When I initially told people in 2023 that I was going to move to New Zealand (NZ) for a year to do a working holiday, they would often follow up to ask me why, or what I had hoped to achieve. Was it burnout? Was I trying to discover myself? Loneliness? Escapism? It was probably a mix of all the above, but more than anything, I just wanted to do it because I felt stagnant in my life.

In early 2020, I had this vague idea in my head that I would do some sort of long trip after graduating from university. In the labyrinth of my brain, I was angling for a possible six-to-eight week trip around India. I had only been to India once previously, and it felt somewhat embarrassing that I had not visited enough of the country in my lifetime, given my ancestral roots there.

In my head, this was was set to be a grand adventure, one of those “do this in your 20s before you enter the corporate grind” type of trips. That idea came to a screeching halt within a few weeks as reveries of mountains, hikes and forests were swiftly replaced with the starkness of isolation, ennui and stillness brought on by the pandemic. The adventure would have to wait, and I told myself that I would revisit this idea after working for about two years.

The sense of stagnation was first felt strongly towards the end of 2022, as I reached the two year mark at work. People around me were beginning to settle down, get married, look for BTOs1 and move to the “next phase” of life, while I was spending my weekday evenings trying to get better at DOTA2, reading obscure sports statistics on Wikipedia and running.

To be clear, I thoroughly enjoyed spending my time on these hobbies, but it just felt like something was missing. Despite doing well in most areas of my life, there was a spectre of emptiness which followed me around. The liminality of COVID also made me feel like I “skipped” two years of my 20s in an instant when life resumed to normal. It was in these moments when I began to revisit the prospect of a long trip, and that excited me.

Since I was a kid, I had this dream to move somewhere for a year where I knew no one and just travel. I first started searching for potential working visas and jobs in Europe, but there was not much luck. Singapore mainly offered working holiday visas to Australia and NZ. I read the travel blog of a Singaporean who did a working holiday in New Zealand, and that was enough for me to take a punt at this.

I had never been to NZ, nor did I know anyone who lived there. All I knew about NZ was that they had shot the Lord of the Rings there, so surely it must be a beautiful country right? I applied for the visa, and to my surprise, it was approved within a month. My first reaction was excitement, but panic soon set in. So far, my thoughts about travel were just fantasy, but now it was real.

In true Singaporean fashion, I wanted to ensure I had the strongest safety net possible. I tried to apply for a sabbatical from my job so that I could do the visa and come back. Unfortunately, this wasn’t successful. So my only options were to stay at my job and forgo the visa, or to leave my job and go ahead with the plan. No safety net, and lots of uncertainty.

A simple thought experiment helped me make my decision. If I didn’t go to NZ and stayed, I could see myself in my office wishing that I was in NZ. If I went to NZ, I was definitely not going to be thinking, “man, I wish I was in the office right now writing submissions and replying to emails.”

That’s not to say that I didn’t waver in making the decision. There were plenty of conversations with friends and family about going ahead with this. It took months of planning, worrying and self-assurance to finally pull the trigger. I told as many people as I could about my plans on purpose so that they would keep me accountable, since I find shame to be a powerful motivator. There would be nothing worse than telling everyone about a big life plan, only to back out and face the ensuing embarrassment.

At one point in 2023, I was even beginning to sound like the boy who cried wolf, as I told everyone that I was going to NZ, yet I seemed to still be in Singapore, showing up at parties and gatherings.

Snippets of actual conversations with friends

I finally made the plunge to move in March 2024. I don’t regret it at all, and it has been one of the best decisions I’ve made. As I am going to be here for a while, I wanted to document my travels to share them with my friends and family, and also use it as a form of digital archiving and self-reflection. For anyone who wishes to follow my travels, I will attempt to post semi-regularly, and include my travel photos as well. Til then, hope you enjoyed reading this, and I look forward to sharing more of my thoughts and travels with you.


  1. Build-to-Order flats, a form of public housing offered in Singapore to couples who intend to get married. Part of the “Singaporean Dream”. ↩︎
  2. Defense of the Ancients, a multiplayer online battle area game that sucks your soul and tests friendships. ↩︎