Objections to Expect

Objections to Expect

Objections workation

When you tell someone your plans to take a workation, there is (understandably) some skepticism. Here are some of the common objections or questions you can expect to hear:

  1. That’s a long flight to take with kids.
  2. Why would you travel with kids when they’re too young to remember it?
  3. You’ll never be able to keep doing workations once the kids start school.
  4. That must be really expensive.
  5. Your job’s ok with that?

So let’s take these one by one.

That’s a long flight to take with kids. Long flights can be tough, for sure. Our door-to-door travel time from our home in Minnesota to our apartment in Wellington, New Zealand was 32 hours. We had a 5 and a 3-year-old at the time. While on a plane, the biggest saving graces have been iPads and movies. We also bring along a few activity books and such, but honestly the variety that an iPad offers without having to haul a bunch of extra stuff on the plane makes it worth it.

We started going on workations when our youngest was 2-years-old – old enough to be moderately entertained by simple iPad games and movies while on a plane. I imagine it would be trickier if the child was much younger and couldn’t be as easily entertained. I’d love to hear tips from parents with infants!

Why travel with kids when they’re too young to remember it? I always think this one is a strange comment. Following this logic, why would you do anything with your kids if they weren’t going to remember it? Why read to them or play with them if they weren’t going to remember it? So we travel with them for the same reasons you’d do anything else with your child: To expose them to new ideas, new places, and to show them that different isn’t scary. And also, my husband and I don’t live for just our children! We’re both in our 30s, have decent income and are healthy. We’re going to travel now and not put it off until the kids are older or until some mythical retirement. If we can do it now, we’re going to do it now.

You’ll never to be able to keep doing this when the kids are in school. This may become a valid point as the kids get older and have required testing and/or start to play sports/extra curriculars. But who knows? We’ll cross that bridge when we come to it. For now, our oldest son is in first grade and when I told the principal our plans, he barely batted an eye. His response was, “Have fun!” Between the online learning options and emails with the teachers, I’m confident he won’t fall behind.

So if you have kids in school, talk with their teachers and principal and see what sort of timing may be a red flag from an educational standpoint. But maybe you have more flexibility than you realize! Does their teacher use an online learning tool like EPIC or RazKids or IXL that your child could access from anywhere? If you have older kids, does the teacher post homework online, and is something your child get or do overseas? If you have an older child, could they join you at a coworking space and do their school work while you are at your work day?

That must be really expensive. There are lots of trade-offs with workations that can help with the cost. Maybe you hire a nanny when you’re abroad, but you can avoid tuition or daycare costs back at home. You rent an apartment elsewhere, but you can rent our your home on AirBnb or to some friends. You cancel your cable while you’re away. You remove most of your car insurance. There are lots of ways to lower or eliminate your day-to-day costs are home and shift those expenses to your overseas life. For the flights, we use credit card points to lower the cost of tickets.

Your job’s ok with that? The answer to this question depends on the employer, your type of work and your relationship with your boss. I recommend broaching the subject early on and come with ideas about how you could make it work and value to your company while working from somewhere else. Tim Ferriss does a great job in the Four-Hour Work Week (“Step IV” section) of laying out specific language to use with your employer to convince her/him to let you work remotely. I’d recommend starting there.



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