A Bad Travel Agent Can Still Plan Great Adventures. Welcome to Vagabond Empires.

I had no idea how to start this project, so I decided the best place was with a confession. Come closer. I’ll whisper this.

Ready?

Whew. That feels good to get off my chest. Here’s a little story.

When I finished high school a year early, everyone expected I would head to college and take advantage of the head start. I flippantly told my family I wanted a gap year. I spent that year waking up my parents and young brothers rolling in at 6 or 7 in the morning, having spent the previous night in all-ages dance clubs in Berkeley or San Francisco, or at house parties in Santa Cruz.

When the year was up, my mother gave me a choice - college or a job. I chose job and became a children’s studio photographer at the local Kinderfoto in the mall. The hours were great. I made some cool friends, and it didn’t interfere with my nocturnal antics.

Plus, it was the mall. In the 80s. Like, what could be cooler?

Mother wasn’t amused. She thought taking a “menial” job would kick-start my aspirations into high gear. It did not. I was living my best John Hughes main character life.

Finally, she’d had enough and decided I had two options, since I wasn’t following the script in her head and going to college. I could become a hairdresser, or I could become a travel agent. She handed me two trade school brochures and told me to pick one by the end of the week, or move out of the house.

Harsh, but fair. I knew it was time to figure something out. I had a 1976 Ford Pinto, for pity’s sake. And that thing didn’t match my Pretty in Pink vibe.

It wasn’t a hard decision.

My yet-undiagnosed neurospicy brain couldn’t fathom the idea of touching hair all day. Major ick.

But to travel? Have adventures and see the world? #YesPleaseAndThankYou.

And so, two years later, I was a graduate of Echols International Travel Training Academy in San Francisco, class of D-47. The youngest ever. And for the next three decades, I navigated the ever-changing landscape of the retail travel industry.

But I was a terrible travel agent. I have no sense of direction. If I can’t see the mountains to the east and the ocean to the west, I am lost as a goose. I still don’t know where all the states are in the USA, much less Europe or Asia or Africa. Plus, there are too many airports with the same name. Did you know there’s a San Jose in Costa Rica? One of my clients discovered that one early morning when I booked them there instead of the California one. Also, Portland in Oregon and Maine are nowhere near each other. Fun fact.

Despite starting straight out of high school and rising to executive levels in the largest and most prestigious companies in the world… I was really — really — bad at getting people from point A to point B.

It was a fantastic thing that wasn’t what paid my bills. Lucky for me (and every potential traveler) there were people less directionally challenged that did the heavy lifting.

It was my job to make sense of the technology and to figure out hacks and shortcuts to power the business. And then teach the technology and hacks to people all over the world. 

That became my superpower. I’m good at that. I’m also good at rolling with the punches and figuring out travel hacks. Ask me anything about packing cubes, how to find Wi-Fi in the remotest of places, and the best way to navigate airfare and mileage programs.

Those are the puzzles I enjoy solving and talking about endlessly.

This project is designed to share how I can travel nearly full time and run my company remotely. I’ll give you a behind the scenes at the systems and tech, and I’ll also talk about time management and mental health stuff. That’s pretty important, I’ve discovered.

It’s both a travelogue with pretty pictures and video, and sage business advice from a 50-something woman that’s owned seven companies, travels mostly solo, and has health challenges.

And while I have a lot to say and share, sometimes what you’ll get are cautionary tales of what you should definitely not do.

That might be the best part. Sometimes shit goes south, and it’s hilarious.

I’ll invite you to laugh with me at the results of my being a bad travel agent (but an amazing technologist) while we have a virtual pint of something and chat about absurd things. Like how I miss trains in Copenhagen at 4am, or get in unmarked taxis in Mexico, or walk a mile in the wrong direction coming out of a train station with too many bags in the rain.

Because that’s what I hope this becomes. A virtual trip together as fellow vagabonds, swapping stories and building empires to sustain our wanderlust.

I hope that it’s inspirational and aspirational. I think the world is an amazing place filled with interesting people. You’re (obviously) one of them.

Pull up a chair, friend. Next up I’ll share the travelogue of this summer’s Europe 2024 “Chellenanigans Tour of Eight Countries in Eight Weeks!”

It’s a doozy.

Until next time,
Chelle