Home Thinking Aloud The Working Vacation Is Making A Comeback. Here’s How To Do It...

The Working Vacation Is Making A Comeback. Here’s How To Do It Right.


by Rick Grimaldi, author of “FLEX: A Leader’s Guide to Staying Nimble and Mastering Transformative Change in the American Workplace

Across America, folks are packing their beach bags, their hiking boots… and their laptops. Maybe you’re one of them. The kids are gearing up for school and you’re ready to seize those last few weeks of togetherness. Or your company is bringing everyone back to the office this fall and you want a “last hurrah.” Either way, you’re going on vacation and taking work with you — so how to make the most of it?

If you find yourself confused about how best to navigate this strange hybrid of business and pleasure, you’re not alone.

Working vacations, as they used to be called, have always been the norm for successful people. But moving forward, this arrangement will apply to more and more of the workforce. And learning how to manage it can be tricky.

Part of the reason for so many working vacations is the pace and intensity of business: very few of us can totally unplug for two weeks at a time anymore. To a degree, work responsibilities will creep in. But it’s also a natural outcome of a larger trend toward work/life integration.

This trend isn’t a bad thing because it’s enabling flexibility. Yes, work is spilling into personal lives, but also the reverse is true. It’s great that employees are feeling more and more empowered to set their own hours, work from home offices at least part of the time, and better accommodate their family’s needs.

That said, people do need real down time. Burnout is a huge issue right now. You have to make the “vacation” part of the work/vacation hybrid really count or you’ll come back to work frustrated, tired, and resentful.

Vacation is a state of mind. Switching from one world to the other can be challenging. For example, you might get bad news on a work call, and then have trouble moving back into the vacation mindset. It can be tough to present with your family when your mind is at the office.

A few tips for doing working vacations better:

Rather than straddling both worlds all day, plan to work in big chunks of time.

For example, block off mornings from 7:00 to 10:00 to work. Then, when that time block ends, shut down the computer and put the phone away.

What typically happens is that people spend the day looking at email on their phones and they never really disengage. Tech has been a double-edged sword for that.

Draw some hard lines…

Having ill-defined boundaries is where people go wrong. They try to do both things at once and end up doing neither of them well.

… But also know when to break the boundary.

There are exceptions to every rule, and there will always be work emergencies or client calls that can’t wait. This is when you may need to get creative to meet the needs of both work and family.

Once, years ago, I was on a family vacation in Puerto Rico. I convinced my daughter she would have fun hiking up a mountain with me (which she did) but, in part, it was a ruse so I could get cell reception for a call! We both had fun, I handled business, and it became the stuff of family legend.

Leaders, establish cultural rules inside your company that respect employees’ time.

There should be an unwritten rule that you reach out to someone on vacation only if there’s no other option. When everyone respects everyone else’s time and space, you’ve gone a long way toward creating a culture that attracts and retains the best talent.

When you learn to manage this process well, it can be an incredible experience. On the other hand, if you don’t, it can be a disaster both professionally and personally.

Being able to flex and work around a family schedule can be quite useful. It takes the right mindset, a little advance planning, and some clear communication to mix business and leisure time — but it can be done and done well.


Rick Grimaldi is a workplace trends expert and the author of “FLEX: A Leader’s Guide to Staying Nimble and Mastering Transformative Change in the American Workplace“. Day to day, Rick works with companies to help them adapt to the ever-changing business environment, achieve their workplace goals, and become better employers. Rick is an internationally recognized writer and keynote speaker.



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