Singapore Expat Life: 28 Years of Career Success and Quiet Guilt

Kris LeBoutillier grew up in Upstate New York near Lake Erie, dreaming of a life traveling the world. After working as an editor in New York City, a job opportunity led him to Singapore in what was expected to be a short-term posting. Instead, he remained there for 28 years, building a career that took him across Australia, Vietnam, Cambodia, Thailand, and India.

While his location provided the perfect base for his work as a photojournalist, the distance created a quiet guilt regarding his aging mother. He visited twice yearly but felt he wasn't there enough when she needed him. Today, he is raising a family in Singapore but worries about his children's connection to their American heritage. Despite the emotional toll, he views his expat experience as the realization of a childhood ambition.

Kris LeBoutillier grew up on the shores of Lake Erie in a town just south of Buffalo, New York. He describes a childhood where ice was something you chiseled off a car in winter, not something dropped into a drink. Life on a tropical island felt like a pipe dream.

As a high school student, he was the "geeky kid" who was excited to read stories in Time and The New York Times about exotic, far-off places. He knew early on that he wanted a job allowing him to experience global events firsthand. A semester abroad in France cemented this ambition, where he lived with a family renting to an American expat who casually discussed Swiss ski holidays and escapes to Greece and Turkey.

By age 21, he had decided on that life, asking why he should work in "boring" New York or Chicago when he could aim for Paris, Hong Kong, or London. After several years working as an editor in New York City, his then-wife received a job offer in Singapore. What they anticipated would be a posting of just a few years turned into decades.

The move to Singapore provided the jolt LeBoutillier's career needed. In 2000, he decided to pursue his dream of becoming a photojournalist full-time. His location made him a standout candidate as Asia entered a travel boom and magazine editors needed photographers on the ground.

He describes himself as being in the "right place at the perfect moment." Singapore served as the perfect base for assignments across the region. He could be ready to go anywhere in Southeast Asia with just a few hours' notice. His work included shooting for National Geographic Traveler across Australia, Vietnam, Cambodia, Thailand, and India.

Eventually, his photography career evolved into something more permanent and corporate. He transitioned into the role of a content director, producing and directing videos across the region. This shift represented a natural evolution for a writer-photographer in a world rapidly moving toward digital content.

Living overseas for nearly three decades changed LeBoutillier, but it came with a significant cost. His mother grew older and sick, moved into a managed care facility, and eventually passed away suddenly. He made every effort to visit twice a year, specifically in the summer and around Christmas.

Despite these efforts, he carried a tinge of guilt and remorse that he wasn't there more often. On one of his last trips back before she died, his mother asked him, "Haven't you been in Singapore long enough?" While she was always supportive of his choices, as she approached 80 and her health declined, she wanted him closer to home.

He acknowledges that while she received the care she needed in the nursing home, there was no substitute for his personal presence and the stories about his life overseas. When asked if he was selfish, he admits perhaps, but maintains he would never trade the life he has.

LeBoutillier remarried three years ago and is raising a family in Singapore with his wife, Jamie. He has a 9-year-old daughter from a previous marriage and a toddler son. Both children hold US passports, and he believes they deserve an American identity and a place to put down roots.

Although the children have visited the US to meet cousins and his oldest friends, they have never had the chance to live there or fully experience life as Americans. A recent conversation with his daughter highlighted this disconnect; when he mentioned she had visited Manhattan as a toddler, she responded, "Where is that?"

This realization was stark for LeBoutillier. He feels his children should know the country that shaped who he is. While he is unsure if he will return to the US himself because everything is different now, he absolutely recommends an expat life to others. He got the life he dreamed of as a kid reading about the rest of the world.