Welcome, traveler!
I’m Jessie, and I believe that life is a journey.
One meant to be shaped by your own compass—not someone else’s map.
But let’s be real: forging your own path, especially as a solo traveler, isn’t always easy.
Outside voices from family, friends, even social media can drown out your inner calling.
That dream trip? That desire to explore the world solo or start a travel blog? It’s easy to let those longings simmer on the back burner, waiting for "someday."
Trust me, I’ve been there. (You can read my full story below 😊)
Let me ask you something, though:
If you don’t set off on the path to making your boldest travel dreams happen now…then when?
Do you really want to look back one day, wondering what if? 🤔
What if you'd booked that solo trip and discovered how empowering it is to explore the world on your own terms? 🤸♀️
What if you'd spent that summer abroad, immersing yourself in new cultures and landscapes that left a permanent mark on your soul? 🌋
What if you'd finally stopped letting doubts or outside opinions hold you back from building a life of adventure, meaning, and freedom? ✨
Because here’s the truth: you absolutely have the power to create that kind of journey.
One filled with active adventures, transformative experiences, and moments that go far beyond the guidebook.
And I’d love to help you get there. ✈️
Jessie on a Journey offers an honest look into the adventures, advice, and detours of your travel blogging BFF (me!).
Whether you’re a solo traveler craving spontaneity, a wanderer drawn to wild landscapes, or a curious soul who feels most alive in the unknown, this is the destination for bringing more meaning and fulfillment to your journey.
Empower your next journey with real-talk and resources for exploring the world — and experiencing life — #BeyondTheGuidebook.
And for those wanting to learn how to turn their love of travel into income, you’ll find loads of free blogging resources as well as step-by-step strategies via written guides and The Profitable Travel Blogger Podcast.
Just a few of the MANY lessons you’ll learn from this travel blog:
🗽 64 Best Non-Touristy Things To Do In NYC (From A Local)
💻 How To Become A Digital Nomad With No Experience
✈️ 25 Important Tips For Flying Alone For The First Time
🔐 17 Safety Essentials You Can't Afford Not To Pack
🏔 How To Spend 2 Unforgettable Weeks In Kyrgyzstan
🏝 15 Best Caribbean Islands For Solo Travel
🥾 Hiking The Stunning "Path Of The Gods" On Italy's Amalfi Coast
😂 16 Short, Funny Travel Stories That Will Make You Laugh Out Loud
What I Do
How can I help you
travel toward your best life?
Unique Travel Experiences
Snag free resources for travelers wanting to explore the world beyond the guidebook, like travel personality quizzes, trip planning printables, and more!
NYC
Photo Journeys
I offer NYC photo tours, private photoshoots, and custom trip planning, perfect for capturing memories while exploring the city!
Travel Solo Confidence
You don't need a partner to explore the globe. Learn how to feel confident while mastering the art of traveling solo in this free e-mail course.
Profitable travel blogging
Along with my travel blogging courses and membership, I offer a ton of free resources to help you grow your blog's traffic & income!
My Story
The short version
Once upon a time, there was a young woman who was told the key to a fulfilling life was a 9-to-5 job, two weeks of vacation, and a steady climb up the corporate ladder.
She gave it a try — until a failed group trip to Europe turned into her first solo adventure.
That unexpected journey changed everything.
Hooked on the freedom of solo travel, she left corporate life behind and launched Jessie on a Journey, a blog that lets her travel the world, work from anywhere, and help others do the same.
She traded suits for suitcases, and now her “office” is wherever adventure calls.
The end. (Kind of.) 📖
The Longer Version
Have you ever felt like the “right path” was the “wrong path” for you?
Yeah, I’ve been there. 😅
I was born and raised in New York — where I am also a certified sightseeing guide — and grew up traveling, mostly Caribbean cruises and US road trips.
Travel was always present, but it wasn’t until college that it started to take hold of something deeper.
While earning my BA/MA in Communication & Rhetoric, I studied abroad in Australia — my first real taste of independence abroad. I was hooked.
Soon after, I planned a backpacking trip through Europe with friends. Until one by one, they dropped out.
I almost bailed too…but something told me to go anyway. It wasn’t just a trip. It was my first true solo adventure.
What started as a backup plan turned into a life-changing experience. The freedom, the confidence, the ability to follow my own curiosity — I didn’t want to give that up.
That solo leap opened the door to everything that followed: a homestay in Ghana, cycling through India, teaching English in Thailand, backpacking South America solo.
The more I traveled, the more I craved that feeling of being pushed just beyond what I thought I could handle — and growing because of it.
Still, I tried to follow the expected route. I got a “real job” for a bit, only to learn I wouldn’t be allowed any vacation time for six months, and even then, just two weeks a year.
The office felt more like confinement than stability. I was stuck under fluorescent lights, living on someone else’s schedule, following someone else’s rules.
So I left. Not without fear. And definitely not with everyone’s approval. But I knew I couldn’t spend my life living by someone else’s definition of success.
I waitressed full-time while figuring out my next move — a job that let me pay the bills and travel when the bug hit.
Then one day, I stumbled upon a travel writing course (funny enough, I now teach a few of my own).
That course changed everything. It showed me I could combine my love for travel and storytelling and turn it into a career.
That’s how Jessie on a Journey was born — a solo female travel blog rooted in active adventure, cultural immersion, responsible tourism, and helping others go beyond the guidebook.
Today, I split my time between NYC and the road.
I still travel solo more often than not.
I still get nervous before big trips.
And I still believe that the best journeys are the ones that push you just a little past your comfort zone.
Travel — even in small doses — has the power to shift your perspective, grow your confidence, and help you build a life that’s fully your own. I created this blog to help you experience that.
Whether you're dreaming of your first solo trip, planning an offbeat escape, or just searching for something more meaningful, you're in the right place.
Let’s rewrite the map together. 🗺✈️
THE NEW STRATEGY FOR PROFITABLE TRAVEL BLOGGING
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