What if a quarter-life crisis is exactly what you needed?
Most people fear uncertainty and falling off the rails. For Gabe Chia, 24, it was the moment when everything finally clicked.
One breakup, a one-way ticket, and one big leap of faith later, he’s now running three businesses from wherever he wants to be – and it all started with a decision to step away from formal education.
The Turning Point
It wasn’t a grand breakthrough that sparked Gabe’s shift in direction. It was a breakup and a growing sense of disconnect with the life he was leading, which ultimately changed his perspective on everything.
Gabe, whose following now amasses over 43,000 followers on Instagram, is widely known for his cinematic storytelling and hook-driven reels. His content focuses on his journey of figuring life out and building a business after stepping away from university to explore what life could look like beyond the conventional path.
In August 2022, Gabe was enrolled in Singapore Management University’s Business Administration course, following a path that felt much less like a choice and more like a default.
But after his five-year relationship ended, he realised something deeper was missing.
“I hated my life,” he told me bluntly over Zoom. “After the breakup, I had nothing holding me back. So I thought to myself, why don’t I just do what I want to do for the next six months or a year?”
How a Micro-Retirement Sparked a New Way of Living
Gabe stepped away from school with no concrete plan in mind. Instead, he was in search of clarity, an intentional break to reflect, travel, and discover what truly mattered to him.
The heartbreak, along with the disillusionment of school, gave him the perspective that he needed to start taking more risks.
Micro-retirement has been a growing concept among younger generations, in which individuals – particularly Gen Zs – take extended, intentional breaks from their careers or studies to travel, reflect, or pursue other interests.
Essentially, it normalises the idea of taking breaks even at a young age, contrary to what we have been taught to believe in society, where retirement can only be earned after working most of adulthood.
Unlike traditional retirement, micro-retirement is about hitting the pause button to gain clarity and pursuing activities that realign with one’s values. These breaks can spark creativity, prevent burnout, and help individuals reconnect with what truly matters.
Taking the Leap of Faith
That decision became a catalyst for a year of couch-surfing in strangers’ homes across the world, building three businesses, and exploring what a meaningful life could look like outside Singapore’s usual path of stability.
With no degree, no job lined up, and no real plan, Gabe did what many wouldn’t dare to do – he booked a one-way ticket out of Singapore.
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After buying a one-way ticket to Melbourne, life seemed like a movie. He made it look effortless – at least, from his social media profile.
When I spoke with Gabe, he confessed that, on the contrary, he actually spent “close to nothing” travelling the past year.
Instead, he slept on couches – often of strangers, sometimes of creators he reached out to or those who reached out to him – and spent most of his days creating content and figuring things out on the go.
The very first house he crashed was in Melbourne, with a fellow Singaporean who allowed him to stay there.
In New York, he lived rent-free for two months, and the stranger who let him stay has since become one of his best friends.
Within the last year, Gabe has travelled to cities such as Toronto, Melbourne, Lisbon and connected with fellow content creators he once admired behind the screen.
To the conventional Singaporean, what Gabe does sounds spontaneous, even reckless. But for him, it was deeply intentional. At the time, he didn’t have many close friends. He describes himself as someone who was constantly in “provider mode” – focused on business, money, and growth, but emotionally disconnected.
“After the breakup, I realised money didn’t mean anything if I didn’t have people to share it with,” he says.
“I think what I did was quite dangerous – just sleeping with strangers. But I guess I was ready to die at any time. I just wanted to live my life. If it’s not now, then when?”
Convincing his parents, he admits, wasn’t easy. While they were supportive, it took time for them to come around, especially in a culture where the university degree is still seen as a non-negotiable.
But once they saw that he was building something he truly enjoyed, they came on board.
“Is This Just a Phase?”
In Singapore, choosing to step away from formal education is often seen as a temporary detour at best. For Gabe, this stigma wasn’t unfamiliar.
“Internally, I was very scared,” he says. “I had no idea what I was doing half the time. But externally, I had to project confidence. I had to act like I knew what I was doing, even when I didn’t.”
Having both fear and confidence simultaneously became part of the process. Gabe acknowledges the anxiety of stepping into the unknown, but also something he calls a necessary “delusion” – the idea that in order to do something extraordinary, you sometimes have to believe in the impossible.
Content creation, however, wasn’t new to Gabe. As a child, he acted on local television, and later studied film at the School of the Arts (SOTA). That creative exposure stayed with him, and stepping away from school became a chance to finally return to what had always made him feel alive.
“All my friends who are doing really well, making seven to eight figures, they all have a bit of that delusion. Like, yeah, bro, I can do anything.”
“For me, it was more of, how can I create a lifestyle that I enjoy on a day-to-day basis and still call it work?”
Despite running three businesses, Gabe says that he doesn’t feel like he’s working at all.
The goal of pursuing a “micro-retirement” is to wake up every day excited about what he does, regardless of whether it fits the conventional mould.
What Does It Take to Leave Stability Behind?
It’s easy to admire someone who leaves everything behind to pursue their dream. It’s much harder to talk about what that actually takes.
Mentally, the hardest part was the uncertainty. Emotionally, it took something even deeper: a willingness to let go of what people might think, and that meant facing the discomfort of doing something new.
“Inside, I was scared. But I think I was just delusional enough to believe it could work. And sometimes, you need that delusion to push through.”
Financially, it meant a willingness to go out of your comfort zone. Gabe kept costs low by staying with acquaintances, strangers and friends. “I lived in New York City for free for two months. That’s unheard of. But I was willing to live differently.”
What kept him going was the level of support he had from his fellow peers. He surrounded himself with other creators, people who were honest enough to critique his ideas and generous enough to support his growth.
“Even though I’m a solo founder, I owe so much of my progress to the people around me.”
Redefining Success
Success used to be defined by a number. In one of his earlier videos, Gabe declared he wouldn’t return to Singapore until he was making $100,000 a month.
But as the months passed and the conversations deepened, his definition of success has evolved.
“I don’t want to be seen as just the guy chasing money anymore,” he says. “That’s not what I stand for.”
For the 24-year-old, success looks less like a dollar figure and more like freedom: waking up excited about doing work that feels aligned, building meaningful relationships, travelling, and one day, starting a family.
“My life goal has always been to get married and have kids,” he tells me. “Everything I’m doing now will lead me there eventually.”
What’s Next?
Now back in Singapore, Gabe is in the process of launching his next venture: a cohort-based bootcamp for content creation.
Instead of one-on-one coaching, the programme will bring together marketing teams, startups, and creators from around the world into a six-week crash course.
“I wanted it to be a training institution. Each week, I will teach something different, and we’ll even bring in guest speakers.”
It’s his most scalable idea yet, and one he hopes will bring him one step closer to turning Viral College into the content school he’s always imagined.
When I ask what advice he’d give to others considering a similar leap or embark on their own journey of micro-retirement, he doesn’t hesitate.
“Failure is just a step closer to where you want to be. If you knew you were 100 failures away from hitting your big win, wouldn’t you be excited to keep failing to get there?”
“Try more things”, he says.
As Gabe says: If not now, then when?
Sometimes, stepping back is the first step forward. Would you take a career break to find yourself? Let us know!