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Should You Take a Working Vacation?

5 Questions to Ask When Considering a Working Vacation

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If you can work from home, then it's likely you can work during your vacation or holidays. But just because you can take a working vacation doesn't necessarily mean you should. People who work at home (as well as those that don't) should weigh the pros and cons of taking a working vacation carefully.

Ask Yourself These Questions About a Working Vacation


The considerations are a little different for those who are self-employed versus those who have jobs with paid vacation. But all should do a little self-assessment before we pack up our laptops for vacation.

So as you plan your family vacation or the holiday season, do a little soul searching about what you and your family want out of this vacation and whether you should need to take a working vacation.

1). Do you need to work on vacation?

If you don't work at all, will things back at the office fall apart without you? If so, what strategies can you employ (working ahead, finding a replacement, etc.) to prevent that from happening? And could better time management all year prevent problems at vacation time?

For many self-employed folks, there is no one else to watch the shop while they vacation. And so a a working vacation is necessary. Some may choose only do a limited amount of work while others more, especially if the choice is between a working vacation and no vacation. But don't let self-employment be an excuse for overworking.

2). How will it affect your family?

Remember this isn't just your vacation. Your working vacation can mean more work for your spouse and less fun for the kids. Similar to your work-at-home ground rules, spelling out how much and when you'll work can minimize family resentment. If you're trying to slip in a little work here and there, it may seem to the others that you're always working. Instead set aside a specific time and let the family know when you will and won't be working.

3). How difficult will it be?

If working means spending your days at an Internet café, when everyone else is at the beach, it may not be worth it. But if you can take care of a few things while everyone is sleeping or handle things by phone, working on vacation may be a viable option.

4). How much will you work on vacation?

If you decide to work on vacation, be careful that work doesn't creep in and take over. Don't leave it to chance; decide in advance how much you will work. And then stick to your plan as much as possible. On the other hand, if there is work-related task you must accomplish while on vacation, make a plan for when you will do it or you might not get to it.

5). What is the benefit versus the cost?

This is really where the soul searching comes in. Does the benefit that your company or business receives from your working vacation outweigh the benefit you and your family get from a vacation? And what is it costing you in terms of lost fun and family time?

If there some special reason to work--a project is due or your department is short-handed--is this really a "special" reason or do these type of things reoccur frequently? Could better scheduling of your vacation head off these problems in the future?
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