What Was I Thinking When I Quit My Job and Moved To Thailand?

My mission in life is not merely to survive, but to thrive, and to do so with some passion, some compassion, some humor, and some style.

Maya Angelou

Teaching English in Thailand

In the summer of 2013, I quit my job and left the U.S. to live in Southeast Asia.  My first goal was to obtain a CELTA certification so I would have the best qualifications to teach English.  I hoped to find some work as an English teacher and supplement my savings to stay in Thailand, while I continued to search for other remote work opportunities.

My classmates and our students during the farewell party for the CELTA certification class.
My classmates and our students during the farewell party for the CELTA certification class.

Securing a remote work job was my main goal, before I even thought of teaching, I was searching for a job online that would allow me to work from any location and earn a U.S. salary. I had been working in the Information Technology field for the previous 14 years.  I’ve worked from home before and known many others who have, so it did not seem so far-fetched to me. I knew it would be difficult but not impossible.

Unfortunately, I did not receive my CELTA certification although I completed the course.

I still could have taught English, but the prospects in Chiang Mai were very slim for an inexperienced English teacher, to receive a salary I was comfortable with.  My next alternative was to head down to Bangkok but I just wasn’t ready for the hectic lifestyle of Bangkok.

Instead, after I completed the course I focused on developing this blog, traveling around Northern Thailand and learning as much as I could about Thai language and culture.

One of many afternoons spent working in the many cool coffee shops around Chiang Mai.
I spent an afternoon at the Marble Arch working on this blog.  One of the many cool coffee shops in Chiang Mai.

I ended up living in Thailand for approximately 5 months and Bali, Indonesia for 1 month.  The main reason I came home to the states is that I was running low on savings and I really wanted a much larger cushion if I was going to really commit to living abroad long term.  I decided it would be best to come back home to find a contract job save money and try again the next year.

The Precursor

In early 2012, I lost my home to foreclosure even while I was working a comfortable I.T. job with a decent salary.

As a result, I moved back in with my parents and put my “stuff” in storage.  As traumatic as the whole ordeal was for me, I was convinced by a friend that a trip to Thailand would lift my spirits. Despite some anxiety, about traveling to Asia, I was brimming with excitement for the unknown.

During that first trip to Thailand in 2012, I realized that I had been missing out on something.  I had never felt so alive.  I was totally out of my comfort zone and it wasn’t uncomfortable or unpleasant.  I felt liberated and I loved it.

Kayaking from Railay to Phra Nang Beach in 2012.
Kayaking from Railay to Phra Nang Beach in 2012.

I’ve always loved to travel.

However, it was usually only an average of 1-2 weeks a year, if at all, for the last 20 years since graduating college. I would often dream of living in a foreign country, immersing myself in a new culture and learning a new language, but at the age of 41, I still hadn’t even really tried.  I only talked about it, based on the short experiences I had visiting places like Costa Rica, Jamaica, and Barbados.

I think the mindset that I had before the Thailand trip was that I lost everything, but instead I learned that I had gained something.  I gained freedom.

Freedom from an expensive mortgage and a greedy home association. I looked at apartments right after I lost my house but my father convinced me it would be foolish to start spending money on renting an expensive apartment when I could stay with him and my mother, save up and pay off my credit cards.

View of the world from my desk.
View of the world from my desk.

When I returned home from my whirlwind vacation in Thailand, I was still so excited by the whole adventure, I couldn’t stop thinking about it.

I settled back into the daily office routine sitting in my office cubicle and after a few days I gradually became overwhelmed with depression because that brief moment of freedom was gone, but I knew something had to change.

I knew many expatriates were spending their retirement in Thailand either full-time or a few months out of the year.  But then later I started finding stories about digital nomads, travel bloggers and entrepreneurs living in Chiang Mai saving money, living very simply and cheaply.

I knew their stories were true because now I had experienced it.  They were enjoying the benefits of eating out every night, getting massages regularly and taking weekend retreats to the islands or other exotic nearby countries, at a fraction of the cost of what it would cost in the U.S. I never would have thought of living there as an option if I hadn’t visited it myself.

A desk is a terrible place from which to view the world. World Travel.

I decided, that I had to go back and for much longer than two weeks. I spent the next year planning, saving, and selling all of my furniture and household items through Craigslist.

I kept it all in storage for a year and found that was also a waste of money.

The smaller items that I couldn’t sell and or use again in the future, I repacked in plastic bins and stored those in my parent’s attic.

My Jeep was the last thing I sold before i left for Thailand.
My Jeep was the last thing I sold before I left for Thailand.  I kind of miss it, but he was a gas guzzler anyway!

What’s next?

Stepping outside of my comfort zone has opened my eyes to so many new opportunities that I had never thought of before. I started this blog to share some of my adventures and hardships.  There is a potential to make some supplemental income, with it but I am not depending on that.

I am writing and designing it because I actually enjoy it!

It is just another step I am taking towards pursuing a location-independent lifestyle that focuses on enjoying many unique and adventurous experiences with new cultures and exotic locations.

I’ve learned so much from my time living in Thailand and even more since I returned home to Florida. 

Simply because I have had plenty of time to reflect on my mistakes and what I can do better in the future.

One of the most influential sources of information for me that sparked a change in my perspective about my career and lifestyle has been The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich by Timothy Ferris.

I won’t go into the details of his book in this post, but to summarize shortly, his methods promote a more productive way of working and allow for more time to live your life doing more of the things you enjoy while still generating an income.

I still have a lot to learn in regard to how to make this location-independent lifestyle possible and sustainable, but I have never been so focused and determined in my life.

After all, traveling has always been my passion, so, I might as well put all of my efforts into making it happen.

I knew and still know for certain that working for a corporation 9-to-5, five days a week, living paycheck to paycheck and buying things I don’t really need, and putting off really “living”  till I am 70, is not the path I want to follow.

So…what was I thinking when I quit my job and moved to Thailand?

Well, I was thinking, I am tired of running the rat race.  The truth is the American Dream is not the key to happiness.  

Well not for me.  

Most of the things I thought I always needed I don’t really need.

When you are bombarded with the allure of fancy cars, jewelry, new gadgets, phones, clothing, new homes, and the need for frequent home renovations which are consistently advertised on television, radio, and the internet, it might appear that is all we are working for.

I really believe stepping away from all of the noise and unplugging is the only way to discover what you really want out of life.

Family and friends are the most important to me, and I see that we have all been chasing a dream, competing with each other, and working to acquire all of these material things that are only passing fads and are also perishable.

Sure we are all working to make a living, and I want to make a living, but my priorities have changed, and my perspective has changed.

My idea of living and quality of life has changed.

Snorkeling Deerfield-Optim-1

Moving to Thailand was a way for me to separate myself from my old ways of thinking, challenge myself, and learn more than I’ve ever learned in a classroom.

I will never be the same, and it’s only getting better as I reflect on my experiences, despite the hardships I am facing now back in the states.

Would I do it again?


I will return to Chiang Mai and focus on some other business ventures I have in mind.  I will reveal some of those ideas as I progress in making them work for me.  Chiang Mai is only one of many places I plan to live in and learn from in the future, but that is where I will begin again.

South America and Europe are also on my radar. I have no regrets about the decision I made to pack it all up and leave the United States.  

So far, it has been the best time of my life and I feel only the beginning.

I still have many stories to write about!  I just can’t wait to see what new opportunities will open up the next time I leave my comfort zone.

I am only working now toward my next plan of action and I hope you will stick around to see what happens. 🙂

Author and Website Designer | Website | + posts

Brian Dennis is a full-time software engineer, some-time traveler and location-independent entrepreneur.

Chasing his passions in addition to travel in recent years has become a little challenging but even more fulfilling with his wife Betina and 1-year old son Divine.

Currently he is located in S. Florida and continues to share what he's learned with travel tips, guides and some motivating inspiration to encourage others to do more and experience more outside of their comfort zones.

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