From International Housesitting to School Administrator Abroad

Teaching Traveling: Want a secret to affordable travel? Curious about working as a school administrator in another country?

Check out the inspiring story of how Sheila Dee came to become a school administrator in Thailand after taking a year-long trip around the world with her husband for less money than some Americans spend on rent, alone!

Sheila, tell us a bit about your background. 

Sheila: I never seem to do things the way others do. If there is a backwards way around something, it seems that is the path I take. For instance, I was on the 13-year plan to get my degree. During those 13 years, I was a corporate travel agent in California, and a process auditor in Arizona. I was in the middle of my bachelors degree when my job as a process auditor was outsourced to another country.

I thought I would take some time and relax, but that was not to be the case. I saw a teaching position at a Phoenix, Arizona charter school and I decided to apply. I really just wanted to see what the interview process was like, but in the end they offered me a 1st grade teaching position. It was exactly the grade level I wanted. I taught for two years before I finished my teaching degree. I didn’t have to student teach because I already had two years experience in my own classroom.

After receiving my degree in 2003, I switched to teaching 7th grade at a public school. I had always thought that 1st grade would be the grade level for me, but found my personality fit more with the 7th graders. They are snarky and I can joke around with them.

In 2004, because teaching a new subject and year level, coaching cross country track and track and field, and having a child in competitive hockey wasn’t enough, I decided to go back to school to get my masters in Curriculum, Instruction and Design. Once I tackled that, I decided yet another change was in order and left primary education for a job in the curriculum department at a university. Never one to sit still, I also taught and supervised student teachers from the university. Ultimately, I became the Dean of Curriculum at a small technical university.

And then I left Arizona. Well, the United States to be more precise.

TT: Ooo! Tell us how your career launched into international territory.

S: My most interesting travel story is that my husband and I spent a year traveling the world and only spent about $24,000 to do it. At the beginning of November 2014, we were looking to make a move to another state, when we read an article about a couple who started housesitting around the world in 1991 and were still going strong. We quickly started exploring the feasibility of us taking off and traveling the world in the same manner.

After much discussion, we announced to our families our plans (or lack thereof) and set about selling almost literally everything we owned. We we would play it by ear, taking the odd housesitting assignment around the world for a year. To keep our friends and family updated, we launched a blog and released weekly podcast episodes: The Opportunistic Travelers.

We had no real plans beyond our first stop in France for a three week housesit to watch two cats, three quail, and four chickens. It wasn’t until just a few days before we left that we lined up another place to stay, this time Copenhagen for a 2 week housesit watching a sweet pup called Tigo. After that, we made a stop in Brussels to see a new friend (and by “new” I mean someone inspired by our story who invited us to stay in his home, never having actually met us), and then it was off to England for six weeks to watch three cats and five dogs for two different housesitting assignments.

By March and still in England, we secured a three month assignment in Thailand, where we were to look after a beautiful cat… but the assignment wouldn’t begin until the end of May. That left us with a big hole in our calendar: one that was quickly filled by a friend of my husband. Her family keeps a vacation flat just outside of Santiago de Compostella, Spain that she offered up to us. She posted the keys to us while we were in England, and we were soon off to Spain for six weeks.

Following Spain, we popped into London to speak at a conference, and then spent a few days in Milan, Italy for the World’s Fair. After that, our three month adventure in SE Asia awaited us.

Making a long story short, we left Thailand to spent time in Vietnam riding the train, went to a swank condo in Hong Kong to watch a pair of sweet French bulldogs, and then headed back to Thailand for a speaking engagement and yet another housesit. From there, we visited our 3rd continent of the trip, spending two months in Australia, from Sydney, the Whitsundays, and Brisbane. During our Australia trip it was all about seeing friends and (yep, you guessed it) another housesitting gig.

At the end of 2015, we had traveled to 13 new countries. During that entire year of traveling the world, we only paid for about 30 days of hotel. That makes it a lot easier to spend money on things like flights, food, and excursions.

TT: Incredibly thrifty! How do you find your travel opportunities? 

S: Originally, our travel opportunities were all through housesits and friends. However, another opportunity came quite unexpectedly four months into our travels, as we found ourselves travel bloggers, getting asked to speak at conferences and to work with tourist boards. Since that time, we have worked with some major hotels, travel brands, and even CPG companies to provide content and coverage spanning our blog, my photography, and our podcast.

TT: Fascinating. How did you find the money to fund your travel? 

S: We funded our travels by selling just about everything. Before we left the U.S., I was posting things on Craigslist almost daily. We had what we called a Buy and Bye party where friends came to say goodbye but also buy something!

Additionally, I sold Sophia, my little red sports car. She is what truly supported our travels for the year. She is with a good family now and I get to see her when I am back in Phoenix.

TT: Ha! Tell us one moment from your travels that was particularly interesting.

S: We were housesitting in Thailand, but the hosts had a delay to the start of their trip. So we decided we would get out of their hair for a bit and head to a small island just a quick two-hour ferry ride away for my husband’s birthday. Our hosts called the night before to confirm the ferry would leave at 10 am.

The next day, our host family dropped us at the dock at 9:45 am but there was no ferry boat waiting for us. When we walked up to the ticket counter, they informed us the ferry left early (virtually unheard of in Thailand) but another would depart at 2 pm. Luckily my husband and I are very good at is entertaining ourselves, so we decided we’d just wander the docks for four hours.

We didn’t get 100 meters from the ticket counter when a Royal Thai police officer, in broken English, inquired into just what we had planned. When we managed to convey just wander around, he pointed to the back of his police truck and says get in. Hey, he had a gun.

So in we go, where we’re driven about a kilometer or so to a couple of ladies, a card table, some plastic containers of cash, and a sign above them that seemed to indicate departure times for a different ferry service. Not that there was a boat or a dock, but the officer clearly wanted us to buy tickets, So we did, after which we were loaded in the back of his police truck once again, off this time for several kilometers.

As we weave through the narrow, industrialized passageways, every Thai person that sees us (and there were only Thai people here) in the back can only stare and wonder just what we did to wind up in police custody in this part of town, where no tourist ever sets foot. That made for quite a story, which we happily retold during the first season (we are currently on season 4) of our podcast.

At the time we were dabbling in the journalistic-style of podcasting, recording the sounds around us as we had our adventures. (Oh, and we don’t do a podcast like that anymore. 12-14 hours of work to make 8 minutes of audio gets in the way of having fun traveling! Our format today is much more relaxed, which is a lot easier on us. And our audience seems to love the change, too!)

TT: Amazing. How have your travels impacted you in your career, and how have your travels impacted you as a person?

S: I think my travels have given me a different perspective on life. I am calmer and happier than I have ever been, which is reflected in how I teach. Once again, I feel the excitement about teaching just like I did during my first years teaching. I am enjoying teaching again! I am constantly learning (about my new adopted country and their cultures) and exploring new place; and I think that makes me a better person.

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

S: Good teachers are needed everywhere. If there is someplace you want to explore as a local, there is no better way than to do it as a teacher. If you are looking for a teaching position in Thailand the best site to look at is a site called ajarn.

Thailand is a great place to live and work. If you have questions, or just want to chat about teaching in Thailand, you can reach out to me at sheila.unwin at gmail dot com, or if you want to follow along with my husband and my travels, check out our website and podcast, The Opportunistic Travelers!

TT: Thanks so much, Sheila! Readers, what questions or comments do you have?