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The Do's and Don’ts of a Great Workcation: Tips for Employees


Simon Vreeswijk

Director of Marketing - 30 Aug, 2022


If you follow our blog, you know we are big fans of the “Workcation”. We’ve shared a lot of expert tips about how to ask to take a workcation, and how to make sure it’s productive. How can you make sure that your workcation is a great one - for not only you, but your employer? Remember that the better this experience is from your management’s perspective, the more likely they will be to let you (and others in your organization) take a workcation again.

Here we are sharing our top tips for what to do and what not to do when it comes to a successful workcation.

Refresher: What’s a Workcation?

A workcation is a working vacation. On workcation, you take a break from the workplace, but not the work itself. In this type of situation, you go where you please, but do so while working remotely. You may also hear of this referred to as “bleisure”, a combination of business and leisure.

If you already work remotely, you may have some experience with a workcation and the benefits the arrangement can offer. For example, maybe you’ve visited family for the holidays or accompanied a spouse on an out-of-town conference, and took your laptop with you. If you are normally in a traditional office, though, then a workcation is probably new territory for you.

The pandemic revealed several new trends in the working world, with more remote work being one of them. More employers than ever before are amenable to workcations and other less traditional working arrangements. Research shows that most Americans (67%) agree with taking a workcation to “recharge their mental and emotional batteries”, and 94% plan to go on a workcation again in 2022 and beyond.

Why Take a Workcation?

This type of arrangement is becoming more popular, as employees pursue work-life harmony and more employers embrace flexibility. There are a number of reasons why people love workcations, from the very obvious to the indirect.

As for employers, the benefit of offering workcations is that they help them to attract and retain the best talent. With the pandemic came many new forms of working, and people have come to value the flexibility that comes with remote working. Most organizations are aware - in ways that they weren’t before - of just how valuable remote working arrangements can be to their best staff.

Here are some of the top benefits that come with a working vacation. 

  • You save time (and can actually be more productive). Mirroring one of the great benefits of remote work in general, workcations allow you to skip the commute. They may also allow you to save the time you’d normally spend getting dressed up in corporate gear, stopping at the coffee shop on your way to the office, etc. There has been a lot of research that shows that this time will actually be applied to work endeavors, rather than leisure. That means you have the opportunity to be more productive, which makes a workcation a win-win for both you and your employer.
  • You can be more flexible with travel arrangements. As long as you are online and have the necessary tools (and your boss’ blessing), you can plan your travel as you see fit. Many people taking traditional vacations are bound by PTO or important deadlines. On a workcation you may be able to stay longer in your desired location. You can plan your trip around other things, such as weather, or activities you plan to do there. Having too good of a time to leave? As long as you are getting your work done, you may not need to.
  • You don’t waste vacation days. In America, we are notoriously bad about taking our own vacation time. In fact, we waste more than $2 billion annually by failing to use granted vacation time. PTO is a precious commodity and many people don’t even take full advantage of this part of their compensation because they are too busy, need team coverage, etc. By being able to work at least some of the time on a trip, you can get your work done and save those days. Many companies have PTO policies that combine sick time and vacation time, so more PTO days in your bank mean that you have a backup plan if something goes wrong (like a medical emergency). Plus, some companies pay for unused PTO time on an employee’s departure, so there might be a financial incentive for saving vacation time. There are plenty of reasons why you might not want to use PTO time, and a workcation means you don’t have to.
  • You can keep on schedule. As mentioned above, too many people don’t take vacation time because they simply can’t step out of their work schedule for a variety of reasons. Whether you don’t have coverage on your team or you’re working toward important deadlines, a workcation allows you to keep things moving and keep working toward your goals. In many situations, as long as your workcation is in the same time zone as your company, you can keep your usual schedule. This means you can be available, participate in meetings, and communicate as you normally would so that your important projects won’t miss a beat.
  • You can enrich your life in other ways. Being a well-rounded person is a great quality. Depending on where you’re going on your workcation (and what you’re doing), you may be able to meet new people, take in a new culture, or practice a new skill. You’re certain to find opportunities for personal growth that you wouldn’t find in your normal office. That’s a benefit to you as well as your employer.

Related Article: Top “Workcation” Destinations: Where to Work Remotely Around the World


The “Do's” of a Successful Workcation

A successful workcation doesn’t happen by accident. To have an effective working vacation - one where you do a great job at work, and enjoy your desired location and travel companions - requires a lot of planning. Here are a few things to make sure you DO:

DO: Get permission ahead of time

Depending on how flexible your work arrangement is, “permission” can vary from just mentioning it to your boss to creating a proposal and getting specific approvals. Regardless, make sure you follow your company’s policy and get the approval in written form, if possible. If your operation doesn’t have a policy, talk to your manager about your hopes. If this is something that is new to your company, we suggest starting with a (concise) proposal that lists:

  • What you’re hoping to do
  • Length of trip
  • Communication schedule, important milestones that you’ll hit, etc.
  • How this arrangement will impact your work (if at all)
  • Backup plans
  • How this workcation can benefit the company as well as you

DO: Select a location that will enable your work

You may already have a workcation destination in mind. For example, if you want to take an extended holiday season with your family in your hometown. However, if you’re planning a trip, it’s essential to choose a location that makes sense for getting your work done. For example, if you’re going to travel with a group of friends who will also need to work, it’s probably not a good idea to choose a one-room studio for your stay. For most people, connectivity is the most important factor. Is there wifi, and is it reliable? You’ll also want to consider who you’ll travel with and how you’ll use the space so that everyone has what they need. If traveling with children, where will they spend time when you work? When it comes to a workcation, your work needs to be at the forefront of your planning. Even the most beautiful mountain cabin is a bad idea if the wifi signal is spotty.

DO: Bring the technology that you need - and have a backup plan

Depending on your role, there’s a variety of things you might need to invest in prior to your trip. Most people need a cell phone and laptop to complete their work remotely. What else do you require? If you print documents, scan them, or file them, you’ll need to consider those elements. In addition to the tools, make sure you have chargers for all the hardware. We suggest bringing a second laptop and phone charger. You may also want to research what you will do if something goes wrong with the tools you brought. For example, if your printer goes down, is there a library nearby where you can print items? If you drop your phone in the lake, what will you do?

DO: Ensure you’re taking security precautions

This is a more important step for some people than others, but you need to check in with your company on their cyber-security measures and be sure you’re following protocol. This is particularly important for jobs in healthcare, finance, etc. That being said, there are many industries that handle sensitive information indirectly. For example, if you are a consultant, you may have billing records with sensitive financial information on them. Before leaving for your trip, be sure to talk to your IT team about how to handle private information from your location. Enable password protection on all of your devices, set up two-factor authentication, and always use the hotel room safe if one is available. Be aware that the WiFi connection you are using may be public, and closely monitor what information you are sending out.

DO: Set a communication cadence - and stick to it

If you will be working different hours than the rest of your team (and this has been okayed by your boss), then you want to document your schedule and make sure your team and any other stakeholders understand it. This means that all of your direct reports, key client contacts, and others you regularly interact with should know when you’ll be available. Beyond just making people aware, we suggest having a set window each day where you will be accessible. For example, if you will be on the east coast but your office is on the west coast, then maybe you commit to being online from 1pm - 5pm ET (or 10am - 1pm PT) every day. Additionally, it’s a good idea to schedule regular touchpoints, such as status updates on Friday mornings. The most important thing is to be consistent and to be available when you said you would be.

DO: Document results

Not that anyone would think you’re slacking off, but it’s a smart idea to keep track of what you are getting done on your workcation. How detailed you need to be depends on your own corporate culture, but at a minimum you should keep track of any important milestones that are being met while you are working. If you are a project manager, keep detailed notes on the different phases of your project and make sure there is an ongoing status report available. If you are in sales, document the number of phone calls, meetings, and contracts you're handling each day. The metrics that matter to your higher-ups will differ by role and industry, but simply keeping a short daily log will prove your productivity.

DO: Have a reliable contact at home

Pulling off a trip like this can be difficult without the right support in place. You don’t want to overly rely on people from your team, but you should have someone who really understands what’s going on and can be a point of contact for others. This person is particularly important if you will need someone to handle physical responsibilities like approving prototypes, dropping something off for an executive, collecting paper reports, etc.  In advance of your trip, do everything you can to make things easy for them. Make sure they are set up for success as much as possible, and stick to the communication schedule you set with them. The idea isn’t for them to pick up your work, but to be a point person if, for some reason, you become unavailable. Pro tip: make sure to bring them back a great gift with a heartfelt note of gratitude.

Related Article: The Ultimate Guide to a Successful Workcation


The “Don’ts” that Make a Difference

The best laid plans don’t always work out. A workcation isn’t guaranteed to be all sunshine and great wifi. Here are some things that people should know before they plan a working vacation. A lot of people have learned lessons the hard way. Some things that you DON’T want to do are:

DO NOT: Assume the answer is “no”

Workcation may be a totally new concept for your organization, but all forms of non-traditional work arrangements are becoming more common. As mentioned, remote work has become highly sought after and can be an important piece of employee retention. The working landscape has changed in many ways, for many people, following the pandemic. It never hurts to just begin a dialogue. Before preparing a robust proposal, have a quick conversation with your manager or a mentor at work. Get a feel for if something like this is even possible, and you might be surprised at the answer. There’s a first time for everything!

DO NOT: Travel in a large group

Though it can be exciting to plan a trip with your whole crew, it’s not ideal for managing your work life. Some people have tried a workcation as a way to tag along on what is a real vacation for others. That’s a good way to feel left out of the fun, and you’re also likely to slack off a little bit to join in other activities. Plus, there’s the noise you have to think about. You don’t want to be on key client calls with a rousing game of beach volleyball in the background. A workcation will work best if you travel with a single friend or two, your partner, or just your immediate family (who understand your work constraints).

DO NOT: Take the host’s word on the wifi

Asking if there is wifi available isn’t enough. You need to understand the signal, strength, and speed. Is it just enough to get a few emails out, or can it support a day of video calls? Too many people get burned by insufficient internet and end up investing in hot spots or new data plans in their location. Ask detailed questions about how owners use the wifi and be transparent about what you need to get your own work done.

DO NOT: Ignore time zones

Taking a workcation in the same time zone as your company and team will naturally make for a better trip. The fact is that being able to communicate with people on your normal cadence is going to streamline your day and your work. Plus, the truth is that asking people to change their schedule to accommodate your new time zone will lead to resentment. Additionally, many people think that they’ll adjust their own schedule to accommodate their organization’s time zone, but be realistic about this. If you are up into the middle of the night to speak to your colleagues, how sharp are you really going to be?

DO NOT: Forgetting to ask about length-of-stay discounts

So many short term rentals provide lower pricing for people booking a week or a month at a time. When you perform a search on Airbnb, don’t be scared off if the nightly price feels too high. Many hosts set up a weekly or monthly discount that is automatically applied when you select enough days in the booking functionality, but some don’t. Many of them still offer these discounts but you’ll need to ask and have a conversation. It never hurts to ask hosts if they will provide a discount for renting for longer periods.

DO NOT: Work non-stop

Once you plan your workcation and see all the PTO you’re saving, it can be tempting to want to work the entire time. However, it’s really important to schedule some down-time and really embrace the location of your trip (and the people you’re there with). At a minimum, we’d suggest bookending your trip with weekends, so you have 4 days of fun without work commitments. If you’ve taken the time and spent the money to travel to a destination, you might as well enjoy it!

DO NOT: Not setting expectations with travel partners

We referenced this above with the group travel comment, but you need to make sure that whoever you travel with understands that you’re actually working. Have a conversation about the key things you would both like to accomplish while on the trip. For example, what are the “must-see” sights you want to hit? Is there a restaurant your spouse really wants to try, or a hike your friend has heard about? How much time will you have to sit on the beach vs. sit on your laptop? Setting expectations early with your travel companions will mean everyone has a better time.

DO NOT: Ignoring potential challenges

Obviously, workcations come with a big upside for the employee. However, it’s crucial to be realistic about the hurdles the arrangement could pose for your employer or your company. Could there be a negative impact in any way, such as putting more pressure on team members? If so, give real thought to these obstacles and then solutions. You’re likely to be asked about how you can manage these challenges, so you might as well have solutions planned.

How Productivity Tools Can Help Your Workcation

There are a lot of tools out there that can support a workcation or other remote arrangement. Everything from mobile hotspots to team chatting apps to video conferencing suites will make your workday more productive and collaborative. As you prepare for a workcation, we suggest you make sure you have the following platforms available:

  • Mobile hotspot
  • Team collaboration app
  • Screen sharing software
  • Screen recording tool
  • Video conferencing tool
  • Cloud storage
  • To-do list app (like Todoist)
  • Project management app (like Asana)
  • Security or password tools
  • Productivity app (like Shift)

Related Article: Top Productivity Tools & Apps for 2022


No matter where you end up on your workcation, Shift can help you to streamline and manage your work. Shift is the desktop app for streamlining and collaborating across accounts and workflows, and allows you to skip the logging in and out process. Users love Shift because it helps them to collaborate and complete work from anywhere. Review a full list of features here.