Transitioning from Teaching to Full-Time Travel and Remote Work

Teaching Traveling: Curious how to transition from teaching to full-time travel? Check out the story of “History Fangirl,” Stephanie Craig! Stephanie, tell us about yourself.

Stephanie: I’m originally from Edmond, Oklahoma. I went to the University of Kansas for college, where I spent my senior year as a recruiter for Teach For America. After college, I moved to Philadelphia where I taught math to middle and high school students as a Teach For America corps member (Philly ‘06).

After two years in the classroom, I realized full time teaching wasn’t for me. I’m in awe of my friends from TFA who stayed in the classroom or went on to be principals or found charter schools.

I moved on to a career in technology sales, but I didn’t like being disconnected from learning. I began saving up to travel full time in 2015, and last July I left my corporate sales job to travel full time.

TT: Wow! Tell us more about your travels.

S: I’ve been traveling to places that have always intrigued me: old monasteries and secluded churches, communist monuments, and unrecognized countries. I recently returned from two weeks in Romania, Moldova, and Ukraine, where I got to explore all of these passions.

I spent seven hours with an Uber driver to get to Horezu, an Orthodox Monastery in the Carpathian Mountains, found one of the points of the Struve Geodetic Arc in Moldova, and spent a day in the Soviet breakaway republic of Transnistria. I capped the two weeks with a day in Chernobyl. It was an inspiring trip full of beauty and sadness, with constant reminders of how the past can never be truly whitewashed from the present.

TT: Amazing. How do you find your travel opportunities?

S: My trips are often planned on a whim. If a friend wants to go somewhere, then we’ll go. But if no one’s available, I’ll plan something on my own. Now that I’m working completely online, I travel about half the time and spend the other half in my new Bulgarian base of Sofia.

TT: Love it. How do you pay for your travels?

S: I work as a social media consultant. Since I work completely online, I’m able to go wherever there’s a good wifi connection. I work from the road, so I might miss a place or two when I’m in a city, but it’s worth it for me to be able to spend the rest of my time on my passions.

TT: Nice. Tell us a moment from your travels that was particularly powerful.

S: Last year I was driving through the Troodos mountains in Cyprus, trying to get to some of the painted churches, which are a collection of medieval Orthodox chapels that collectively comprise a UNESCO World Heritage Site.

I had planned to go to three of them, but arrived at my final stop just as the caretaker was locking up. Instead of turning me away, she had me follow her to her home and lent me her spare key. I had an hour in a 13th century chapel all to myself. It was incredible.

TT: So neat! Now, how have your travels impacted you as a person and in your career?

S: No matter what job I had, I never stopped thinking about travel. Now that I travel all the time, I’m trying to make it more valuable for others. History travel is what interests me the most, hence my blog, History Fangirl, whose tagline is “A Global History Geek-Out.”

That said, I know a lot of people who love history aren’t interested in seeing places in person. I’m looking to bring the history and stories to folks who don’t have plans to go on their own. For example, my article, “Normandy in Pictures” aims to bring the location of D-Day alive.

TT: What advice do you have for teachers who are dreaming of travel, or travelers dreaming of teaching?

S: For the most rewarding trips, connect your travel to your passions.

TT: Great advice, Stephanie! Readers, what questions or comments do you have?