He turned 50 and realized the entrepreneur grind wasn't worth it. 2 years later, he retired to Chiang Mai.

• Turning 50 led Arinjay Jain to rethink how he wanted to spend the next few decades of his life.
• He traded his IT sales career for early retirement in Chiang Mai, Thailand.
• He now lives in a one-bedroom apartment that costs about $425 a month.

When Arinjay Jain turned 50, he was sitting in yet another meeting when it hit him: "What am I doing here?"

Jain hadn't always questioned the grind.

He had moved from India to Singapore in 2013, when the IT company he worked for opened a local office. After changing jobs a few times, he cofounded a small IT services startup in 2016.

He originally planned to build the company, sell it, and cash out. But as the years passed, the finish line felt increasingly distant.

"I thought, this is looking like several years away still, and I will have to work very hard to make it happen," Jain, now 53, told Business Insider.

At that point, he was no longer sure the stress of running his own company justified the reward. Around the same time, several real estate investments Jain had made in India appreciated significantly, giving him the financial security to consider stepping away.

"So then, why am I wasting my years?" he said.

Soon after, he began researching where he might want to spend the next chapter of his life. He knew he didn't want to go back to India.

While researching where to retire in Southeast Asia, a friend encouraged him to check out Chiang Mai, a city in northern Thailand he'd never visited.

In April 2023, five days in the second-largest Thai city sold him on the idea, and he threw himself into research about retirement visas and living costs.

By October 2023, when his lease was up for renewal, he decided against staying in Singapore.

Jain spent a couple of months visiting family and traveling around Asia. In February 2024, he arrived in Chiang Mai.

A new base in northern Thailand

February is often considered the start of the burning season in Chiang Mai, where farmers burn agricultural waste to clear their fields, often causing haze to drift into the city.

"I landed here in the worst possible time, but I still loved it," Jain said.

Thailand offers several long-stay visa options, and Jain holds a retirement visa.

While the Thai government publishes overall foreign resident figures, it does not appear to release a regular public count of retirement visa holders.

The latest civil registration data shows that 163,036 foreigners — not just retirees — lived in Chiang Mai in 2024, a level broadly comparable to a decade ago. That amounts to about 9% of the province's roughly 1.8 million residents.

Jain connected with a real-estate agent through Facebook and viewed several units before choosing his current one-bedroom condo near Nimman, a trendy, cosmopolitan neighborhood known for its café scene, chic boutiques, and international restaurants.

Rent is 14,000 Thai baht, or about $425, each month. His apartment building comes with a pool and a gym.

Jain says he tries to keep his monthly expenses between 40,000 and 45,000 Thai baht. In months when he travels, his expenses can reach around 60,000 Thai baht.

"For a lot of people from Western countries, the cost of living is a major attraction," he said. "For somebody from India, it's two or three times what I spent back home."

Still, Jain said his decision was driven more by lifestyle than money. He's grown comfortable with Chiang Mai's slower tempo, its sense of safety, and what he describes as a culture of respect and patience.

"Everybody likes to avoid stress, right? I'm very happy not to have stress living here," he said.

Life after the grind

That slower rhythm now shapes his days as a retiree.

Jain starts most mornings at the gym, then prepares a quick breakfast at home and does some household chores. Some afternoons, he plays golf at a nearby driving range. On other days, he joins a hiking group and heads out to explore waterfalls and trails around Chiang Mai.

In the evenings, he enjoys going for walks at nearby Chiang Mai University, whose scenic campus is a popular spot not just for students, but also locals across the city.

While he enjoys being around people, building deeper connections with locals has been more challenging, in part due to the language barrier.

Even though the city has a thriving expat scene, many tend to gravitate toward others from their own countries or from similar backgrounds.

Jain says he occasionally joins activity groups to stay social.

"But ideally, what I would like to do is become part of the local communities," he said. "That takes time, and the effort has to come from my side in terms of learning the language, but it's not easy."

Jain said he expects to stay in Chiang Mai for the foreseeable future, but he knows there are variables he can't control.

Visa rules can change, and retiring early means planning for decades ahead in an era of longer life expectancy.

"I have to plan for like 35 to 40 years," Jain said. "Look at all the changes that have happened in the last 20 years. It's difficult to imagine what might happen in the next 20 years."

For now, he said, he's content where he is.