How to Take a Working Vacation

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The working vacation sounds like the dream, and it very much can be, in many ways. What really makes the difference between a dream come true and a potential nightmare has everything to do with planning and preparation.

There are two ways to take a working vacation: Getting a job where you are going, or having a work situation which allows you to work online. Both have their unique challenges and we’re going to take a quick look at each situation.

Getting Jobs Abroad:

This option is better for the younger, more able, and maybe less connected (yet) in the business world among us. In fact, if you want to get a working holiday visa Australia, for example, you can’t be over 31 years of age.

If you’re going to go this route, make sure you follow the following simple advice:

-Don’t try and work under the able anywhere, no matter how little you think the laws are enforced over there. Especially don’t try this in Singapore. At a bare minimum you will be deported and barred from coming back for life. Secure the proper authorizations before you go.

-Most temporary work permits for foreigners are for industries in which a particular place tends to lack manpower. Be prepared for some pretty hard labor in harsh conditions, in many circumstances. Some visas, like the Australian visa mentioned above, require you to spend the working part of your time in rural areas.

–Watch your finances carefully, and understand the REAL cost of things like basic necessities where you are going. Try to get as much of them included in the contract, so that you can save while working in order to enjoy the free time you get after properly.

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Having An Online Job:

This is the ultimate dream for so many, as it allows you almost complete geographical freedom. This is still not paradise, though, not even in its best case scenario. There are a few caveats, to be aware of.

-Make absolutely sure that your internet connection is rock solid wherever you may be going.. Some countries have internet on a par with anywhere else on Earth, others have really amazing and cheap internet, others have pretty third or fourth rate internet service. Do your research beforehand.

-Make sure where you are staying affords you an appropriate degree of privacy and comfort and isolation so that you can get your work done properly. This especially applies for work that requires things like Skype calls and even more so if it requires frequent teleconferencing.

-Be prepared to have your jet lag compounded by having to work at some pretty strange hours due to time zone differences.

-If you are in the States, short term lodging can be incredibly expensive. One good way to get around this is with an RV rental. This also saves a lot of time checking in and out of hotel rooms etc.

-Above all, don’t plan on doing this for more than a year or two. This lifestyle is amazing but it’s surprisingly very lonely.

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Jeremy Kaplan

A 50-something year old lifestyle, career, and education blogger based in Atlanta, Georgia. Years of experience in the office setting working with others and still loving it year-after-year.

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