The Breaking Point

Tan vividly recalls the harrowing experience: So after the entire retreat, we were on our way back to the airport. That was when we got into a really, really bad car accident where the van we were on rolled at least five times. He added, Somehow, by God’s grace, every one of us survived. This brush with death became a catalyst for profound introspection.

The question that lingered in Tan’s mind was pivotal: Hey, if I were to die at that point, would I have been happy with the life that I chose to lead? This reflection sparked a journey of self-revelation and a radical shift in priorities.

Trading cubicles for Culture

Inspired by this newfound perspective, Tan and his partner, Joanna Wong, made a bold decision: they relinquished thier lucrative tech jobs to embark on a journey of global exploration. Their decision was fueled by a desire for fulfillment beyond financial success and a yearning to experience life on their own terms.

Wong articulated the feeling of being trapped in the daily grind: I think when you are in a job, sometimes you can get very busy with the work, and you don’t have the mental space and capacity to even think about what you actually want to do. I didn’t have the time to think about my future. Tan echoed this sentiment, expressing a desire for purpose beyond mere financial gain: I didn’t see how closing deals on a day-to-day basis would make me feel fulfilled, besides the financial aspects of it. I couldn’t see how selling tech software will make the world a better place.

Finding Home, Redefining Life

Their adventure began in Bali, where they spent a month recovering from burnout and contemplating their travel goals. This initial period allowed them to recalibrate and define what they sought from their journey.

But on where to live, I think a lot of us always take that as a default. We don’t really get that chance to travel with the objective of deciding eventually, ‘Do we want to continue living in Singapore, or do we prefer somewhere else?’

Darien Tan

Since then, Tan and wong have explored Indonesia, Thailand, and China, remaining open to the possibility of returning to Singapore. They finance their travels through savings, rental income from their apartment, and freelance work, adhering to a monthly budget of 3,000 Singapore dollars.

Tan explained, We give ourselves a monthly budget of 3,000 Singapore dollars.On some months,we overspend so we try to average it out. That has been a good budget for us so far. we generally can afford the things we want to eat and the places to stay.We don’t feel that we are compromising much in terms of cleanliness or safety.

Despite societal pressures to climb the corporate ladder, Tan and Wong remain unfazed.Tan stated, Anxiety usually comes whenever there is no plan. But for us, we are happy with the idea of our savings dwindling. Their philosophy centers on prioritizing experiences over deferred gratification, choosing to spend their money doing things we want to do in life rather than postponing it for an uncertain future.