I medically retired from the military, and my wife and I decided to move to Thailand. After taking a trip there for a Muay Thai tournament a year prior, she yearned to go back and explore more. Her descriptions of it made it sound like a fever dream that I was unable to attend due to my job. Feeling lost and looking for direction, and living in a high-cost-of-living area, we agreed to leave Thailand when our lease expired in October of 2025.
Making this decision in December of 2024 gave us about 10 months to work with. It certainly felt like plenty of time at the moment, but looking back on it, it’s amazing we were able to pull it off at all. I certainly learned a lot throughout the whole experience, and reflecting on it now, here’s what I learned during this transition.
(Image Credits: Carlos Menendez)
Visa research was my first wake-up call. No one tells you how much admin it takes to legally stay long-term, and the application process – gathering bank statements, contracts, business registration – took weeks of back-and-forth before we finally got approved. The research took me a little over a month, and we eventually settled on the Destination Thailand Visa, or DTV for short. It’s a wonderful option with two separate tracks to apply through, these being the digital nomad track nd the Thai soft power track.
The digital nomad track is what we chose, thanks to her photography business based out of Hawaii and her ability to work remotely, although we seriously considered the soft powtrackrac, which requires an acceptance letter to a Muay Thai gym, a school of some kind (typically a Thai cooking class), or an acceptance letter for hospital treatment. The requirements for our track included showing proof of our business and remote-work ability, as well as proof of financial means totaling 500,000 Thai Baht, which translates to around $16,000 to $17,000.
We applied directly through the Thai consulate based in Los Angeles, which I should make a note of, saying they were always extremely helpful and responsive to any questions I had. After a few months of work gathering the necessary documents and bank statements, we had our visas sent to us digitally. It’s safe to say, this was the easiest part of preparing for our move.
(Image Credits: Carlos Menendez)
My next few concerns were more straightforward. I arranged an Airbnb for our first 3 months in Bangkok, planning to scout out a longer-term option. Health insurance was trickier, and taught me another valuable lesson; In some circumstances, it’s necessary to outsource tasks to people more informed. After some googling, I reached out to Pacific Prime, who helped me review several plans and subscribe to one that worked best at a price we could afford.
The next challenge was bringing our pets. This involved getting an import permit and updating all their vaccinations. It was a tedious process filled with emails and veterinary appointments, but we eventually had the pets approved on the same flight we would be on. All told, we spent $5,000 – $8,000 before we even got on the plane.
(Image Credits: Carlos Menendez)
My education continued after we touched down in Bangkok. Customs took me about 12 hours to navigate in order to get our pet, thanks to a combination of language barriers, “ghost agents” offering to do all the work for me at a ridiculously inflated price, and fatigue from traveling to an entirely different time zone. Our pets were pretty dehydrated by the time I got them, which taught another lesson: you can never spend too much on your pets’ comfort.
Our next lesson came at the Airbnb, where security immediately told us that pets weren’t allowed on the property. After some heated words were exchanged with our host, who had stated this wouldn’t be an issue, we were able to confirm our stay for the night. Unfortunately, our dog needed to have an emergency surgery due to her stomach twisting, so she would be staying with the vet for a while. We were able to stay at our Airbnb for ten days while I scrambled to find better accommodations. Again, outsourcing saved the day, and we found an estate agent who did the legwork and found an outstanding pet-friendly apartment in the Ekkamai/Thonglor area.
(Image Credits: Carlos Menendez)
I was convinced I was being cosmically punished in some way, given everything that went wrong at first. After pushing past it, I wish someone had told me that yes, things are going to go wrong because moving is hard and messy, and international moves even more so, but once the dust settles, the life we want can finally take shape. I can’t wait to share it with you all.
(Image Credits: Carlos Menendez)
