Out Of PTO? Experts Reveal Dos And Don’ts For Successfully Working On Vacation

• When planning a vacation, whether you plan to use PTO or not, it is essential to let managers know.
• When employees are open about their work locations, it helps maintain clearer lines of communication with team members and managers, and limits surprises. 
• It’s important to set realistic expectations for what you can accomplish during your workation, and focus on the most important tasks.

As 2024 draws to a close, many employees are finding themselves in a bind — how can they manage a break later in the year when all their paid time off (PTO) is already gone? Or do they dare risk planning a quick vacation for their remaining day or two when it’s flu season and a sick day (for themselves or their kids) might come up? 

While many people do still work remotely, or have a hybrid arrangement that might make a long weekend possible, not everyone has the remote flexibility to work from a beach, a hotel, or a cruise ship. 

Some who do have that flexibility have turned to “quiet vacationing,” which emerged as a popular work trend this year, with many workers around the world seeing it as a practical solution for conserving their limited PTO while taking advantage of their ability to work remotely. 

Navigating gray areas between maintaining professionalism and personal time balance has definitely become more difficult as work models have shifted. Is it a good idea for an employee to keep their work location a secret from their boss? Does it matter if you’re working from an office in an Airbnb vs. your home? 

To address these types of questions, experts offer three do’s and three don’ts of working while on vacation.

First Things First: Yes, You Should Tell Your Boss

More and more hybrid professionals in 2024 have found themselves working remotely while on vacation — often without informing their employers. Still, business leaders like Mark Whitely, founder and CEO of Whits Services Corporation, recommend that as part of the vacation planning process, an employee should let their boss know they are planning a trip.

“Planning ahead means letting your boss and coworkers know you’ll be working remotely,” Mark Whitley, shared with Allwork.Space. “[B]eing free will prevent bad surprises in the future. I always ask my team at Whits Services to plan their holidays in advance. Not only does this help them enjoy their vacation stress-free, but it also ensures that everything runs smoothly at work while they are away.”

A study published by The Harris Poll reveals “the top barriers preventing workers from taking more time off are ‘pressure to always be available and responsive to demands’ (31%) and ‘heavy workload’ (30%).” 

These factors have largely contributed to 24% of Gen Z, 37% of Millennials, 24% of Gen X, and 18% of Boomers having already engaged in quiet vacationing this year.

Scott Lieberman, founder of Touchdown Money, shared three additional reasons with Allwork.Space on why employees should notify managers when vacationing.

First, it “reaffirms trust between you and the boss” while demonstrating respect for the job. 

Second, it “avoids any teamwork disruptions,” especially if “you are in a place with a different time zone or don’t have an optimum network connection to do your work.” 

Third, if management knows you’re traveling, they may be more flexible with response times and project deadlines.

The 3 Dos of Working on Vacation

1. Set Clear Boundaries

Many professionals, including Jim Chichanski, founder and Chief HR Officer at Flex HR, cite the importance of setting clear boundaries for handling emails and other work-related tasks when traveling and working.

“The reason most key employees like to be somewhat available [when using PTO] is they don’t enjoy coming back to work and there are 2,000 emails sitting in the inbox and possible wrong decisions made while they were gone,” Chichansky said. “Set your email response to let folks know you are out and have limited access to emails.”

Designating times to check in and manage work-related tasks are also recommended to help employees stay productive during a vacation or trip without letting it turn into another workweek.

By setting these clear boundaries, an employee can prevent work from overtaking a trip designed to lower stress and clear the mind. Workplace experts like Chichanski imply that employees don’t need to constantly check emails when both them and the employer know you’re supposed to be recharging. 

When on PTO, a focused 30 minutes, or an hour at most, is usually enough to handle any urgent matters and prevent things from piling up while professionals are away from the computer. This approach helps employees stay somewhat available while still preserving time to relax — making the return to work go much smoother.

2. Communicate with Team Members

When employees are open about their work locations, it helps maintain clearer lines of communication with team members and managers. This is absolutely essential to avoiding any potential misunderstandings or concerns raised while traveling.

Whitley recommends full transparency when working remotely on vacation, or when asking for PTO. The openness helps build trust and allows teams to adjust expectations if someone is not fully available.

“We live in a world where communication is easier,” Whitley said. “Use technology to your advantage when trying to balance work and vacation. Set up automatic responses to your emails, address urgent issues with a colleague, and use project management tools to keep everything on track. Cloud-based applications for video conferencing and file sharing mean you can still join meetings and access important documents wherever you are.”

Team members who are made aware of work arrangements for the week can offer support in handling time-sensitive tasks. It also allows them to plan ahead and distribute responsibilities for the days when remote work and traveling is planned. 

The key to successful vacationing while working is to make sure communications are accessible to team members so that no one is left in the dark on what to do and when to do it.

3. Prioritize Mental Health and Well-Being

If using PTO, Chichanski recommends taking 3-4 days to recharge without the stress of falling too far behind at work. 

“A short break, even for a few days, can do wonders for your mental health and productivity,” says Chichanski. “You don’t need a long vacation to feel refreshed, but you do need time where you’re fully disconnected.”

During these brief vacations, Chichanski suggests providing an alternate contact for emergencies to ensure that important matters are handled while you’re away.

By managing expectations and letting people know you’re unavailable, you can truly switch off and return to work feeling more focused and energized. This approach helps maintain a healthy work-life balance and gives you the opportunity to fully unwind, knowing that you’ve prepared your team for your absence.

The 3 Don’ts of Working on Vacation

1. Don’t Try to Maintain a “Normal” Work Schedule

“In my opinion, one of the biggest mistakes people make is trying to replicate their regular work schedule while on vacation,” Stephen Greet, CEO and Co-founder of BeamJobs said to Allwork.Space.

Greet warns that this approach often leads to frustration and burnout because it creates unrealistic expectations about productivity. It also leads individuals to feel like they haven’t truly taken a break. As a result, this can offset the positive benefits of vacation, increasing stress levels in the long run.

“Instead, I think it’s important to acknowledge that your availability and productivity will naturally shift,” Greet said. “Focus on flexibility — set a realistic work plan that accommodates both your need to relax and your professional duties.”

This can start with an employee changing their mindset to accept that productivity may look different while on vacation, and that’s perfectly fine. Greet suggests setting realistic goals that balance work and time to disconnect. 

“Maybe that means working early mornings or late evenings and dedicating midday to enjoying your surroundings,” said Greet. 

The key here is flexibility. An employee who allows themselves time to work during low-stress periods, while also setting aside time to unwind, can avoid burnout and actually enjoy their time away.

2. Don’t Overcommit On Large Projects While Traveling

As Whitley points out, overloading your vacation schedule with large work tasks defeats the purpose of taking time off in the first place. 

It’s important to set realistic expectations for what you can accomplish during your workation, and focus on the most important tasks. Much like Greet, Whitley explains that overextending what can be done while traveling can leave you more stressed and tired than before.

This also ties into the fact that keeping your vacation plans a secret could backfire. Being fully transparent helps manage expectations and avoids issues if things go wrong. Experts recommend that if an employee expects connectivity or time zone changes to affect your work, to not hold that a secret.

“I’ve seen people come back from ‘vacation’ more tired than before they left because they worked too much,” said Whitley. “It’s not cheap. Know your limits and stick to them.”

Instead, focus on the most important tasks that need to be handled during your trip and let go of the rest — at least until returning to a normal work schedule. Trying to accomplish everything can lead to over-exertion. Employees can prioritize their well-being by setting boundaries on how much work they commit to projects, ensuring that they are not constantly on call during much-needed off time. This will allow the employee to feel more refreshed, productive, and ready to handle your responsibilities when returning to a regular work environment.

3. Don’t Neglect Your Actual PTO

Quiet vacationing — where you work while on vacation — can be a helpful solution for balancing professional and personal responsibilities. However, it should never fully replace actual time off. 

Several experts agree that using PTO to completely disconnect is vital to maintaining long-term productivity and mental health.

Jim Chichanski, founder and Chief HR Officer at Flex HR, stresses the importance of taking real paid time off after working during a vacation. 

“If you end up working during your vacation, be open with your boss about it and request time off later to fully disconnect,” said Chichanski. Being transparent about when you worked during vacation also allows an employee to negotiate for proper time to recharge later. 

The fact that quiet vacationing has become a practical solution for managing shrinking PTO and heavier workloads underscores the need for companies to re-evaluate their PTO policies in ways that promote employee well-being.

Encouraging genuine time off, even for employees who work during vacations, can help sustain long-term productivity and prevent burnout in today’s fast-paced, always-connected work environment.

Employees who set clear boundaries, communicate with their team, and prioritize mental well-being, can enjoy time off without sacrificing job security or mental health.