The career break – if not now, then when?


This is it.

I’m quitting my job to travel the world taking a career break.

Well, if you’ve known me personally, I’ve been toying with this idea in my head for a really long time but for the past many years, the idea did not develop further.

This time round, age has caught up on me and if I don’t make the decision fast, I might not have a chance to do it anymore.

Well, apologies for the dramatic introduction but.. I’M GOING TO NEW ZEALAND FOR WORKING HOLIDAY!!

The initial plan was to go to Australia (back in 2017 when they first announced that Singaporeans are now eligible for Australia’s Work & Travel). I even wrote a blog post about my excitement of the news back in June 2017 and the happy/sad news was that I got a job before the applications started in August 2017. Well, everything happens for a reason, so I guess this current employment gave me some time to save up money and as time goes by, I decided to settle for New Zealand, instead of Australia. (Will work on a NZ vs Australia Working Holiday post in the near future but the easiest to understand reason was that the NZ application was cheaper and simpler as compared to Australia.) The downside of choosing NZ was that the Working Holiday Visa (WHV) was only valid for six months (Australia is twelve months) but I guess it’s a semi-blessing as it brings me back to reality early and re-start my job search next Jan 2020. *Conflicted; as always*

Right now, as I type (March 2019), I still have the intention to return by Jan 2020. No one knows how six months can change my thoughts.

Maybe I’ll earn enough money or perhaps secure a stable full-time job somewhere else or perhaps earn enough money via my blogging and end up living the life of a real travel blogger. Let’s see which continent of the world I’ll be in when I read my future me email on the 31st of December 2019. I write an email to my future self every year so it’s fun to read my own self-reflections 365 days later.

There’s just so much to prepare for my NZ trip, but chances are I’ll get lazy and not do anything at all

  • Decide on which city I would want to fly in to – Auckland, Wellington or Christchurch?
  • Booking air tickets – it’s gonna be a one-way trip via my hard-earned Krisflyer miles
  • Purchasing insurance (for unknown x no. of months)
  • Figuring out how to secure jobs/interview prior to my arrival
  • Booking accommodation (at least for the first week)

I started with a ‘dark’ post on my blog earlier in Jan 2019. If you are keen to read about my random thoughts and where I am at when it comes to planning for NZ, you can fall back on this post while I try to figure out how I can better organize the information better.


It’s so hard to resign.

As much as I’ve thought through the process many times over a couple of months, there’s just so much uncertainty (of emotions) involved. I’m not usually a quitter but.. if not now, then when? This had not been an easy decision but as I shared my plans with the people around me, I do get a wide spectrum of comments ranging from

  • sarcasm: ‘wow, so brave. did you strike lottery’
  • concern: ‘are you sure you’re making the right decision? What are you gonna do when you’re back’
  • worried: ‘why are you going alone?’
  • support: ‘you should do it.’
  • regret: ‘how I wish I did it, now I’m overaged (or have other commitments)’

gosh, feels like i’m exaggerating the whole process but the agony, dilemma, and uncertainty is real.

I do get worried all the time for all the right and wrong reason but I guess it’s time I change my mindset (7th habits) and instead of seeing this six months as unemployment, I should see it as an experiential and educational phase in my life – where I get to leave my baggage behind and worry about myself, and not for anyone else.

This is gonna be an important post and I foresee myself reading this multiple times when I’m there or in the future.

Oh wells, by the time this post gets published, I should have already given the white envelope =p

Wish me luck. ^^

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