When Bill Strayer first dreamed about moving to Asia, Japan was always the goal.
Born in Colorado, Strayer went to college in Missouri and later moved to the Bay Area to work in tech. There, work trips across Asia introduced him to cultures he hadn’t encountered growing up.
As an adult, he participated in a homestay program in Japan three times, living with local families.
“That’s what really kicked me into gear for being in Japan,” Strayer, 63, told Business Insider. “I studied Japanese, I watched Japanese movies, I listened to Japanese music. I made 14 trips to Japan.”
Provided by Bill Strayer.
As his career evolved, Strayer accepted a role at a financial services company that eventually brought him to Hawaii.
“My company had a branch office in Honolulu. I thought, well, Honolulu is kind of on the way to Japan. I’ll just stay in Hawaii for two, three years and then eventually make it to Japan,” Strayer said.
What was meant to be a brief stop in Hawaii turned into 24 years, and the move to Japan never materialized.
Instead, Strayer left his job as a portfolio advisor after a few years and eventually started a new chapter in aviation, first flying cargo and later transporting hotel guests between Hawaiian islands.
And when it finally came time for him to retire, he moved to Bangkok instead.
Falling in love with a new city
While Strayer was living in Hawaii, the timing never seemed right for a move to Japan — in his 30s, retirement still felt far off. And his mother had moved to Hawaii full time after years of being a snowbird.
A two-week vacation through Southeast Asia in the early 2000s shifted his attention away from Japan. With just a day and a half in Bangkok, Thailand’s capital, he hired a driver to show him around — and fell in love with the city immediately.
Provided by Bill Strayer.
“This is so awesome,” Strayer said, recalling his reaction. “So I said, OK, next year I’m spending the whole two weeks in Bangkok. That’s what kicked it off.”
Every year after that, he would spend his two weeks of vacation in Thailand, learning more about the culture and its people. Over time, a realization set in: Japan was a place he loved to visit, but Thailand felt like somewhere he could actually live, especially since he wasn’t a fan of cold weather.
“There’s an extra point for Thailand; I’m not going to see a flake of snow,” he said.
After his mother died in 2021, Strayer decided to move forward with his plans. “There was no real reason for me to be in Hawaii anymore,” he said.
After retiring from his aviation job in October 2022 and applying for a retirement visa, he returned to Bangkok in May 2023.
Life in Bangkok
Strayer is part of a wider trend of people relocating to Thailand. Bangkok, in particular, has long been a hot spot for expats.
There were 102,189 foreigners living in the city at the end of 2024, according to the latest Thai government data.
Provided by Bill Strayer.
Strayer spent two weeks living in a hotel while looking for an apartment. With the help of a real estate agent, he found a two-bedroom condo about 20 minutes from the city center. Rent is 30,000 Thai baht monthly, or about $950, and he is now in his third year there.
His furnished apartment is close to the Bangkok Skytrain, making it easy for him to get around.
With a city so accessible, Strayer has found no shortage of things to do. A typical day starts with a light breakfast, followed by a workout at his apartment complex, before heading out for lunch.
Provided by Bill Strayer.
“I don’t cook, because there’s so much wonderful food out there on my doorstep that is inexpensive and delicious, far better than I could ever do,” he said.
A self-described foodie, he enjoys exploring new restaurants, and much of his social circle has grown out of those visits. One of his go-to spots is a small, traditional Thai restaurant that serves home-style dishes.
“I know the staff, they know me. Sometimes we get together outside of their work and stuff like that. That’s been fantastic,” Strayer said.
Many of his days end with a visit to one of Bangkok’s sky bars, where he watches the sunset.
“I’ve made it a mission to try to visit as many as I can,” he said. “No need to drink alcohol or anything like that, but just go ahead and hang out.”
Provided by Bill Strayer.
Even in retirement, Strayer hasn’t fully slowed down. He’s been trading the US stock market since the 1990s and still wakes up between 2 and 4 a.m. to do it.
He’s also built a small circle of expat friends in the city, including a Canadian retiree he met at the gym and another he connected with through YouTube, bonded by a shared interest in the stock market.
“I should spend more time at home, but there’s so much to see and do and people to meet that I have a hard time staying home,” Strayer added.
He continues to travel between Bangkok and Honolulu about three times a year, mostly to visit friends. But he doesn’t see himself returning to Hawaii permanently — at least not for now.
“I would not have this much fun in the US. I can tell you that right now,” he said.
Do you have a story to share about relocating to a new city? Contact this reporter at agoh@businessinsider.com.
