties to talk about what it really takes to make solo travel work, how to stay safe on the road as a woman, and why she believes now is exactly the right time to book that flight.

Solo Travel Doesn’t Require a Career Change

One of the biggest myths Jen busts right out of the gate: you don’t have to quit your job to be a passionate solo traveler.

In fact, she believes the building phase (ex. the side hustles, the travel hacking, the careful trip planning while still employed) is an essential part of the journey.

“For many people, you end up being somebody that’s working a full-time job while you are building those income streams that allow you to ultimately become nomadic,” Jen told us. Her $70 round-trip flight to Aruba and $38 flight to New Zealand weren’t accidents, after all. They were the result of years of intentional deal-hunting, which eventually became the foundation of her first self-published book.

The takeaway for aspiring solo travelers: you don’t need a dramatic life overhaul. You need a flight deal and a willingness to use your PTO strategically.

How to Start Solo Travel (Even If You’re Nervous)

Jen’s advice for first-time solo travelers is refreshingly practical.

Start close to home. A solo day trip in your own city, a weekend in a neighboring state. These small adventures build the confidence muscle you’ll need for bigger trips abroad.

When you’re ready to go international, she recommends starting somewhere with a shared language. “It just takes away a level of possible distress if you’re somewhere that you’re not understanding what you’re reading, what you’re seeing, what people are saying.” Destinations like Australia, New Zealand, Ireland, and Kenya (where English is widely spoken) make excellent entry points for first-time solo international travelers.

Research, she emphasizes, is your greatest safety tool. Know where you’re going before you get there. Pre-arrange your transportation. Share your itinerary with people you trust back home. Register with the U.S. Embassy’s free STEP program if you’re an American traveling abroad.

“Knowledge is power,” Jen says. “If you’re not walking around looking lost, trying to figure out the day of where you’re going — that screams tourist.”

Solo Travel Safety Tips for Women

When it comes to solo travel safety, Jen is both realistic and empowering. Daytime exploring tends to feel bold and freeing, but nighttime is when nerves can creep in and that’s completely valid.

Her secret weapon? Organized nighttime tours. In Athens, she joined a cocktail bar tour. In Amsterdam, she did a guided historical walking tour of the red light district. In Osaka, she joined a back alley food tour. “You have this safe container,” she explained, “and you’re incentivized by the tour guide to make sure you get there and back safely.”

It’s advice we’ve taken to heart on Bon Voyage Besties. Solo travel doesn’t mean doing everything alone. It means having the freedom to choose how you experience a destination, including opting into a group when it makes sense.

The Magic of Traveling Solo

Beyond the logistics, Jen speaks beautifully about why solo travel is so transformative, especially for women. When you’re solo, you’re fully open to the destination. There’s no buffer, no internal social negotiation. You interact with everyone.

That openness led to one of her most memorable travel moments: being spontaneously serenaded at a small opera in Florence. She’d arrived early, chatted with the staff out of genuine curiosity, and by the end of the night, an Italian tenor was belting out a song about the women of Granada — just for her, two feet away. “It’s inevitable,” she says. “When people see that you’re there, that you’re curious, that you have this positive, excited energy — they want to share special things about where they live.”

Solo travel also gives you radical permission to be selfish in the best possible way. Unlimited afternoon tea for one? Go for it. A $300 omakase sushi counter in Tokyo? Zero regrets. No one to talk you out of the dessert menu. No one to rush you. Just you, and what you want today.

On Resilience: When Things Go Wrong

Even the most experienced solo travelers have moments of pure chaos. Jen told us about the time she was dropped at the wrong port during a cruise in Eastern Europe. Yeeeeeah, it was bad. No service, no ride, a boat leaving soon, and a literal industrial chasm between her and the ship. Her solution? Scream across the water until the captain came out.

“I was not leaving there until somebody called somebody from the boat,” she laughed. And she made it.

Solo travel builds a kind of resilience you can’t manufacture any other way. Every wrong bus, canceled flight, and language barrier teaches you that you are more resourceful than you knew. And you collect the best stories in the process.

There’s No Expiration Date on Solo Travel

Perhaps Jen’s most powerful message: there is no age limit on solo travel, and there is no “right” time to start. Whether you’re a new empty nester in your forties, a twenty-something with a full-time job, or someone approaching retirement dreaming of a month-long cruise through Southeast Asia. The world is waiting for you.

“The beauty of this journey,” Jen says, “is being on your own timeline and discovering yourself along the way.”

Her upcoming sequel to 12 Trips in 12 Months picks up at her 35th birthday and follows a year of travel, including the real-life Hogwarts Express in Scotland, a Kintsugi class in Japan, and Easter Island, as a journey of healing, self-worth, and total unapologetic freedom.

So if you’ve been sitting on the idea of solo travel, Jen’s advice is simple: book the flight first. Figure out the details later.

Listen on APPLE PODCASTS | SPOTIFY | YOUTUBE

You can find Jen at @jenonajetplane on all social platforms and at jenonajetplane.com. Her book 12 Trips in 12 Months is available on Amazon. Listen to the full episode of Bon Voyage Besties on Spotify, Apple Podcasts, YouTube, and wherever you get your podcasts.