Wellbeing / Work styles

Do working holidays work?

I’ve previously written about a copywriter who’d take extended working holidays where he’d write each day from 5am to 12pm before joining his family for lunch and sightseeing. But can it really be done?


Rather than busting your gut for two weeks of pure holiday, could you stretch your trip length and budget by spending a section of the day working and the rest in holiday mode?

I’m lucky enough to be able to take my work with me, and having long toyed with this idea I finally got to test the theory on a short working holiday to a friend’s home in Lyttelton, New Zealand.

Day one was a bus and train to the airport. I managed 1½ hours of inbox clearing on the smartphone. The bus seats were a little cramped for my laptop, which had no web connection because I’m lacking in the dongle department, sadly.

I’d hoped to do more at the airport but by the time I went through check-in and customs, got a coffee and found the gate, I only had an hour of clear work time. And in spite of sitting under a poster advertising ‘free wireless’, I couldn’t connect.

In the end I had to call my colleague to talk through the website edits that I had planned to email. Then it was time to board. A cracking episode of ‘Modern Family’ and a power nap delayed my productivity, but I did get some solid work done on the flight, gloriously uninterrupted by web and email. By the end of workday one, I calculated three to four hours of sporadic work time.

"I think the dream of an extended working holiday is still alive and well. A farmhouse in Italy would do very nicely!"

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The next day we settled into my friend’s home office and were, surprisingly, very productive all day. We managed a walk at lunch time and I had the privilege of paying about $5 to pick up two voicemails. My friend has an outrageously cheap Skype service for all calls so that would be the go for future trips.

As I write this we’re clocking off for a weekend trek, and Monday will be another travel day.

The verdict so far: I’ve actually got a lot more work done than I’d expected, and it is great to be able to spend quality time with friends in their natural environment over several days.

Overall, I think the dream of an extended working holiday is still alive and well. A farmhouse in Italy would do very nicely!

I’d love to hear your views on the merit (or otherwise) of working holidays, and more generally on tips for combining work and travel. Wherever you are, leave a comment.

Peter Crocker

looks after content at Flying Solo. As part of Business Copywriter he partners with digital agencies and corporate clients on websites and digital content. He's the co-author of Flying Solo Revisited: How to go it alone in business.


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