True Confessions from Being a Travel Agent Digital Nomad

Confession time: Being a travel agent who’s been to over 30 countries as a digital nomad doesn’t mean I have it all figured out. Far from it!

I’m also a mom and a wife who’s spent months living in campervans, bustling cities, and tiny villages with my family.

Between juggling client calls and chasing my kid around, I’ve had my fair share of travel fails, unexpected friendships, and moments that made me laugh (or cry) on the road.

What I’ve learned is that the best travel stories don’t come from perfectly planned itineraries – they come from the messy, real, and often hilarious moments that happen when you slow down and really live somewhere.

So here’s a peek behind the scenes at some of my most honest travel agent confessions – because if you think we’ve got it all together, think again!

Confession #1: I’m a Travel Agent Who Gets Lost (A Lot)

I’m a Chicagoan. From the city, not the suburbs. I lived there for over 16 years, it’s where I met my husband, and it’s where my son was born.

And I’ve used public transit all over the world in many languages, but navigating Tokyo’s metro nearly broke me.

The language and writing system were unfamiliar, and the local etiquette that says you don’t run down the escalators (because it’s rude) meant I ended up getting my family on the wrong train at least one-third of the time.

If you see a frazzled mom sprinting down the stairs in Tokyo, that’s probably me! At least we made it on and off the bullet train without issues.

Navigating Tokyo’s metro might have been my most humbling moment, but it’s far from the only time travel has thrown me a curveball. Sometimes, the best parts of travel come from the people we meet along the way.

Confession #2: I Regularly Make Friends with Strangers Who Become My Local Guides

While campervanning in New Zealand, we met an incredible mom who happened to be one of the Riders of Rohan in the Lord of the Rings trilogy.

She didn’t just share stories about the movies; she told us about an epic stargazing spot and a bakery that quickly became our breakfast favorite. I still dream about those New Zealand pies!

These kinds of connections brought the country – and my favorite movie series – to life in a way no tour ever could.

Confession #3: I’m Obsessed with Finding the Perfect Kid-Friendly Snack

When traveling with kids, food is everything. I’ve spent way too much time hunting down the best local treats that are both delicious and kid-approved.

Sometimes it’s a weird fruit – like Rambutans in Costa Rica – and sometimes a bakery in a tiny town in Argentina has the best alfajores of our lives – but it’s always a highlight of the day.

When we go on cruises, we have a rule that my kid has to try one new, non-dessert food every single day.

It might be something from the buffet at breakfast or an appetizer at dinner. Thanks to this rule, he discovered a new love for shrimp cocktail on our Antarctic cruise!

Traveling with kids means there’s always a fun twist to the usual routine, especially when it comes to food.

Confession #4: Work-Life Balance is Weird When Living on the Go

Speaking of kids, working on the road means juggling work and family moments that can get pretty entertaining – or chaotic.

Once, during a client call, my Wi-Fi suddenly froze. Turns out, my tween was video chatting with a friend on another continent while simultaneously playing a video game with that same friend – who was screen sharing his gameplay!

Multitasking at its finest! But seriously, when we’re always traveling the balance between working on travel planning and living the planned travel does get pretty blurry.

Confession #5: I’ve Seen the Same Tourist Spot from Every Possible Angle

I spent a month in Japan during cherry blossom season, and spent weeks searching for the best spot at the best time. It’s NOT Ueno Park in Tokyo on a Sunday afternoon!

Here’s my insider tip: Sunrise is consistently the best time to see the cherry blossoms with minimal crowds anywhere in the country.

Watching the soft pink petals glow in the early morning light, with very few people around, is a magical experience that’s worth the early wake-up call.

And when it comes to travel timing, I’ve learned a few tricks that make all the difference, like the best way to enjoy Japan’s iconic cherry blossoms. Or taking epic photos at Machu Picchu!

Confession #6: I’m Secretly a Souvenir Hoarder

I try to keep packing light, but somehow I always come away from a place with a collection of quirky souvenirs – from handmade crafts to local snacks – that remind me of the stories behind each place.

We love collecting souvenirs that tell a story. In New Zealand, we bought a crocheted glow worm at the Waitomo Glow Worm Caves. In Japan, we picked up some chopsticks for my sushi-obsessed kiddo.

Plus, we have a tradition of buying him a t-shirt in every new country we visit so that one day, we can make a massive quilt out of them. It’s a fun way to hold onto memories and watch his travel journey grow.

Confession #7: I’ve Had to Say “No” to Some Experiences Because of Work

Even though I’m a travel agent, balancing work commitments means sometimes missing out on spontaneous adventures. It’s a tough balance, but it makes me appreciate the trips I do get to take even more.

During two months in Cambodia, we became good friends with our neighbors. They invited us to a game night one evening, and it sounded like so much fun – but I had to say no because I had client calls scheduled that I couldn’t miss.

After all, night for me might be morning for them so I work weird hours sometimes. It’s one of those moments where the balance between work and travel life feels especially real.

But the epic views I get from some work locations makes it all worthwhile!

Confession #8: I’m Always Planning My Next Trip, Even When I’m on One

I’m always on a trip and always planning the next one. The travel bug is relentless! But instead of burning me out, helping my clients plan their adventures actually fuels my addiction.

Every new itinerary I create, every destination I research, reminds me why I love living my family’s offbeat life so much.

Still, no matter where I am or what’s on my plate, I’m always dreaming up the next adventure – and that’s what keeps this lifestyle so addictive.

What These Confessions Have Taught Me

Travel isn’t always picture-perfect – and that’s exactly why I love it.

These confessions remind me that the real magic of travel happens in the unexpected moments: getting lost, making new friends, trying strange foods, and balancing work and family in imperfect but joyful ways.

Slow travel has taught me patience and flexibility, and it’s deepened my appreciation for the people and places behind the postcards.

Like the postcard I mailed to my family from the southernmost post office on earth…in Ushuaia, Argentina. And it actually arrived a few weeks later!

Slow travel over such a long period has also made me a better travel agent because I know firsthand what families need to make their trips smoother, more authentic, and truly memorable.

At the end of the day, travel is about embracing the messy, the surprising, and the wonderful – and sharing those stories with others is one of the best parts of my job.

The Takeaway

Travel isn’t about perfection-it’s about the unexpected moments, the detours, the snacks, and the friendships that sneak up on you when you least expect them.

These confessions are a reminder that the best parts of travel often come from the messy, real-life experiences that don’t make it into the glossy brochures.

So whether you’re dreaming of your next family adventure or already on the road somewhere new, remember to embrace the imperfect and enjoy the ride. Because that’s where the real magic happens.

Happy travels – and may your journeys be full of wonderful confessions of your own!