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Planning A Working Vacation? 5 Things You NEED to Know

A working vacation isn’t the same as a real vacation. Keep these 5 things in mind as you plan your trip.

Not all remote work positions will allow you to take advantage of a work vacation.  But some certainly do.  If you were to embark on such a trip- there would have to be essential things in place to insure not only appropriate workflow, but also appropriate work/family separation so that you can do your job. 

Here’s 5 essential things to know as you plan your trip.

1. Family Buy-In

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Don’t just assume that everyone in your family would want to go to Hawaii for a month or rent a San Diego beach house for 6 weeks. If I have learned anything being married it’s that you don’t assume ANYTHING. 

There needs to be lots of communication about this. 

What would the kids do in such a place? 

Who is watching them? 

Will they be in camps in those places? 

How would they keep busy for those weeks in a new place? 

Take your spouse into consideration as well. Who would they see? What would their community be like away from home?

These are essential talks and parameters to talk about before making any solid plans

2. Location, location, location

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This might be difficult as almost anyone would love to have a 5-story beach house for the summer, but can you really afford it? 

Would you be able to afford only a 2-bedroom condo inland from the beach in a less than desirable area?

Would that that really be a great trip for your kids or you?  Would you even be able to get work done there. 

So overall there must be adequate space for everyone to live and work. Keep that in mind as you search for your site.

3. Cost

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4 weeks in Hawaii would be amazing but can you really afford that keep our mortgage going in your home state? 

What about food? 

Do you eat mostly at home, or do you eat out more? 

A detailed budget with clear plans for expenses is crucial here. You want this to be both enjoyable and affordable.

4. Adequate Time For Work and Play

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As part of the planning process insuring everyone knows the work/home rules- so that when working the work can be done and one can remain employed. 

This is where having a plan for the kids, and for the person not working is really essential.

5. Finding the “Why” for your trip

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Why take a working vacation like this? 

Is it to expose the kids to a new area or opportunity they don’t have in your home state or city? 

Is it to see extended family for a longer period of time? 

Is it to fullfill a dream of living somewhere new and testing the waters in a new place? 

Finding the “why” for your trip that everyone can agree on can make it easier to make planning decisions and to remain levelheaded when things don’t always go as planned.


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