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Are Workcations a Good Idea or a Trap? How to Take a Workcation

What are workcations? Do they count as time off when you aren't really disconnecting?

The word workcation is a portmanteau of work and vacation, but is it really either of those things? 
A "workcation" is a vacation during which an employee continues to work. As a result, an employee can hold onto their PTO, if they have any left. 
But what does it really mean to work on vacation? Is workcation really just remote work by a different name? Is there a way to balance the leisure of vacation with the hustle of work?
One thing we know is that employees appreciate this substitute for the traditional vacation. In 2022, Passport Photo Online surveyed 1000 workers about workcation—and they were on board the S.S. Workcation Trend.
86 percent of respondents “agree” or “strongly agree” that a workcation boosted their productivity. 69% are less likely to quit their job after taking a workation.
In this article, we'll explore this new trend, the pros of working on vacation, the cons of removing boundaries between your on and off time, whether workcation suits your life, and how to plan a workcation. 

What Is a Workcation?

Before workcation, there was bleisure. A combination of “business” and “leisure," this term was coined back in 2009.
Four years later, Wall Street Journal Bestselling Author of Captivate & Cues Vanessa Van Edwards introduced the idea of workcation, as she and her husband embarked on a new career adventure combining uninterrupted travel and career development. 
Workcation, as we described, combines the words "work" and "vacation." If it sounds like an oxymoron to you, you're not alone. 
For some of us, vacation is a break from work. It's a time to set boundaries with our OOO replies, to disconnect from work, to spend time with our loved ones (or in quiet, blissful solitude), and to recharge our mental health. 
When work is added to this relaxation soup, doesn't it throw the whole idea of vacation out of the window? What kind of beach getaway includes Slack notifications, Zoom meetings, and email?
On the other hand, if rejiggering your vacation or destination wedding weekend into a working vacation makes more frequent travel possible, maybe that's not such a bad thing! 

Why People Take Workcations

There are a few reasons employees take workcations instead of vacations. Some employees simply don't have PTO (boo to their employers!) so they remain on the clock from the beach out of necessity. 
Sometimes, folks combine a long wedding weekend with a workcation to extend time away without dipping into their PTO.
Employees might turn a work trip into a workcation by extending their visit for a few days. When you think about the gratis business class flight and comped resort stay, this type of workcation doesn't seem half bad! 
However, there are other reasons employees take workcations that are less situational and more...organizational. For example, many organizations offer "unlimited PTO," but is any employee really taking the "unlimited" days off without fearing for their job stability? 
Some employees feel wary about taking any PTO. They fear missing out on an important meeting or opportunity. Other employees, especially when working at smaller organizations or startups, might lack support. As a result, workcation becomes necessary without a substitute in line to allow for an actual vacation. 

The Benefits of Taking Workcations

The success of a relaxing workcation hinges on two big things: flexibility and a reliable internet connection. 
If your boss is the type that likes to keep tabs on your status and activity, your workcation is going to be decidedly less enjoyable. However, if you work a flexible schedule and your supervisors trust that you can handle your own work-life balance on your own, you can bury your phone in the sand for an hour or two. Now, that's a workcation! 
Employees love workcations. The same study from Passport Photos Online found that 83% of surveyed employees agree or strongly agree that a workcation helped them cope with burnout.
In busy seasons or tough quarters, our vacation days are tempting to take, but the timing isn't always right. Sometimes, a workcation is the perfect cross-section between work and leisure. It can be the perfect antidote to workplace burnout
The same study found that workcations help to boost creativity at work. 81% of respondents said that a workcation helped them become more creative.
We all know that a change of scenery can do wonders in altering our perspective and helping us to think differently. When a full-fledged family vacation is out of reach, a workcation to Miami might help an employee to break through and achieve a professional "Aha moment" finally!

The Cons of Taking Workcations

Okay, workcations are seeming pretty great. 
Who wouldn't want to wind down from their last meeting while waiting for a virgin pina colada to arrive at their hotel door? Who doesn't want to close their laptop and jump right into a clear, blue pool?
We cannot discuss workcations—the blend of leisure and professional—without addressing boundaries. 
In fact, boundaries are one of the trickiest problems in the remote work fight. How do we separate our home office from our home? When does your dedicated workspace turn back into your bedroom closet?
There are two specific boundaries we want to address here: 
  • The workcation versus vacation boundary
  • The delineation between "we" time and "me" time on a workcation 
The first boundary is the workcation versus vacation boundary. Specifically, this describes a scenario in which an employee sets the expectation that they will work on their downtime.
When these employees take a real, work-free vacation, their supervisors don't know how to respect the actual time off. 
In these circumstances, it's crucial to communicate when you expect to take paid time off versus times when you're open to engaging in some bleisure. 
This employee can overcommunicate their availability (if any) in an email to their supervisor and colleagues beforehand. In addition to that email, an employee should also set clear expectations with a boundary-building OOO message

How to Take a Workcation

Requesting a workcation is not too much different than requesting other vacation time or PTO. 
Pro Tip: If you have a supervisor who isn't keen on flexible work, this might be a key moment. Prepare to request your workcation while leaving little room for your boss to ask questions or gain clarity. Anticipate everything! 

1. Plan Ahead

Determine the dates for your workcation. Consider factors such as project deadlines, workload, and any important meetings or events.
Choose a time when your absence will have the least impact on your team and clients. Avoid big project completion dates, heavy meeting days, or other instances when you know your presence in the office is lucrative. 

2. Outline Your Plan + Address Any Potential Concerns

Prepare a detailed plan that demonstrates how you will manage your work during the workcation. This plan should include:
  • Your availability and working hours while on the workcation.
  • Specific tasks and projects you will focus on during this time.
  • How you'll handle communication and collaboration with your team, including a colleague to sit in for you when necessary. 
  • A clear understanding of how you will meet your deadlines and work responsibilities.

3. Discuss With Your Boss 

Initiate a conversation with your supervisor or manager to discuss the idea of a workcation. Schedule a meeting or have an open discussion about your intentions and how it can benefit you and the company.
If you do this right, it could be the beginning of more flexible work for you and maybe even your colleagues.

Workcation Request Email Template

The time has come to request your workcation. Start daydreaming about digging your feet in the sand and working on your analytics report while getting some sunshine—a nice respite from sitting under harsh fluorescent lighting. 
The following template includes space to provide the context and expectations around your work during your workcation. While it does not include details about where you are going or why, you may share this information at your discretion. 
Subject: Request for Working Vacation Approval

Dear [BOSS'S NAME],

I am requesting your approval for a working vacation from [START DATE] to [END DATE]. This arrangement will allow me to balance my need for relaxation and work responsibilities effectively.

During this time, I am committed to maintaining productivity and ensuring my absence does not disrupt the team's workflow. I have already taken some measures to prepare for my temporary absence, which include:

1. Informing my colleagues and team members about my upcoming vacation and ensuring they have the necessary information and resources to cover my tasks in my absence. [EMPLOYEE NAME] has agreed to cover my in-office duties while I am out of the physical office, and we have agreed to keep in close contact. 
2. Setting up an out-of-office message with contact information for an alternate point of contact, if any urgent issues arise.
3. Ensuring all deadlines and deliverables are completed or rescheduled accordingly to avoid inconveniences for our clients and projects.


Taking this working vacation is essential for me to recharge, reduce stress, and return to work with renewed energy and focus.

Thank you for considering my request. Please let me know when we can discuss this further, or if you require any additional information to decide.


Best regards,

[NAME]

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