The Stress of Disconnect: To Work — or Not — on Vacation

by Jennifer Sigler | June 22, 2017 | Workhappy Blog

Sandy beaches, sunglasses and email – the cornerstones of today’s vacation.

Working happy is our jam. We love to hear stories from people who love their jobs and love the companies they work for. We also love to give a shout out to employers and companies who offer comprehensive benefits packages and other office perks that make doing the job at hand more enjoyable.

But sometimes, working happy requires us to take a break from working entirely. I am talking about the almighty, ever-elusive vacation.

It is essential to attempt to escape “the grid,” to decompress from feeling on-call all the time. If you follow us regularly, you might have noticed content has slowed down in the last few weeks. This is, in part, because I took a much-needed vacation.

My career is currently made up in equal measure of freelance writing and finishing my dissertation. And I love it.

But this means disconnecting is easier said than done. For me, there is no one to delegate work to — other than to decline it, which means a slimmer pay check.

You know what I’m talking about if you are an entrepreneur or an independent consultant. You may need to stay connected so that client needs are met, or to stay on top of any issues; there simply may not be someone else to take the helm while you R & R. Even when you are granted a certain number of paid vacation days per year, if you hold a key role, you may be expected to check-in frequently.

And while there are many good reasons not to work on vacation (it’s healthier, it’s part of your benefits package, i.e. part of your compensation, etc.), to disconnect completely is a luxury of which many of us feel we cannot indulge. Guilt, worry, and financial strain all contribute to “the working vacation.”

At times this distress of disconnect stops people from taking a break at all. In fact, according to Expedia’s 2016 Vacation Deprivation Study, American workers failed to use approximately 375 million paid vacation days within the last year.

  1. Million.

Maybe the answer is not to disconnect — not completely. While I wouldn’t consider myself in any way a “workaholic,” (even though I do work very hard, and love what I do) I find myself a proponent — at least, in part, if only by design — of the working vacation.

Here are three things I learned from my recent holiday:


As much as you can. Get ahead on current projects so you can be better prepared for the deadlines you will face upon your return. This may require some very long days — but it is better than the alternative: Pulling very long days (that often creep into the night) when you get back.

Also communicate your plans with any relevant clients. Establish that you may not be as responsive as usual — and let them know when you will be back in “go mode.” You should also establish your plan for communications or any work you plan to get done during vacation with your superiors.


Vacation travesty that it is, sometimes it is just impossible not to do a little work on holiday. But remember, you are on VACATION. Checking your email a dozen times a day or cracking open the laptop whenever you hit a Wi-fi spot not only stresses you out, but disrupts those you are with.

Decide a time to check in daily, do it once, and then leave it alone. It is easy to get sucked into emptying your inbox, but resist the urge and respond only to what needs immediate attention.

However, if a project does requires immediate action, by all means, take care of it. Vacation is all about allowing your mind and body to relax — which you won’t do if you are preoccupied by urgent business.  You need to set limits based on your own comfort level. But by setting limits, and compartmentalizing your time, you can work while on vacation without disrupting the vacation part of your vacation.


Plans are great and all, but sometimes (read: a lot of times) plans don’t happen the way they were engineered. Sometimes, you plan on having Internet access, only to discover it is spotty, or being worked on or being replaced.

Communicate any hitches that come up, and then figure out your next step. If you have something that absolutely cannot wait until you return, this might mean finding a coffee shop or co-working space to quickly grind out some work.  This might also mean, “let it go,” and put it in the “I will deal with it when I get back” column.

Remember, anything that must get done should be unplanned. If you go into vacation knowing there is a time-sensitive project that will require your attention, you’ve picked the wrong time to take a vacation.

Some of these points I learned through practice over my recent holiday, while others have only come with the clarity of hindsight.

While hopefully it is possible to get away at some point without “checking in,” the reality is much more complex. But this doesn’t mean we can’t take steps to make the process as easy and pleasurable as possible. After all, isn’t it better to take a vacation and work a little if the alternative is never taking a vacation?

Jennifer Sigler is a Senior Writer with The UpWrite Group. Send a message to to see how she can help enhance your corporate or personal brand.

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