I went on vacation and didn’t tell my boss (shhh…)

Man relaxing on beach chair looking at the ocean


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Last month, I took a trip to the great state of Texas. It might not seem quite as sexy as the beach paradise in the photo above, but for me, it was exciting in a different way: I didn’t tell my boss.

Yup, you read that right. I went to Dallas for five days and gorged on barbecue, went sightseeing, shopped, and enjoyed some time with a few friends. 


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So how did I get away with it? Just a few years ago, a sneaky getaway on work time was considered a big no-no.

But as we all know, the pandemic changed everything. Think of a time you worked from home and snuck in an extended lunch break or went to the grocery store during your normal work hours. Let’s be real herewe’ve all done it. And there’s a very simple reason why:

Because working from home has blurred the boundaries between our professional and personal lives. And that’s given rise to a new way to travel.

They call it the workcation. And before you rip me apart, hear me out.


Vacations are changing

Once upon a time, workers lived for their two weeks off per year. People planned vacations months in advance and looked forward to them all year. 

My trip to Dallas certainly wasn’t a vacation in the traditional sense. In fact, it was more like an extended weekend getaway, but with my work mixed in. And trips like mine are becoming a travel trend.

“Mondays and Tuesday are the fastest-growing days of the week for travel. More people are treating ordinary weekends like long holiday weekends. This is also part of the flexibility afforded by remote work.

Brian Chesky, CEO of Airbnb

In my case, I flew out to Dallas on Saturday and back home on Wednesday laptop in tow. I worked my usual hours, attended every video meeting on my schedule, and got all my work done.

After work, my travel buddies and I went out for Tex-Mex, wine nights, relaxed in our Airbnb, and just enjoyed each other’s company. Oh yeah, they’re all full-time remote workers too.

This brings me to my conundrum. Considering that all my work was done each day and every meeting attended, it’s as if I worked from home. Still, I can’t seem to shake a creeping feeling of guilt. Was this ethical? Should I feel bad for having kept this secret? I think the answer depends on how you approach remote work.


Reasons why this makes sense

One of the greatest challenges of remote work is determining where work ends and your personal life begins. Indeed, one of the great debates is how much of a right managers have to know what you’re doing with your time.

If your gut instinct is that taking off on a getaway during work time is wrong, hear me out.

We’re working more than ever

The erasure of boundaries between work and life typically works in employers’ favor. Remote employees work an extra 1.4 days each month—and we’re so productive, it’s like we work an extra day each and every week. 

With all that hard work, finding a way to make the most of my after-hours downtime and enjoy a change of scenery (tactics for reducing burnout, I might add), without dipping into work hours, seems like a win for everyone.

Great managers don’t micromanage

When bosses micromanage and peer over employees’ shoulders, it sends a message that they don’t trust their workers. This undermines workplace autonomy and erodes trust. 

In fact, high performance often comes from giving employees independence and trusting them to get their work done on their terms. 

Great companies provide flexibility

I wouldn’t publish this if my company didn’t stand behind me. I’m a firm believer that if you’re a vital part of your team (as every reader here is), you’re entitled to your boundaries.

For example, here at RingCentral, we trust that our colleagues have their priorities straight. It doesn’t matter where they are or what hours they work. What matters is that they all play a huge part in the teams that they’re in. I’m proud that our executive leadership feels the same.


How to make workcations work

Every workplace is different, so it’s important to know what you’re dealing with before you skip town. For many, taking a workcation may require more transparency than my trip did.

And whether or not your team knows you’re away, it’s a good idea to follow these best practices for making workcations work.

1. Confirm you’ll have good connectivity before you book

From document sharing to video conferences, an internet connection is one of the most basic and essential requirements for working remotely. Conversely, without fast internet, it may be impossible to get your work done.

That’s why if the plan is to both work and play, don’t leave connectivity to chance. Confirm internet availability and speed before you book accommodations so you’ll know you can get online whenever you need to.

2. Be clear on availability 

Waiting for a teammate to get back to you with an answer to a question or their share of a group project can leave you in limbo and unable to do your work. You can prevent such frustrations for your colleagues, and keep work flowing while you’re gone, by clearly communicating your availability in advance. 

Looping coworkers into your schedule means they’ll know what to expect from you and allows them to plan—and can also reduce questions and contacts during your off hours when you’re trying to enjoy the destination.

3. Don’t hide that you’re away

When everyone is heads-down working, going AFK is something that we’re all guilty of. Maybe it’s an extended lunch break or signing off a few hours early.

But don’t try to hide that you’re traveling. Time zone differences can really muddy your schedule, and leave teammates wondering why you’re not responding.

Be upfront about your locations. Assuming your team is understanding and supportive (as they should be), you’ll have no problems continuing your work as if you never left home.

4. Keep your commitments

The only thing more annoying than an unreliable coworker who doesn’t do what they said they would is a coworker who promised to do something and is MIA on vacation. Indeed, the key to workcation goodwill is delivering on everything you said you would.

5. Set (and stick to) boundaries 

That said, the point of a workcation is to enjoy some recharging time—and you can’t do that if you’re tied to your laptop or phone the whole time. 

That’s why it’s also important to honor your commitment to yourself by setting boundaries—such as shutting down at a specific time at the end of the day, or going out for lunch—so you can make the most of your time away.

Originally published Mar 10, 2022, updated Jan 18, 2023

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