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15 Comments // Filed in Business / Etc

Working Holidays

Is it an oxymoron to go on a “working holiday”?

I’ve been feeling restless recently, and am wondering how many people have taken working holidays — and how successful are they? There are a few people who go off for weeks, even months at a time, to an exotic location armed with their cell phone and trusty laptop to work. If it’s so easy, why aren’t more people doing so?

In this day and age, where online business is all about efficiently working long distance, do we even need a fixed address any more? As a business person and a client — what do you feel are the benefits and drawbacks of working nomadically?

And yes, after my trip to Toronto/Montreal/Waterloo — this is at the forefront of my mind. I’m considering taking a “working holiday” in San Francisco for a month in the fall (I have friends, family, and clients in the Bay area). Thoughts?

15 blabs to Working Holidays

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As you know I’m doing the same in Illinois while searching for a job. I think they could work well but theres the problem of can you keep yourself working when you should and exploreing when you should? If so then I think its a good idea. Get you nice and relaxed and flowing with inspiration.

What do you mean? Every day is a working holiday!

I did it from Argentina once. Set up a Skype account and international calling on the cell. Wasn’t exactly easy, but fun and doable… But it kinda took away from total relaxation.

Picture of Lea

Name Lea

Date Jun 14
07:55 PM

Zach: Yes, that’s why I think if I choose a working holiday in a place I’ve already had a real holiday like San Fran, then I wouldn’t feel the need to explore more than if I had never been there.

Natalie: :-D Excellent way to look at things.

John:: How long did you stay in Argentina? Wherever you bring work relaxation is sacrificed. “Real” holidays can be equally exhausting if you go out every evening and do things every single day (which is what most people do as they usually only have a week or two to enjoy a place).

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Name reese

Date Jun 14
08:05 PM

as we talked about, I think it’s a fantastic idea. It could help a lot with creativity and inspiration.

I figure if we’ve chosen this path to work for ourselves from our homes, etc. we should really take advantage of it and see the world while we can. We’re both in the fortunate position of being able to take our work wherever we go. Hurrah!

If I could do working holidays, I would certainly jump on the chance. Sure, you’re not really on “vacation” per se, but you get to see new places and people when you’re not doing work (which should still be a decent portion of the day). So forget that “holiday” part and just go enjoy a new experience.

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Name J0sh

Date Jun 15
10:41 PM

I don’t know but – sometimes I do feel more relaxed while working in a holiday environment, ideas flow right of ya. Or so I have the feeling sometimes. Sometimes on holidays I can’t stop thinking of projects so I smack it into the Laptop or down on paper and end up working on it.

But alas, a working holiday does sound strange.

I was in Argentina for 6 months. It was great! Learned the language, learned so much about the culture, and made many friends.

Eventually I scheduled time for work on off days, when most of my friends were working or when it was raining.

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Name rico

Date Jun 19
10:43 AM

saffa de cudo el pasa!

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Name Nalan

Date Jul 07
07:37 PM

I’ve just discovered your website and only wanted to say “hello”!

Also, it is difficult to work without settled down for some people. However, I prefer a job on holiday. :)

Picture of elina

Name elina

Date Jul 10
02:20 PM

A great idea! And you always have a home with us – if you’re interested.

I’m constantly working during the holidays. You can’t really take time off with startup businesses.

I don’t think it’s any oxymoron at all… and I can totally relate to the added freedom the working ‘nomadically’. I’m a freelance designer and I very rarely work at home ? feeling that I get much more done and have much more creative-flow when I’m out in the hustle-and-bustle of England, and previously Los Angeles.

I find a “working holiday” is only has anything to do with working if I go by myself. It seems anyone else I go with, regardless of if I inform them that I do need to get work done (which pays for the trip) they end up getting frusterated if I don’t join an activity with them.

Not that I blame them, I think you just have to be careful of everyones expectations if it is more than just you involved.

I have never taken a working holiday, but think it is a great idea. I do take working breaks. I mean, if I get stuck on a project, I will actually change my physical location. A coffee shop, a book store. I have a couple places that I especially like. It is wonderful to have a “home base” for powering through designs and maintaining consistency; however, when I really need to think differently about something, sometimes the only way I can do it is by taking myself out of my element.

Good luck with the decision.

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