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Everything you wanted to know about my Career Break travels

So if you’ve been following The Occasional Traveller since 2016, you’ll know that it’s been a rather unusual year for me. Instead of balancing work and travel like I normally do with a full time job, I quit my job in February 2016 to embark on a long-awaited plan to travel extensively for a year, also known as my Career Break year.

Tokyo Asakusa Temple Selfie
MARCH 2016 – My first selfie in Tokyo – it’s not the first trip that I would take since I left my job, but I consider this the first day of this epic Career Break year when I started travelling with the intent of long term travel. Little did I know what was up ahead! This is me at the famous Asakusa Temple with the tourists the day before my birthday.

Well, at least the plan was for a year. Officially I was supposed to be back home end March in time for my birthday and to catch Coldplay in concert, but I spent my birthday flying over the Nazca lines in Peru and I hadn’t even made it to Machu Picchu and the Uyuni Salt Flats at that point, so I wasn’t quite ready to head home, just yet.

Istanbul Bosphorus River Cruise Selfie
MAY 2017 – 15 months later, one of my last selfies taken in my last destination Istanbul. I’m cruising down the Bosphorus River in the evening watching the sunset. You’ll notice that I’m wearing the same scarf as before, I’m still in a Uniqlo jacket, but that’s sunglasses #6 in 15 months because South America is just jinxed when it comes to me and shades!

In early June 2017 – I touched down in Singapore’s Changi Airport with no real plans to travel anywhere for a bit. Career Break 2016-2017 was officially done and dusted.

I kept pretty detailed records on my career break travels so I could look back and see how I might have done it better. But you know what, good or bad, I wouldn’t change any of it just because this was all part of my crazy experience. I hope this blog post helps anyone planning their own career break whether practically or inspirationally, but always remember – you do you. Go where you want to go, do what you want to do and don’t do what doesn’t make you happy, spend as much as you can afford and just travel your way, all the time.

Pin it: Everything you want to know about my Career Break travels in 2016-2017

Here’s a look at an interview I did with the Business Times about my travels in February 2017 – it doesn’t quite cover my entire Career Break but it gives you a quick overall sense of my journey up to that point. Also check out this interview by

Where did I go on my career break?

Career Break 2016-2017 Flight Map
All the flights I took in 2016 (orange) and 2017 (red) – apparently I clocked 57 flights in total, covering a distance of just under 160,000km and about 240 hours of flight time. We haven’t even started talking about those super long bus and train rides yet! All data taken from MyFlightRadar24 (Spasiba D for telling me about this cool website!)

So in total, I travelled for about 16 months from February 2016  to May 2017. I didn’t travel continuously though – I wanted to try long term travel but I knew that being on the road for too long would tire me out as well. I definitely got better at it along the way though – at the 7 week mark in my Asia Leg I was all ready to go home, but, 5 months in to the South America Leg and I felt like I could probably have gone on a little longer if I wanted to.

In summary:

  • I visited 37 countries in total over 5 continents – a big part of that is because I covered a lot of countries in Europe (20!) even though I might only have visited one city in those countries
  • 23 countries were new to me (Those places marked with * indicate new countries or new cities) – now my total country count is 54 which is still pretty mindboggling to me
  • I spent 350 nights sleeping in a foreign bed – most of which were in shared hostel dorms. I think I know a little something about hostel living and picking out the right hostels now~

Here’s a more detailed look at the places I visited during those 16 months – I listed countries as well as the major cities that I slept in for the night.

Japan & Taiwan

7 weeks / ~2 months

Career Break Map Asia Leg scribble
I was going to put up good clean maps but you know what, this was a lot more fun :)

I spent 7 weeks travelling in Japan and Taiwan – 4 weeks in the former and 3 weeks in the latter. I actually cut short my Taiwan trip a little because even though it’s one of my favourite countries, I was going at a really quick pace and I hadn’t quite gotten used to long term travel yet, so I got tired towards the end and was actually relieved to get home for a bit.

My journey started in Tokyo, cut across central Chugoku region towards Hiroshima and Fukuoka, and then across the sea to Okinawa. From there I flew to Taipei and then went clockwise around the island, ending my Taiwan journey in Taichung and flew home from Taipei.

Japan –  Tokyo, Takamatsu*, Shodoshima*, Naoshima*, Kurashiki*,  Onomichi*, Matsuyama* Hiroshima*, Fukuoka*, Okinawa*

Taiwan – Taipei, Yilan*, Taitung*, Lyudao, Lanyu*, Kaohsiung*, Kenting, Tainan*, Taichung*

Kurashiki River Swan Sakura
The Sakura season was a definite highlight for me!

Some highlights:

Eastern Europe + Kenya

15 weeks / ~4 months

Career Break Map Europe Leg scribble
I covered a looooot of ground in Europe! Most of it in the Eastern European region

I bought my round trip ticket way in advanced so I had a fixed timeline of about 4 months from June to September 2016 to explore Europe, with London as my chosen base to fly in and out off. The pros: knowing the parameters of my trip, saving some money by booking early. On the other hand, it meant having to make plans around my fixed dates and flights which were not always the most convenient – my last destination was actually Berlin but I had to fly back to London because that was where my return ticket was from.

I flew into London to visit friends and attend a friend’s wedding, popped over to Zurich to visit another friend, and embarked on the great Balkan escapade over a lovely summer starting from Slovenia. After 2 weeks in Croatia and realising I didn’t actually have that much time for the entire Balkan region, I headed northwards after Dubrovnik towards the Baltic states until I hit Tallinn in Estonia. Then I flew to Amsterdam (just because I’d always wanted to see it), took a detour to Kenya and back to Berlin (also just because), before heading back to Heathrow and an insane dash to the airport to catch my flight home, phew!

United KingdomLondon, Manchester, Liverpool


Slovenia* – Ljubljana, Karst, Bled

Croatia* – Rovinj, Porej, Rijeka, Zadar, Split, Hvar, Vis, Dubrovnik

Bosnia & Herzegovina*Mostar, Sarajevo, Konjic

Serbia* – Belgrade, Novi Sad

Hungary* – Budapest

Slovakia* – Bratislava

Austria* – Vienna

Czech Republic – Brno*

Poland*Krakow, Wroclaw, Lodz, Gdansk, Warsaw

Lithuania* – Vilnius

Latvia* – Riga

Estonia* – Tallinn

Netherlands* – Amsterdam

Kenya*Nairobi, Mombasa

Germany – Berlin*, Gottingen*

Kenya Diani Beach Skydive View
Look at that amazing view! My first time skydiving and it was a doozy!

Some highlights:

Latin America

22 weeks / 5.5 months

Career Break South America Leg Full scribble
The longest leg of my Career Break is called the South America Leg but I actually covered 4 different continents over this period!

I had about 3 months at home to ‘rest’ before I embarked on this leg, but I actually spent a lot of it doing smaller trips around the Asian region (more on that in the next section), so I was still travelling pretty extensively even though I was technically at home. I also was procrastinating a little bit because I couldn’t decide whether to spend Christmas and New Year’s at home with family and friends or to get off my ass and start travelling again. South America was a completely unknown entity to me, and I was honestly a bit nervous about it, which is why I think I sat on my decision for awhile.

I had some accommodation to check out in South Korea so that’s where I headed first, and then up to Vancouver to ski and spend time with a friend. I figured out my South American flight and spent New Year’s Eve in the air, starting 2017 in Bogota, Colombia. From there I made my way down Colombia through Ecuador, and took a detour to Panama for a Spanish Language collaboration, before continuing my journey in Peru, circling down to San Pedro de Atacama in Chile, going up through Uyuni in Bolivia, and then heading back into Peru and ending my South American journey in Cusco. I flew to Spain for some downtime en route to Bucharest for a travel blogger conference, and then went through Bulgaria and finally ending up in Istanbul, turkey. Finally I flew home, ending my South American leg and my Career Break journey properly in early June 2017.

South KoreaSeoul, Gwangju*

Canada – Vancouver

Colombia* – Bogota, Medellin, San Andres, Cartagena, Santa Marta, Palomino, Cali, Ipiales

Ecuador* – Quito, Latacunga, Banos, Cuenca, Guaayquil, Galapagos Islands

Panama* – Bocas del Toro, Boquete, Panama City

Peru* – Lima, Huacachina, Nazca, Arequipa, Tacna, Puno, Cusco

Chile* – Arica, San Pedro de Atacama

Bolivia* – Uyuni, La Paz, Copacabana

Spain – Madrid, Valencia*


Bulgaria* – Sofia, Veliko Tarnovo, Plovdiv


Peru Machu Picchu Llama Photobomb
I had a llama photobomb me while taking pix of the ruins in Machu Picchu and good lordy this pic went viral on Lonely Planet’s instagram garnering almost 30,000 likes!!

Some Highlights:

Other Trips: South-East Asia and USA

Career Break Map Others scribble
Most of my little trips were around Asia, with the exception of San Francisco

I took some smaller trips in between the major legs when I was back in Singapore, mostly media/FAM trip opportunities that I would not have been able to undertake in the past because of my full time working life, but now I could finally take them! Most of these were around the South East Asian region, but there was also the epic San Francisco trip which saw me take a 16-hour non-stop flight, make a 12 hour pitstop at home, and then head to the airport for another 12-hour non-stop flight to London. Now that was an insane time~


IndonesiaSouth Sumatra*, Bali, Flores*

United StatesSan Francisco*

ThailandBangkok, Amphawa*

Laos*Vientiane, Luang Prabang

Philippines – Manila*, Anilao*, Coron*

Komodo Padar Beaches V
Probably one of my favourite pix taken on Padar Island while exploring Flores and Komodo islands with Skyscanner!

How did I plan my career break?

Pre Trip

Career Break - Home Blogging
Most of my planning took place on my computer! This view hasn’t changed much since I returned haha

Honestly – I didn’t have much of a plan because I wanted to give myself more flexibility, which is something you don’t get as much of when you are only travelling occasionally. You kinda want to maximise a 2-week holiday or a long weekend as much as possible, but I didn’t want to be locked into a schedule for an entire 4 months.

So if you are looking for me to give you some sort of magic formula to planning long term travels… tough luck, you’re gonna have to make do with what I actually did for tips :P

Where to go

I started out with a very broad idea of things I wanted to do:

  • Europe and South America were on my list of regions I wanted to explore more of now that I had more time
  • I wanted to visit new countries and new cities mostly, not so much places I’d been before. Preferably I wanted to head to areas less popular among Singaporean travellers
  • Catching up with overseas friends was also quite high on my priority list as well

A lot of other random factors influenced my final itinerary as well, mostly from opportunities arising from the blog or just other cool things happening that I wanted to be a part off:

  • Japan was largely due to me getting the JapanTravel photojournalism internship which helped me save a little bit. A big push was also the chance to see the blooming Sakuras in season
  • London was my base to fly in and out of Europe because I had a friend’s wedding to attend and tickets to the new Harry Potter play, and it’s a major hub for flying within Europe and back to Singapore
  • Zurich was purely to visit friends, as was skiing in Vancouver
  • Kenya was a total detour when the chance to join my friend Helen’s inaugural small tours came up after I had bought my London flights. It was a bit of a YOLO decision, but I definitely don’t regret it even though it meant I was zooming through 3 Baltic states in a week to spend 2 weeks in Kenya. I highly recommend her both as a friend and tour leader over at Rock My Adventure
London Harry Potter Play Me
Everything came together for London! I scored preview tix to the play and honestly you never run out of things to do in London

But there is some essential stuff that I definitely recommend doing pre-trip:


Some people have said that getting vaccinations is cheaper on the road than in their home countries, but I like the certainty and reliability of Singapore’s healthcare system. I went to Tan Tock Seng Travellers Clinic to get recommendations on what jabs I needed, but also to my local GP down the block just because it was more convenient (even if it did cost more). What I ended up getting:

  • Flu
  • Typhoid
  • Tetanus
  • Hep A & Hep B
  • Yellow Fever (this one comes with a cert, you may need it for certain countries in South America but I never had to pull mine out)

Overseas Credit and ATM Cards

Because I was going to be visiting so many countries over an extended period of time, and not all the places I was visiting were credit-card friendly, I decided that my main source of currency was going to be via the ATM. The main thing I needed to figure out was which banks would charge the least or no fees for foreign bank cards.

  • Many ATMs charge you an extra fee on top of what your home bank charges you – I was using Citibank at first because they don’t charge you that home fee, but I busted my card somehow and had to use my backup UOB card which charge me SGD5 every time I took out money on top of what the foreign bank charged me. Pretty sure I racked up a lot of unnecessary charges here!. If anyone from Singapore has a recommendation on an ATM card that doesn’t charge you extra, I’d love to know which one!
  • Some banks have arrangements with certain foreign banks to not charge additional fees. The only downfall then is having to hunt down those particular banks when you want to use them.

Travel Insurance

Travel Insurance is a MUST for me – you can read more about why. You honestly never know when you’ll need insurance but I highly recommend you protect yourself. Travel Insurance came in especially handy on this trip. Some things I had to claim for:

  • Partial claims for my stolen iPhone in Budapest – I bought a new phone in the suburbs of Budapest and while I couldn’t claim the full amount, any small bit does help
  • Medical fees for when I fell sick and lost my voice in Krakow

Typically because I tend to travel quite suddenly, I have an annual plan, but the catch is that there is a 90-day out of country limit so I technically wasn’t covered for some bits of my 4 months Europe Leg because I was out of the country for more than 90-days consecutively! (You need to go back to Singapore to ‘reset’ the 90-days)

For South America, I took precautions and bought additional WorldNomads [affiliate link] to cover the weeks beyond the 90-day limit because unlike most plans, you don’t need to be in your home country to purchase it. It is more expensive though! Other people I know have flown back home and out again to get around that clause, but I wasn’t going to do that all the way from South America. An alternative that you can check out is Safety Wing [affiliate link] which is built for travel nomads.

During the Trip

Career Break Budget Google Sheet
My master Google Sheet that I used to keep track of expenses on the go – as you can see I’m a very visual person! I used it more to keep a record of how much I spent than an actual budget tracker to limit myself on per day spending.

I had some essential tools that helped keep me organised on the go. Actually I don’t think I’ve ever been so organised when it comes to travel in terms of recording my budget and travel details! It came in really handy when I was working on budget posts or just trying to remember where I was on a particular day and what I did.

Itinerary & Budgets

Google Sheets – I had a master sheet which recorded everywhere I stayed, how much I spent and the flights I took. It was also pretty useful for itinerary planning on the go, especially when I started running short on time and wanted to figure out how long I could spend in a particularly place. These days, I use Trello to help with my trip planning because I like the way you can move things around.

Trail Wallet – I started out managing my budget on Google Sheets as well but it was such a hassle formatting for different currencies, so I bit the bullet and paid for the Trail Wallet app for the South American leg and I think it was an excellent decision because it saved me so much effort. It’s really easy to use on the go and visual, and does automatic conversions into my home currency so I definitely recommend it highly. Only for iOS users though.

Currency – I used my ATM card to withdraw cash mostly, and had little ziploc bags with labels to help keep my currency separate. I had SO MANY different currencies from all the different countries that I visited that it was essential to keep it all separately! I’m a big wallet type girl at home who carries every thing in one giant wallet, but on the road I usually used a tiny purse that I can stash deep in pockets and had a card phone case that I held on tight to.

Flores Kelimutu Casio FR100
This is how I took all my jumpshots and anything in the water – with my trusty FR100 – the screen (remote) in hand while the camera (the round bit) perched on the floor. Accidentally killing it in the Galapagos was heartbreaking, and I’m kinda bummed I didn’t have it for Peru and Bolivia!

Photography & Tech Gear

iPhone 6s – this was super essential as my main info source, note taker, translator, communication device and camera. The day I had my phone stolen in Budapest was an extremely upsetting one – I went straight out the next day after making the police report to buy a new phone in suburban Budapest, an expensive but essential thing I just had to do. I actually used my phone for writing blog posts when I didn’t want to bother fishing out my laptop, and I also developed an e-book habit on Kobo and read on my phone on long transits

Casio Exilim FR100 – this was my outdoor waterproof camera that I brought along for anything from canyoning to snorkelling, or even just went it started to rain. I really liked it but was sad to accidentally get water in it after the Galapagos. Thankfully it’s fixed now!

Surface Pro 3 – I needed to do some writing work and blogging on the go, so I brought along my Surface Pro 3 because it is lighter than the Macbook Pro I normally use at home. I like that it’s touch screen as well. This hybrid tablet-laptop is little pricey so the fear of losing it was pretty high. I think I disguised it pretty well in my laptop case which looks like an airmail envelope [amazon affiliate link].

Buffalo External HDD – I use this to back up essential documents and photos, and also because I needed a lot of my archives for freelance writing and blogging on the go, and there wasn’t enough space for all my photos in my Surface. I highly recommend this one with built in USB wires [amazon affiliate link] because you don’t have to worry about wires and it really is hardy – I’ve had mine for YEARS.

Xiaomi portable battery – I lost my original one in London on a rather drunken evening, so I had to make do with a back up throughout Europe, but this is definitely an essential given how much I use my phone, and all my friends recommended it and I can see why. The 10,000maH Xiaomi Portable Charger [amazon affiliate link] charges your phone very quickly and can go about 4-5x before it needs to be recharged

Dropbox [referral link] – I synced my phone photos to my computer as soon as I had wifi (sometimes shitty in places), and used it to transfer info between my computer and and used a Buffalo external HDD to back those up and keep my dropbox and camera from getting too full. I also carried an extra microSD card and thumbdrives just in case.

Instagram was my most updated social media platform that I used to chronicle my journey – I created a unique personal hashtag for each country that I visited which made it easy for me to pull out photos of places to recommend people when I didn’t want to dig through my entire photo archive

Booking Apps

For accommodation: [affiliate link] was my go-to in most places, followed by Hostelworld when I wanted to verify prices or reviews or find more ‘typical’ hostel type places. AirBnB was for when the cheap hotels and hostels in a place just proved unsatisfactory. I usually booked accommodation for the next place when I knew how I was going to get there or my transport had already been fixed. That ranged anywhere from a few days in advance to on the afternoon in the city itself when I found a wifi spot

For transport: there isn’t one main platform I used, it usually depended on the country, and quite often I’d just turn up in the bus or train station and get my ticket directly. That said, I loved Polskibus in Poland and used a lot of Cruz del Sur buses in Peru. You’ll also be surprised how many countries get Uber, though it is of varying popularity. Bogota, Medellin and Lima were surprising spots for Uber for me and great for airport transfers, and I used it a fair bit in Bucharest as well

For flights: I use Skyscanner for a sense of pricing and who’s flying where, and if I can I go direct to the airline website  because I’ve not had good experiences booking from 3rd parties when I run into trouble! That said, I hate Vivacolombia’s website and it hates me in return too. I couldn’t book with my Singapore credit card and even when I used someone else’s card, I still ran into problems. SIGH.

iPhone Main Screen Apps
Here’s a look at what my main screen looks like – essentials like Units Plus, Trail Wallet, and Kobo are easy to access!

Other Travel Essentials – for offline maps. Download the area map when you are on wifi to prep for a new place. You can download certain areas for offline use with Google Maps if you prefer. Usually is pretty decent but I’ve run into times where it’s hard to find specific places because its not always as detailed as Google Maps. Also you need specific map apps for some countries – Naver map in Korea, or Baidu Maps for China are better than Google.

Units Plus – for converting currency easily. It’s pretty easy to use though I wish you could type sometimes instead of endless scrolling

Google Translate for simple translations – download the full language pack when you are on wifi to prep for a new place and so you can use it offline as well. It’s not always the most accurate but it’s better than nothing. Translate short words instead of long phrases for more accuracy.

Memrise – for learning a new language. Some prefer Duolingo, but I think I like the Memrise interface better

SIM Cards – I usually prefer a portable wifi device which I used in Taiwan and Japan thanks to Changi Recommends. But a SIM card is easier if you are hopping through a lot of different countries like I was. I usually got a SIM if I knew I was going to spend more than a week in one country. Countries I bought SIM Cards in: Hungary, Poland (this remains my favourite SIM card ever – 10GB of data for 5 zloty/SGD 2!), Ecuador, Panama, Peru, Romania.

I also used something called Flexiroam [referral link] which is a sticker you can attach to your original SIM card that lets you use data in many countries without having to swap your SIM card out. If you are going to be travelling very quickly and have no time to shop, and hate having to swap out your SIM card, consider this instead. What I didn’t like was having to constantly restart my phone to switch between the profiles (the original profile and the Flexiroam profile) and that the data isn’t particularly cheap – you’re paying for convenience basically!

How to pack

I knew I wanted to streamline and go as light as possible – I’d never packed for such a long term trip before! I opted for the 44L CabinZero backpack which I had been carrying for long weekend trips since 2015.

Career Break CabinZero Military Japan
All packed for Japan and Taiwan! I definitely packed too much that first leg, and learned to pack lighter for the subsequent legs

Backpacking forces you to become an expert packer because you will spend your entire trip packing and unpacking – soon you’ll know every item in your bag intimately as there is a ‘fixed spot’ for each item to ensure optimal space, you learn to consider how much you really want to buy a particular souvenir as well. I’ll probably do a more comprehensive packing post someday, but here are some tips I picked up.

I had to mail myself stuff 3 times in total from Japan, Taiwan and Panama, and I had to get an extra duffel bag in Madrid because I had way too many souvenirs and bulky alpaca stuff from my time in South America, but I definitely enjoyed not carrying around too much on the whole. Here’s the detailed review of the CabinZero if anyone is interested.

Essential Packing Tips

  • Packing cubes are the best thing to maximise space. My cubes were always super full because I was intent on squeezing out as much space as I could
  • I generally prefer to roll rather than fold, but sometimes you just have to be creative in squeezing stuff between crevices or layering
  • How you pack is as important as what you pack. Sometimes just turning things around or combining different items frees up unexpected room. Packing a full backpack is like a game of tetris which takes awhile to get the hang of, but soon you’ll know exactly which items can be manipulated for more room
  • Your bag shouldn’t be full right at the beginning of your journey – that’s what I did for the Japan-Taiwan Leg and I had to mail myself stuff back 2x. For Europe I was only 3/4 full at the start so that was much better managed
  • If you have squeezed till you can squeeze no more but still need to pack everything into a bag for check in, what I do beyond wearing my thickest clothing and bulkiest shoes is to tie my outer jackets onto my carry on bag, or wear them if I have to. I’m like a walking Christmas tree~
Career Break Packing Top View
This is what it generally looks like when I’m trying to pack – I’m at home here but you can imagine I definitely don’t have as much space in a typical hostel room, so that’s when tote bags and being organised about your bag comes in very handy

How much to pack

I packed clothes to last me for about 7-10 days without doing any laundry. I basically used my underwear as a gauge – with 10 pairs, I started looking around for laundry options when I was about 2/3 way through. The Europe leg was much easier to pack for because it was purely summer gear with some light jackets thrown in, while South America leg was tough because I had to carry bulky winter jackets around and that the climates there are so extreme, from hot humid desert to freezing snowy mountain tops – thin Uniqlo heattech layers are a life saver!

That also meant that I was doing laundry quite frequently on the go which is something I’d never done before, here are some of my tips:

Laundry tips

Don’t wait till you are completely out of clean clothes to do your laundry– sometimes the laundry process takes longer than expected and you really don’t want to be stuck in your one set of clothing for 2 days straight. I usually start looking for laundry options at about the 70% usage mark, did laundry around every 10-14 days.

Laundry options on the go:

  • Laundry machines in hostels that you pay to use – I usually make sure I promptly remove the clothes once they are done so that other people don’t move my clothes and mix things up in my pile. An important thing to look for is making sure your hostel also has a dryer machine, especially if you are pressed for time as you don’t want to be packing damp clothes into your backpack (eww)
  • Laundry services where you give the hostel or the laundromat your dirty clothes and they come back clean – the feeling of wearing freshly pressed clothing is awesome. Pick a time when you are going to be staying in one place for a bit so you aren’t freaking out if your laundry gets delayed (it happens) and you need to catch a flight the next morning

You’ve hit the laundry jackpot when your accommodation offers FREE LAUNDRY SERVICES (First Hotel Taipei and Morning Glory Hostel [ affiliate link] in Puerto Ayora for the win!)

I think you should bring clothes that you are comfortable wearing multiple times on a long term trip, but I would leave the very precious, delicate and easily wrinkled stuff back home because sometimes stuff does go missing, or you get a stray red sock that stains everything, and you don’t want that to ruin your trip.

Consider handwashing the smaller items like socks or bra padding which tend to get lost more easily – in my entire journey I only lost one bikini bra pad (do you know how annoying it is to have to constantly shift 3 bra pads between 2 bikinis? It’s extremely annoying), but there were always lots of stray socks lying around the laundry area.

Quick dry stuff is also another godsend, especially when your hostel doesn’t have a dryer.

Jac Changi Airport Departures
This is the classic version of the CabinZero (I own the 3 different versions) – I carried this to San Francisco, came home and switched bags before zooming off on my Europe leg

Packing essentials for hostel living

Empty tote bags and smaller bags – good for separating clean and dirty laundry, and also for sorting out your things in hostel rooms when you need to take all the stuff out of your backpack but don’t want to leave it around randomly.

A clothesline – for hanging up and airing your clothes in bunk beds. Can just be a piece of rope that you can repurpose, but it helps to have a few clothes pegs on hand as well.

Locks and spare locks – I carried around 6 locks with me in South America. I thought I was being paranoid, but I lost 3 locks mostly in Peru so it turned out to be a good move after all. I prefer number locks but I had key ones as backups, as well as a larger bike lock for chaining my backpack down when there weren’t lockers and I wanted to be extra careful

Tape – washi tape is good for scrap booking and keeping small objects like SIM cards and SD cards from disappearing, but some duct tape is good to as it is more durable

SIM card pin or paperclip – when you swap SIMs a lot, this is super useful to have and more sturdy than a earring wire. I usually stick mine to the inside of my phone case or wallet so it’s easy to pull out when needed

Large thin scarf – good for hot and cold weather, filtering out terrible smelling buses, hanging up for extra privacy in dorm beds or just prettying up a casual outfir for a night out

Shoes – I carried 3 pairs of shoes:

  • 1 pair of runners/hiking shoes that I wore everywhere. I liked the low cut Timberlands because they are sturdy enough for hiking, and you don’t get made to take them off at some airports because they are not boots
  • A dressier fold-up pair of ballet flats for nicer nights which is also space saving- I have the blue and pewter Yosi Samra from Just Tangy
  • A pair of flipflops – I’d pay more for something hardy and thicker than your super cheap throwaway pair. Mine lasted an entire year of hardwearing

How much did I spend?

Bolivia Uyuni Salt Flats Back Poncho
Ka-ching! Uyuni was not the cheapest thing but completely worth the money, to me at least!

The question most people are curious about – how much did my Career Break cost? I’m not going to give you an exact breakdown of my expenditure because I don’t think people travel in the same way at all so it’s not really relevant to see the complete breakdown. Also, some of my numbers are also skewed by the fact that I do get sponsored travel opportunities from the blog so take that in consideration when looking at my figures.

In total I spent about S$45,000 – that works out to about S$2,800 per month, which is just under S$100 per day on average. This includes all my costs from transport, accommodation, food, souvenirs… everything I spent on the road and some stuff in preparation for the trip.

Is that considered a lot? I’ve had varying reactions but I think it really depends on your style of travel and how much you are willing to spend. It’s definitely not budget but neither do I think is it super extravagant. If you want budget options, why not check out my friends Sunrise Odyssey who managed to do Central Asia in 10 months for around S$10,000 or Pohtecktoes who did about 2.5 months in South America for less than S$7,000.

My plan was either to travel for a year or until my money ran out, whichever happened first, but I knew I didn’t want to be a flat-broke begpacker before I came back, so I decided to stop once I felt that my savings were running too low for my liking

Want to see a slightly more detailed breakdown?

Breakdown of expenditure

Career Break Expenditure Breakdown

Sights – This cost the most because it included the small tours I did like the 3D2N to Uyuni Salt Falts, 2D1N to Machu Picchu and of course the expensive 8D7N Galapagos Cruise. It also includes expensive stuff like scuba diving (I did several dives in different countries) and the skydive I did in Kenya! Definitely could be reduced if I had been more judicious about what I spent on.

Flights – the best way to save is to not move around so much like I did! And also not to take too many detours – Kenya was a detour that I bought pretty last minute, as was Panama. This figure would actually have been much higher (I mean I took 57 flights – this averages out to about $150/flight which is just ridiculous) but I had some flights covered by media trips, as well as a handful of discounts from friends who worked in the airline industry. I paid for slightly over half my flights, an average of around $280/flight. Miles users will surely save a ton in this category!

Food – I ate out mostly so I probably could have saved a lot here if I cooked, but I like eating out, it’s part of appreciating the culture for me! My average food cost was about $20/day – I had a mix of street food and some fancy places

Accommodation – I was mostly doing shared hostel dorms, but I generally didn’t pick the cheapest hostels available – quality and location are pretty key factors for me. Cheapest countries I stayed in? Bulgaria, Istanbul, Bosnia & Herzegovina, Serbia, Bolivia. I had some sponsored accommodation, stayed with friends and sometimes had to fork out for an expensive hotel room, but my average cost for a bed per night came up to about S$20. You could definitely push this down if you couchsurfed, bunked with friends or picked hostels based on price

Transport – we’re mostly talking trains and buses here. Again like with flights, less moving around would mean more savings in this category.

Souvenirs – I definitely could have saved in this area as well, I spent a quarter of that money in Japan and Taiwan right at the beginning, but was much more judicious in Europe. I bought a fair bit of souvenirs from South America but mostly for the family. My coolest souvenir would probably be the Alpaca-wool poncho from Ecuador. The most useful one would be the notabag I bought in a museum shop in Vienna and actually carry around a lot nowadays.

Misc – these extra costs were largely due to the travel insurance and vaccinations as well as the Tourist Tax/Visa I needed to get for Galapagos and Bolivia.

Colombia Cartagena Jumpshot
A few days before this shot – I’m panicking about having to completely overhaul my Skylife article about Singapore at the last minute. Some sleepless transits later, I actually manage to turn out something decent on time

How I funded my Career Break

I talked a bit about how I was funding my travels when I announced that I quit my job, but now that I’ve actually gone through with it, I can give you a bit of a lowdown:

My Savings – this took the hardest hit because for the first time in my life I was seeing money go out of my account faster than it came back in. It honestly was a bit worrying seeing the money in my account deplete but you know what, totally worth it. I didn’t deplete my savings though – I came back with a decent amount left to cover my expenses for a few months while I figured out life and job hunting.

Freelance work – I took up a lot more writing jobs on the go, and I think I was pretty lucky in landing some jobs that just came to me randomly. In total I made about $17,000 from freelance work and sponsored blog posts in 16 months, which covered about 1/3 of my expenditure.

Sponsored stuff – I didn’t use my blog as much as I could have because I didn’t want to get tied down to too many commitments while travelling – let me just say that when it looks like I get something for ‘free’, you’re not seeing the work I put in behind the scenes, the long nights and some missed opportunities when I have to get shit done and can’t go out because of deadlines, so I tried to keep it minimal. But things like the opportunity to learn Spanish in Panama was pretty awesome, as well as the chance to explore Bucharest even if it meant having to take some detours and extra flight costs!

Post Trip – Now what?

Changi Airport Welcome Back Jun2017
An insta story of me at the airport after flying back from Istanbul, 5.5 months after I left for Seoul on my South American leg

I’ve been back in Singapore for almost 2 months now at the point I’m writing this, and I’ve been absolutely busy. I started job hunting and have had a few interviews so far though nothing’s quite landed yet. I had listed my blog and Career Break in my professional resume for the first time and the response has been pretty good so far – it’s a great talking point and according to one of my interviewees, having ‘passion projects’ was a plus point in my favour. I honestly wasn’t expecting to even land interviews so early, but I’ve been lucky to have a strong network of supportive friends who were happy to throw recommendations my way when I caught up with them.

For now I’ve taken up some freelance and contract work on the side to earn some cash while job hunting, and I am trying to catch up on blogging -– which is an entire job in itself. I could probably not travel for a few years and still have a ton to write about!

Update 2019: I’m back doing full-time work and being an Occasional Traveller 3 years since my Career Break and after about 2 years of freelancing. It was a matter of the right opportunity popping up at the right time :)

I definitely don’t regret taking this time off. I think the Career Break has shifted my mindset in terms of how I think about myself and my travels for the better. I’m a lot less willing to settle – which is a good and a bad thing, and I think I’ve definitely grown up a little more. Experiences on my travels have made some things clearer to me, that I don’t want to be a digital nomad nor make my blog my main source of income for example, and that perhaps I want to cast my net beyond Singapore shores and that full-time work in an office isn’t the only way to make a living.

If you are pondering taking the same step, let me just remind you – you do you. Don’t quit your job to travel just because it looks like I had a great time, do it because it’s something you want to experience or achieve. Everyone has their own journey and adventures in life, and I hope you have amazing ones whatever you decide! I’m happy to try and answer questions or even just hear about your own experiences if you took a career break too – just drop them in the comments or drop me an email if you prefer some privacy.

Catch up on all my Career Break Travel posts or see what tips I have for busy working professionals who want to indulge their love for travel.


Monday 23rd of October 2017

I read about your blog on Eng Beng's website, and just fell into a rabbit hole of reading your archives - so much good stuff. I went to South America for five months this year after quitting me job, and wished I took a whole year off like you did, instead of just a few months. Also wished I was more organised, like you, hah. Here's to more adventures!

Jaclynn Seah

Monday 23rd of October 2017

Thanks Yan Qin – Well 5 months is still a good amount of time and man your blog photos are making me miss South America so much! Cheers to more adventures for you and me and everyone :)


Tuesday 15th of August 2017

I am moving to singapore soon for work during Oct! cannot wait to come to this great country! :)

Jaclynn Seah

Wednesday 16th of August 2017

awesome! hope you like it here :)


Sunday 6th of August 2017

This is a nice comprehensive post.

I have only done two separate mini-breaks that last for 1 month each (first time covering 11 Scandinavia/Europe countries, second time covering the Middle East), and agree that such breaks wouldn't necessarily harm your career and is a good talking point in interviews.

Great to hear you caught the migration. I was a little too early for the migration while I was in Tanzania this year, but Africa safari is such a spectacular experience I just know I'll be back for more!

Envy your South America leg the most—that's one place I have always felt needed months if not years to do justice, so I haven't checked them out yet. Bolivia, Ecuador, Colombia & Atacama are all high on my wish list, but especially Patagonia in Southern Chile...

All the best for the job hunting. Pretty sure you'll land something very soon!

Jaclynn Seah

Sunday 6th of August 2017

Thanks Andrew! I have to admit I"m kinda raring to go again :p Thank you for the well wishes!

Scandinavia and the Middle East are places I haven't really covered properly! Definitely for next time... Scandinavia seemed a bit too expensive and I've heard some really cool things about Iran and its surroundings. Central Asia is also pretty high on my list :) There's also so much of Africa to see... man my list just keeps growing!

South America I do agree you need a little time to do, just because the country is so big and getting around takes time...