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Preparing for longer trips – how much to plan (or not)

Beyond my usual travel-helpful posts on the blog, I plan to get a little more personal in the Year of my Career Break – talk a little more about what goes on behind the scenes and how I’m managing my year of travel ahead. Perhaps others out there might feel comforted that you aren’t the only one facing some of these concerns, or if you are planning your own trip, learn from my experiences.

Career Break - Happy Travelling

A present from my younger sister – how cute is this balloon!


Week 1 of my Career Break – I’m still finding it a bit surreal not to be going back to work after almost 8 years of employment. I’m still enjoying the novelty of waking up at noon, but am surprisingly busy this week – I need to rev up and get into gear soon. It’s hard to tell the days when you’re not tracking the weekend as closely

In other news, I landed an internship position for a month in Japan thanks to Japan Travel! Hello Sakura season~ I’ve timed that for end March so I can also catch the Setouchi Triennale, so suddenly my time for planning seems even shorter than before. Expect for me to be in Japan in April and to revisit my old favourite Taiwan in May, then I swing back to Singapore for a brief break before heading up to Europe over the summer! Gonna take a 2 week detour to Kenya thanks to the amazing Helen! I will be back in Singapore for family stuff in October, hoping to do Jogjakarta and then take off to TBEX Asia in Philippines and I’m hoping to make my way to South America in the later part of the year.

my RTW Trip Plan

I found this in my archives – I did a map-making class 3 years ago and had a think about the countries I really want to visit. It’s nice to see that I’ve apparently had pretty consistent thinking about where I want to go all this time! I might not do Iceland or Morocco this time around though but I still want to go there some time!


People assume that when you ‘take a break to travel’, it automatically means you’re going to backpack your way around the world non-stop for an entire year, going wherever your heart takes you. It’s a romantic ideal – I imagined being a lot less tethered to plans, just booking flights and accommodation the day before I travelled to that place, deciding on a whim to go or stray from my path…

But you know what? That is so far from the truth.

For me, right now that is.

I could probably go be a free spirit and wander if I wanted to, but at this early planning stage, I’m already seeing how it’s not going to be the case. Far from it even – I’m probably going to be doing more complicated planning than for my short occasional trips. I actually have a budget sheet. And several Google Maps with a ton of pins. I still feel like I’m on finite time with an infinite number of possibilities, albeit on a much larger and longer scale than before – I’m trying to plan multiple travels within the span of a year, and that’s before I’ve narrowed it down to more specific locations.

Maybe it’s the micro-manager in me who likes to be well prepared and making the best use of my time and money. Or that I am a creature of certain habit that likes a certain amount of predictability and low drama. Truthfully, it’s quite overwhelming deciding what exactly I’m going to do and where I’m going to go. And these are the questions that everyone (and I mean EVERYONE and their mother) asks you when you tell them you just quit your job to travel.

“Where are you going?”

“Have you booked your trips?”

“Wow bet you’re travelling the world!”

It is surprisingly tricky to answer casually sometimes. So don’t take offense if I just shrug and say “I’m still planning”, because I’m just tired of repeating my very vague plans and it really is a lot more complicated than it seems.


Well I haven’t resorted to guidebooks yet… but the number of tabs I have open makes me sometimes feel like I’m doing some serious browsing…  Pic by Jenn Vargas via Flickr CC



Tentatively, I’ve set aside a sum of money to cover my entire year of travels, including any sort of emergencies that might come up, and I’m doing little odd jobs here and there to help cover costs. Let’s see how the first few months go before I revise this again), but it is still a finite sum that I need to manage. To stretch my dollar and travels, I need to try and find the lowest possible costs, and you just can’t do that with last-minute bookings. The best flight deals especially require that you book them early.


The awesome Singaporean passport means I don’t often have to think about getting Visas, but on longer journeys you do have to make sure you don’t overstay – I had to go read about the Schengen Visa for Europe quite closely when planning and booking my Europe trip to make sure I don’t end up overstaying and getting fined. And for certain countries I will need to procure visas in advance, so it’s not something I can just do on the fly.

Peak Seasons

So it turns out that I’m going to be in Europe from June to September, which hits peak tourist season in July-August. With high tourist traffic, there’s no way I can visit some of the popular places without making some advance bookings. I planned to be in Japan from April to May, but also realized upon research that I would be encountering Japan’s Golden Week, so my plans had to be pushed up instead. Just winging it might mean no accommodation and sky-high plane tickets, something I can’t afford without a steady paycheck!

Peace of mind

It’s pretty important to me to know that I have certain things under control – that major purchases like flights and accommodation are accounted for so I don’t get stuck some place without a roof over my head or a plan. All this results in me being much less grumpy and able to enjoy my travels better – I’m going to be hella cranky if I had to worry about all these things throughout my travels! I believe in getting it done and out of the way so I can enjoy my trip and battle other unforeseen problems that might pop up.


So here I sit behind my laptop now – there are a gazillion tabs that I have open in my browser, even as I type out this post. I trust in the fact that as time grows short and my options narrow, I will make it work, but right now I’m still doing quite a lot of planning and research, hmming and hawing my way through stuff.

The only thing I have firmly booked now is my round trip to Europe. Everything else is up in the air! Ack~ I’m also looking to run more errands – get some vaccinations done, as well as schedule in a quick trip or two before Japan if possible!

I’m also trying to be better about blogging and cleaning up the blog now I have a bit more time. But also to work on some freelance writing assignments which will help fund the travels. My honeymoon week is done, time to get down to stuff.

Added Later: curious about how my Career Break trip panned out? Here’s everything you wanted to know about how I planned and documented my 15 months of travel. I actually ended up planning a lot less towards the later part of my trip!

Read more trip planning advice if you are just starting to plan your own trips, or check out all my Career Break 2016-2017 posts and learn more about how I like to travel.