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Why I quit my job to be a less occasional traveller in 2016

Some of you might have heard by now – I just quit my job to travel – so I’m going to be a slightly more frequent traveller, just for a little while.

I know I’m probably going to get a bunch of questions, so I thought I’d answer them here.




One thing I’ve always wanted to try is longer-term travel. None of my overseas travels to date have been any longer than 3 weeks – my Portugal trip in 2014 was the longest trip I have taken in recent memory. I have not lived or worked overseas, nor had the experience of really slow, unscheduled travel. None of these new experiences can be achieved while I’m in my current full-time position, no matter how high up I climb.

As The Occasional Traveller, I firmly believe that you can enjoy a fulfilling life of travel while holding a full-time job. I have done so quite respectably for the past 6 years (!) since I started TOT – managing to eke out more than a month’s worth of time overseas with half that amount of leave every year. You can see how I do that on my yearly travel round ups. I still don’t think quitting your job to travel is for everyone either.


you can have it all – work and travel don’t cancel each other out if you balance them right!

Being a dedicated travel blogger on top of living a life of wanderlust and working a full-time job though – that’s a little bit trickier, and I’m just one of many bloggers out there who have managed to keep all those balls in the air, but just barely. 2015 was a pretty stellar year for me – I visited many new places and managed to work with tourism boards and companies who recognise the work I put in.

But now, I want something a little more out of travelling – new unknown experiences, a different style of travel to sate that wanderlust, and something I’ve always believed is that it comes down to your priorities – and right now mine is focused on my travels.

“You’re very brave” say a lot of people, and that’s a rather loaded phrase to me and I usually just give a shrug, because what more can you say? I recognise that it’s not a decision many take in pragmatic Singapore, yet there are so many who have gone before me (I’m practically a mid-life crisis / travel blogger cliche – quitting my job to travel) that it’s hard for me to see what makes my decision special at all. It’s just something I need to do.



Osaka - Umeda Sky Building Fortune front

What will my path be like in 2016?

On paper, it feels like a terrible time to quit my job – growing unrest across the globe, the economy is in flux and might be facing recession – I was in a pretty stable government job and doing quite well to boot, with a promotion last year, good reviews and I enjoyed my work and friends. Giving that up for the unknown and unemployment seems a little rash.

But… is there ever really a right / proper time to do this?

What I should highlight is that while it may seem a sudden decision to many, this isn’t a spur of the moment thought or some abrupt life epiphany – friends will know that I have been thinking about doing this for at least two years – I had initially planned for this to be a 30th birthday milestone, but my family was shifting homes that year so it just was not a good time to go.

I have also been in this job for 4.5 years – by my peers’ standards that is a comparatively long time. It is a fairly comfortable job and I learned a lot from it, but it was becoming increasingly frustrating as well due to myriad reasons. There were no pull factors to stay, and an increasing number of reasons to go. Maybe it’s just my personal threshold – I lasted about 4 years in the previous job as well. That short break between jobs was what led me to my first solo trip, so perhaps it’s time for another first :)

It might have been a small sign, but while I was having an internal panic about handing in my letter, this old post by Zen Pencils  popped up onto my Facebook feed. A little moment of resonance and serendipity perhaps?

“‘Someday’ is a disease that will take your dreams to the grave with you – Timothy Ferriss”



Portugal - Cabo da Roca Jumpshot Kickup


In the year ahead, I intend to travel more and travel longer. With my new found freedom, I’m going to get on the road and spend more time than I usually would on it. I do have some commitments to keep at home so I won’t be completely nomadic for the year ahead, but I will be spending longer stretches just travelling.

There are broad plans in place, but I know I’m Europe-bound from June to September and probably headed to Latin America from November till early 2017 at least. In between, expect smaller stints around Asia – I’m still finalising some plans and I’ll share them here on the blog once they are more definite. (See where I finally landed up in this round up post)

Osaka - Umeda Sky Building Sketch

More writing and blogging for sure

I definitely want to spend more time writing this year – I feel like I’ve been a little remiss in my blogging and I hope to make up for that this year. I’m still going to write useful and inspirational pieces for the busy travel loving office worker, but alongside those pieces you will see a little more insight on my personal journey as someone taking a career break. I’m not encouraging anyone to up and quit their job just because it’s the sexy thing to do – but if it’s something you are seriously considering, I hope my story and foibles will help you find the best way to do so yourself.

For my lovely readers, occasional travellers or not, I know you are generally a quiet sorta bunch who don’t like to comment much, but I do know you’re out there reading and I thank you for all the support. I’d like to hear from you though – what do you like about what you’ve read on The Occasional Traveller so far, and what do you want to see more of? Any words of advice or encouragement for me?



Singapore Street Art - Perak Hotel Money Boy Close up

Money doesn’t drop from the sky unfortunately~

I’ve amassed some savings from all these years of work, and I think it is a lot easier to save when you are a single person (or you know, married to travel like I am). I am pretty lucky to not be in debt, nor have any major loans to pay off, or have any other situations holding me back. Anyway there are people who have travelled and done much more with far less than me – those are the people worth admiring.

I’m not looking to take on any serious full-time jobs in this year – that’s not what this break is about; I need to recharge and focus on travel, but I’m looking for freelance opportunities in marketing, public relations, travel writing, content production and social media management that can be done remotely, which will help to defray my travel costs. Do drop me a mail if you know of anything suitable!

Also happy to share the nitty gritty behind the scenes look at my journey, whether it’s costs or itinerary, if that’s what you guys want to know more about!


And the Million-Dollar Question – WHAT’S NEXT?

Portugal - Lisbon Roman Galleries Shadow Wall

What does the future hold? What will I want in a year’s time?

Who knows? I intend to just spend a year travelling, then come back to Singapore and rejoin the corporate world again – I know myself enough to know that I’ll miss home and need to come back for awhile. But you know what, a year is a long time for things to happen, let’s just see what happens next.

And also if you aren’t already following me on social media, now would be a good time to do so as that’s where you’ll get the most up-to-date notes on where I am and what I’m up to. I’m probably going to be most active on Instagram @jac_theocctrav, but you’ll see updates on Facebook, Twitter and maybe the odd Snapchat @jac_theocctrav as well.

I’m gonna be focusing on travelling and seeing new places on this journey- friends in Europe and South America – I’m coming to visit y’all and shamelessly bunk on your couch if I can :P I will probably be working with companies or doing some freelance stuff on the side to help defray travel costs, and at the end of it all I’m happy to share with everyone the nitty gritty about what you need to do for a trip like this.

Who else out there has big travel plans in 2016? Share them here so we can cheer each other on!


Thursday 4th of January 2018

look forward to following your new adventures tours. I’m sadly not in a position to travel full-time now but when I collect Huge money i will travel everywhere.

Jaclynn Seah

Thursday 4th of January 2018

you don't need lots of money to travel! you just need to pick the right places and be prudent, and no need to rush either, take your time!


Tuesday 15th of November 2016

Hi Jaclynn,

Kudos to you! I just did a three-month trip in South America after finishing a two-year job contract. Wish I could have travelled longer but I've got bills to pay! Feel free to let me know if you need any information on South America. Otherwise, have fun and stay safe on your travels! ;)

Jaclynn Seah

Tuesday 15th of November 2016

Thanks Geraldine! I definitely will need some info, will let you know when I narrow it down some :)

Well you can still squeeze in some travels even with work - that's what The Occasional Traveller is all about anyway... happy travels!


Saturday 5th of November 2016

Hey there - I like your philosophy! I'm doing something similar to you end of year (quitting my corporate job and have a one way ticket to SE Asia), and boy, is it scary!

I like the idea of doing it for a few months then coming back to reality. I actually tend to think once we've been on the road for more than a few months, it'll be nice to come home. Long term travel will have a lot to teach us - for sure.

Best of luck on your journey :)

Jaclynn Seah

Sunday 6th of November 2016

great to hear from you Amber, and if you ever drop by Singapore, feel free to give a holler! happy to hang out if we're both in town :)

one of my favourite things about travel has always been coming back home :) good luck for your travels too!


Sunday 16th of October 2016

Thats a great step and decision. I hope to be a full time traveler soon! :)

Jaclynn Seah

Monday 17th of October 2016

Good luck with that! :)


Tuesday 1st of March 2016

Aloha Jaclynn! Chanced upon your blog, wanted to learn more on self defense before embarking on a years' round-Europe trip. Good luck for all the adventures! Keep on wriitng!

Jaclynn Seah

Tuesday 1st of March 2016

hello! thank you and I hope your Europe trip is awesome! I'm headed there too but just for a few months :)