To Plan Or Not To Plan Your Career Break – 5 Factors

So you’re planning your career break… guidebooks, blog posts, forums and websites. All those years of seeing someone else’s photographs and thinking “I’ll go there one day,” and suddenly you might have the opportunity. So on the itinerary it goes, but if you’re not careful, then you’ve planned every day of your time away from your armchair.

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But life has a way of being unexpected, and besides, for a lot of us (well, me!), a careerbreak is about shaking things up a little, and my plans changed a lot.

1) Round the world or point-to-point airfare

Careerbreak version #1 involved hiking around Eastern Europe, before heading to South East Asia, having a wander about for 8 months or so, and then going to New Zealand via Japan. Not much planned, just move on as and when.

And then we saw the cost of the tickets.

As New Zealand was non-negotiable, the cost of the point-to-point tickets were astronomical, and we realised it was a lot cheaper – almost half the price! – to do a round the world plane ticket instead.

It’s not always more cost effective with a round the world, but once you start looking at Australia and New Zealand, and South America, it often is.

So Careerbreak version #2 was born, and suddenly we had fixed points: London – Rio de Janeiro; then Santiago – Auckland – Sydney – Bangkok; and finally Singapore – Helsinki – London, with most of our time spent in Asia.

That was the first concession we made to planning our time away. It wasn’t the last, but it was probably the most important as now we had a framework to build on.

All the bits in between – like getting from one side of South America to the other – we still made up as we went along, travelling mostly by bus but also by plane once we got to Asia and its plentiful budget airlines. It worked well as the round the world ticket stops were often quite far apart (e.g. there were nearly 8 months between the flight into Bangkok and the one out from Singapore) so we still had lots of manoeuvrability.

If I could have my time over, would I still pick a round the world ticket?

Maybe, maybe not. The penalties for changing it were quite harsh (a lot more than we were led to believe when we bought it), so we only altered one segment, but I’d have liked to re-route a few times. That said, it was a bargain (leaving more money for more places), and I got to go back to Australia and visit some new South American countries.

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2) Proof of onward travel


Most governments around the world just don’t like you arriving without some scheduled exit – especially flying in. There’s a lot written about this online, and I’m not going to re-hash it here, but just so you know, we had to prove onward travel at the following airports at check in. And we couldn’t often use our Round-The-World ticket as proof as the gaps between flights were too big. We were never asked for it at a land crossing or by immigration officials.

  • Auckland before flying to Sydney
  • Ho Chi Minh before flying to Manila
  • Manila before flying to Kota Kinabalu
  • Taipei before flying to Tokyo
  • Tokyo before flying to Busan
  • Seoul before flying to Kuala Lumpur

We were also asked for it in Sydney (quite aggressively too!) before our Bangkok flight, but we successfully argued that we didn’t need it as we had acquired visas. A lot more of the airlines we flew with could have asked for it but didn’t.

All of this meant that if we were flying in somewhere, then we normally knew when we’d be leaving, even if we didn’t quite know what we’d be doing in the intervening weeks!

3) Accommodation

Put away those visions of traipsing round guesthouses and hotels weighed down by your backpack looking for vacancies. It’s 2014, and there are online deals to be had!

I estimate we pre-booked 95? of our accommodation, but that doesn’t mean we lost flexibility – often it was only a day in advance, sometimes just a few hours.

In some countries – like Laos – it was cheaper to go around to guesthouses, but in a lot of countries, it wasn’t. And anyway is it really worth the hassle? Wandering from door to door with your backpack, looking needy and subsequently being subjected to outrageous rates far in excess of what was being offered online (Calafate, Argentina, was the worst for this, followed by just about every Thai island we visited. In several places they wanted 50% more than the price I was able to get online).

I’ve found this year that 9 times out of 10, it either cost the same – or less – to book online as it did to just show up. So we typically booked a night or two online first, and then if we liked it we’d stay longer and try to negotiate a discount. And several times – Malaysia and Korea were big on this – the receptionist would tell you to book the extra nights online as well or it would cost more.

In Sydney and Santiago, we also rented apartments, and needless to say they needed a bit more planning.

Finally, watch out for other people’s holidays – finding somewhere to stay in Thailand at New Year was the stuff of nightmares, as was generally doing anything in Indonesia over Eid!

4) Transport

The Philippines neatly sums this up. First off we got stung massively because we didn’t book our internal flights to Palawan far enough in advance at Easter – the cost literally doubled in two days. But once we got to El Nido we suddenly found all these modern speedboats running between there and Coron that weren’t in the guidebooks, and we needn’t have bought flights back at all!

The moral of the story? While most hotels and guesthouses now have some form of online presence, a lot of the bus and boat companies do not. Sometimes it pays to not have an exit strategy as you won’t be able to see what the connections are until you arrive.

5) Times when plans have to go out the window

Things will not work out quite as you planned, so there’s no point in being OCD when it comes to your itinerary.

In Brazil my tooth broke, meaning I ended up spending 9 days in Lima that I hadn’t foreseen getting a root canal and crown! In Bolivia I had chronic food poisoning and hightailed it for the Chilean border and more sanitary cooking methods. And then in Chile the ferry route into Patagonia ceased operations, so we were forced into an overland crossing into Argentina and then zigzagging back.

And then there was the flip side – properly being able to catch up with my friends in Lima and crossing into Argentina so early we found the utterly gorgeous Bariloche and its surrounding Lake District.

But the biggest itinerary change was in Asia. We grew tired of the backpacker trail of people in their late teens / early 20s with the same dreadlocks and the same ukeleles strumming out the same Jason Mraz song.. I actually thought we might come home early. So we overhauled our itinerary and went to Taiwan, Japan and Korea. And Japan is my new found favourite place. I adored it and can’t wait to return!

How it ended up

So from all those plans back in the UK, this ended up being my careerbreak around the planet.

UK – Brazil – Peru – Bolivia – Chile – Argentina – Chile (again!) – Argentina (again!) – Chile (yes, a third time!) – New Zealand – Australia – Thailand – Cambodia – Laos – Vietnam – Philippines – Malaysia (Borneo) – Taiwan – Japan – Korea – Malaysia (peninsular) – Indonesia – Singapore – Finland – Estonia – Finland – UK

Ever so slightly different from New Zealand and back via Romania! So plan your career break as much as you dare, just remember to leave some wriggle room and see where you end up…

Grant Winborn had always had a bit of a love affair with his backpack, but decided to properly go for it in 2013 when he quit his well paid job back in the UK and set off on a year-long careerbreak in South America, New Zealand and Asia (with a well-earned week-long party catching up with Aussie friends in Sydney whilst in the neighbourhood). Some may call it a mid life crisis – especially when he just happened to cross the Dateline fifteen minutes before his 40th birthday, missing that particular day entirely – but he just likes to call it an adventure. You can read his blog at Rice Bowls and Rucksacks or follow Grant on Twitter. 

Photo credits: I love photo, all other photos courtesy of the author and may not be used without permission.

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