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The Ultimate Guide to a Successful Workcation


Simon Vreeswijk

Director of Marketing - 08 Aug, 2022


Everyone loves vacation. What’s not to love? Work is sometimes a different story, but things are changing.

If the past couple years have shown us anything, it’s that we are operating in a new work landscape. Now, people can get the benefits of vacation without stepping away from their work. A workcation is the best of both worlds. Here are some of our best tips for a successful workcation.

Related Article: A Guide to Making Working from Home Work for You


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.

A workcation allows workers to have flexibility in their location and more control over their workdays. Additionally, these arrangements allow employees to make the most of limited vacation time policies. There’s been plenty of research that shows Amercians’ work-life balance is far from optimal, leading to burnout and negative impacts on mental health. Being able to work from anywhere allows people to spend more time with family, enjoy their surroundings, and plan travel to new and interesting places. Additionally, research from Travel Pulse shows that:

  • 86% of employees either agreed or strongly agreed that a workcation boosted their productivity, and 81% said they became more creative at work after taking a workcation.
  • Nearly 69% of workers were less likely to quit their jobs after going on a workcation and 84% felt more satisfied with their job.
  • A combined 83% of participants either agreed or strongly agreed that a workcation helped them better cope with burnout.

How to Ask for a Workcation

For many people, a workcation is a normal state. For those that are self-employed or even used to remote arrangements, traveling while working might be usual. For those who are employed by others or work in a traditional office environment, you may need to get special permission. Even though the pandemic has presented lots of new opportunities for working elsewhere, it’s important to get an “okay” from those who oversee your work.

Many people assume their bosses won’t like the idea, but that attitude is changing. Start by acknowledging that you know it’s a big request, and maybe unprecedented in your workplace. Explain that trying this arrangement would be good for your morale and well-being, and that it would make you a more loyal and engaged employee.

Make your request simple and explain the circumstances. You can try something like “I know this might be a little bit out there, but I was hoping to work remotely for two weeks this summer. I think being out of the office would help me to clear my head and get refreshed. I have the opportunity to spend time with my extended family, and I’d like to have that experience, while also managing my projects and making sure my workload doesn’t stagnate.” You can talk about the ways in which you plan to keep up with work and don’t want to keep the company hanging.

If you think you need to take a more formal approach, write out a proposal that details the following:

  • The schedule you’ll work (and when you won’t)
  • Any time that you will be officially “off”
  • How you can be reached while away and what tools you have available
  • Which meetings you’ll attend (or won’t)
  • The tools that you have available to help you connect and collaborate
  • How you’ll pass off any work that you may not be able to complete

Before Planning a Workcation

Sounds simple enough, right? If you’re convinced that a workcation is something you can do successfully, you need to do some planning and preparation. Here’s what you need to think about as you plan to work from another location.

  1. Know your company policies. Is a workcation even something you can do? Even after most people’s work environments have been radically altered, there are some employers who are not going to be excited about remote workers. And there is some work that just simply can’t be done remotely. What is your HR policy? Are there certain hours that you need to be available? What technology do you need, and do you have it?
  2. Assess your goals. Why do you want to take a workcation? Will you focus more on work, or on vacation? Are you hoping to just do your normal job from a different location, or do you want to cut back on work hours and enjoy some more down time? You need these answers so that you can consider where to go (if your location isn’t set in stone) and what accommodations you need. If you know you want to work your regular hours, then you may need to look for wifi, a designated working space, etc.
  3. Where are you traveling? You may have a destination in mind (for example a ski trip with friends), or you may be open to something new. Over the past two years, many people researched new areas with the idea of moving short-term and working from there. Do you want to go to a beach, or the mountains? Think about how far you want to travel and what logistics look like. Right now, flying comes with some degree of uncertainty, but that’s likely to change. As mentioned, figure out what you need for work, but also think about the comforts of home you want. What transportation is available, and what are the rental options? What’s your budget? What’s important to you?
  4. How long will you stay? One of the toughest things to consider is the length of your workcation. If you have a normal home base with pets, kids, or other responsibilities, then an extended workcation might be tough. In order to have enough time to develop a routine and be truly productive, your trip should be at least one or two weeks. Much shorter and you will spend more time getting settled than actually working.
  5. Consider rental options. Are you looking for a hotel room or a longer term rental? If you plan to split your time between working and leisure, a regular hotel room might be just fine. If you’re hoping to blend in more vacation activities, consider a rental like a condo or cabin. Mountain cabin rentals became very popular during the pandemic, for example.
  6. Figure out the space you need. Along with understanding the type of rental you need, think about other specifications. Do you want to make your own meals? Then you’ll need a kitchen or at least a kitchenette. Are you traveling with friends or family? If so, where will you get privacy for phone calls? Is there space to set up your necessary working arrangements? Will a dining table suffice, or do you need a dedicated room? What about parking? Of course, connectivity is a big deal. Even if everything about the space is great, if your wifi is poor, your workcation will not be successful.
  7. Consider who you’ll be traveling with. Are you going somewhere alone, or with your friends or family? What are their schedules, and the requirements of their work or school day? If there is one dedicated working space, who will be using it, and when? Who will be watching children if you and your spouse are both working during the day? How will you get privacy for important phone calls? Think about what the day-to-day of your workcation will really look like, and how you will operate in that environment.

Related Article: Notification Muting + Vacation Responder: How to Master “I’m Busy”


Tips for a Successful Workcation

If you’ve followed the above steps, you’ve probably planned a workcation that you’re excited about. Here’s how to make sure you’re productive and effective, work-wise.

  1. Get explicit permission. Don’t make the mistake of trying to take a workcation without clearing it first. Even if you normally work remotely, it’s a good idea to give your boss a heads up. Make sure that your clients, management, and team members know your plans, and outright ask for approval if necessary. The important thing is to be transparent so you know you’re not going against company policy.
  2. Build a communication cadence with stakeholders. Once you have approval for your workcation, let people know how often they’ll hear from you. Reassure people that you’ll be available, and let them know the schedule you’ll keep. It’s a good idea to set up regular weekly or monthly check-ins, and then stick to that commitment.
  3. Use the right tools. Do you need another phone line? What hardware do you need to take (such as a printer)? You also need to balance personal and professional tools. When you’re on workcation, you’ll likely be managing technology for your work life and your personal life. Chances are you’ll have multiple instances of different platforms on your laptop. This is where Shift comes in. Use Shift to streamline and collaborate across accounts and workflows. Shift can also help you talk to your colleagues and work teams using software like Slack.
  4. Stick to your routine. Having a structure to your work days is really important. You need to have clear lines between work time and vacation time. Many people like to use the “90 minute rule”, which organizes your work into 90 minute sprints that are optimal for productivity. Plan to take breaks in between to give your brain a rest.
  5. Check and double check wifi connections. If your work requires being online, then you won’t get very far without a good wifi signal. Have you tested the internet connection? What is your backup plan? Many people choose to invest in a hotspot device that they can take with them.
  6. Have a backup plan. Speaking of wifi, what are you going to do if the wifi goes out where you are staying? What if something goes wrong at the location where you’re staying (for example, a power outage in a mountain cabin)? What will you do if there is a key client deadline that is outside of normal working hours, or you need to put out a crucial fire with your team? How quickly could you get back to the office? It’s important to think through multiple scenarios of how things could go awry, and what you’ll do in those instances. You may also want to cover this information with your boss if they are uneasy about your plans.
  7. Set expectations with travel companions. When you set up your workcation arrangement, you likely agreed on a schedule that you’d be available. It’s important to make sure you really are accessible. If that means limiting leisure activities, that’s what you should do. Additionally, talk to the people you’re traveling with and let them know when to leave you alone. This is particularly true of children. If you have a dedicated work space set up, make sure people know which hours you’ll be using it.
  8. Set boundaries with colleagues. Just like you need to set expectations with travel companions, you’ll need to set them with co-workers. Let them know when you plan to be “off-duty”. If you have special activities planned or hope to spend evenings with your family, make sure your clients or colleagues understand this. Sticking to a regular work schedule and routine will really help with this.
  9. Exceed your work goals. You know what constitutes a “good job” in your role. Set goals for your time on workcation, and then do your best to exceed them just like you would in any scenario. The more great results you can show at the end of your trip, the more likely you’ll be able to take another workcation. Similarly, proving you can exceed milestones even when away will make it more likely that others on your team can try a workcation (which they’ll appreciate)! Write down short-term goals and the metrics associated and how you’ll measure them, then do your best to meet those goals.
  10. Enjoy your workcation! Remember that there’s a reason you planned a workcation in the first place. Take the time to enjoy your surroundings, get some down-time, explore, and spend time with people you care about. A workcation is all about working hard and playing hard. Take advantage of this unique opportunity! If your workcation works for everyone, then you may be able to make it a tradition.

Shift is the best way to collaborate and get work done, no matter where you are. Connect all of your email accounts and your favorite web apps and tools to Shift. Then, customize your workstation so it's just right for you. Download Shift now and set up your work just the way you want it - where you want it.