How and why to take a workcation

Traveling to a far-flung or interesting location and working remotely is becoming more common. Here’s why a workcation might be right for you and how to plan one.

One of the intriguing aspects of the shift to remote and hybrid working is that workers that previously located themselves in proximity to their office are no longer tethered to any specific space. Many of us took advantage of that fact during the pandemic. Perhaps you or the person on the other end of a video conference might have mountains in the background one week and palm trees the next.

SEE: Home video setup: What you need to look and sound professional (TechRepublic Premium)

These ad hoc trips have evolved into the formal idea of a “workcation,” or traveling to another location intending to work in that spot rather than focus primarily on rest and relaxation. While the concept is still new and might seem somewhat devious, when done well, it can benefit both the employee and their employer.

Simply changing one’s scenery can improve productivity and work-life balance, at least anecdotally. It’s also an easy way to offer a tangible benefit to employees with minimal cost to the employer.

The logistics of a workcation

If you’re considering a workcation, your first impulse might be to book a trip to your favorite vacation spot, perhaps with visions of virtual meetings in the morning and margaritas on the beach in the evening. However, the factors that make a great and relaxing vacation don’t always match an effective workcation.

For your initial forays into a workcation, consider a limited period. Two weeks is a good start, as that allows you enough time to experience your new location as well as the benefits and drawbacks of working away from your usual home base. While it can be tempting to jet off without telling anyone, it’s worth running the idea by your colleagues and leadership. Come with a plan and specific details of how the workcation will benefit the organization, or at least allow you to be just as effective as you are working from your home.

You might even pitch the workcation as highly beneficial to your company. If you work on a global team, perhaps your workcation location might coincide with a key international office or allow you to work in the same time zone as a team with whom you frequently collaborate. Proximity to a regional or international office can also help should you have connectivity or technical problems. A nearby office can also provide a group of individuals that know the local area and can help you get settled and experience your temporary home like a local.

Once you arrive at your workcation destination, it’s worth staying “overconnected,” at least for the first few days, especially if you’re a workcation pioneer at your company. Try to match your home working hours unless explicitly working local hours brings a particular benefit. Don’t be shy about sharing an occasional story about the benefits of being in a different location, whether it’s increased energy and focus or the establishment of new personal connections with colleagues in a different office.

Workcation challenges and tips

Perhaps the thorniest challenges to a workcation are legal and tax issues, particularly if you’re considering an international destination.

Even if you’re a U.S. citizen and stay within the U.S., most states tax income earned while present in that state and require an individual to file a tax return. In some states, as little as an hour working in that location requires you to file a state tax return there. Be prepared to track the hours you work in your alternate state and have some extra cost and administrative work during tax season to make the correct filings.

Internationally, some countries consider you an in-country worker and require a work visa after some period of time. These issues are highly complex and deserve some research before jetting off to another country for several months. Interestingly, an increasing number of countries are creating “digital nomad” visas that allow for long-duration stays and streamlined applications.

Aside from the legal and compliance legwork required for a workcation, make sure you think through the logistics of seemingly basic questions like:

• How will I get around in my workcation location? Will I need to budget for a rental car, train pass, bicycle or other mode of transportation?
• Is the internet quality acceptable, and are connections reliable?
• Can I communicate well enough to facilitate basic needs like food shopping, getting around town and dealing with basic service questions?
• Do I need any special phone plans, electrical adapters or equipment?
• What will I do with my residence? How will I pay my bills and check on my home?

Start small, perhaps visiting a friend or family member in an interesting location, and see if you can stay productive while away from home. Set yourself up for maximum success to test whether you enjoy the workcation concept and prove that you can remain effective and productive. After a few successful test runs, consider longer or more logistically challenging workcations.

Spending a longer duration in an exciting location is one of the great benefits of remote and hybrid working and has rewritten the rulebook for how and where we work. Whether you’re starting your career and infinitely flexible, or have a family and are a senior leader, you can likely design a workcation that works for you and your employer.