5 Things to Consider Before Taking a Workation

If you haven’t yet heard of the buzzy portmanteau, workation, it’s exactly how it sounds: work + vacation. Workations allow you to work remotely from a destination other than your typical home-base, giving you the benefit of exploring new places in your evenings and on the weekends, without having to compromise precious vacation time. It’s a trend that has been around for a while, but has recently resurfaced in popularity during the era of COVID. We recently hosted a Clubhouse chat with a few App in the Air community members who are well-versed in the workation life themselves: Ashley Castellanos, Haley Hosea, and Wesam Taleb. Here are their top tips:

1. Have a plan for secure Internet

This first tip is a given, but something each panelist touched on. You can’t embark on a workation without doing the “work” part, which for many, requires a stable Internet connection. Haley’s fool-proof strategy to ensure good Internet on a workation starts with securing accommodations that advertise WiFi. She books her stays through Airbnb, and filters for WiFi listings when looking at included amenities. Her backup weapon is a WiFi hotspot called Skyroam, which really ensures that she can work from anywhere.

2. Be transparent with your colleagues

Communicate with your colleagues about where you will be working remotely from. Wesam emphasized the importance of this in the event of an emergency—if your team is aware, they can act as a layer of support and help cover for you. Additionally, communicating with transparency will build your team’s trust in your ability to work from anywhere. Who knows? They may even be empathetic to time zone differences and accommodate your schedule.

3. Regularly check COVID guidelines

While travel is indeed on the rebound after a turbulent year, countries around the world are recovering at different rates, meaning COVID guidelines will continue to vary from place to place for the foreseeable future. You can use App in the Air’s COVID tool to check travel policies between specific countries and to review the latest airline rules.

4. Prepare yourself for the unexpected

Ashley shared that while she is a natural planner, she has learned through her travels to embrace the unexpected.

There have been many instances where things did not go according to plan, or things went wrong, and you just have to be very open-minded and just know that it’ll be okay and you’ll get through it. If you try living this kind of lifestyle—working remotely and traveling—it’s fun, but it does have its set of challenges and you need to be very open to the experience.

5. If you’re thinking of taking a workation — do it now

There truly is no time better than the present with most companies having implemented remote work policies during the pandemic. The panel discussed their respective work situations, with the general consensus being that their employers may be asking employees to begin their return on-site by the end of 2021. Wesam suggested taking a workation, even if the destination is somewhere not too far from home, emphasizing the point that merely changing your scenery can be a great adventure in itself.

More about the panelists…

Ashley Castellanos

Ashley is a marketer, photographer, and content creator who at the age of 24, made the bold decision to live abroad in six countries across Europe and Asia over the course of five years! Although now back in Portland, where she is based, Ashley is patiently awaiting the day she lives overseas again. She discovered App in the Air when planning a trip to Philadelphia in 2020, and loved it so much that she even compiled a video review!

Haley Hosea

Haley works in management consulting, in which the nature of her work has turned her into a frequent flier. Similar to Ashley, she also discovered App in the Air in 2020. A few months after the pandemic hit the United States, she was feeling the itch to leave home in Bryan, Texas, and decided to embark on an “extended” road trip! Haley is now in the tenth month of her adventure, exploring the eighth state in her journey. She is an advocate for slow travel, spending several weeks at a time in every destination.

Wesam Taleb

Wesam is an IT professional based in the Dallas Fort-Worth metro area who has been using the app since 2019. He primarily travels for fun, and is always looking for his next adventure. His goal has been to explore somewhere new at least once every month, with his latest adventures spanning across Utah, California, and Colorado.Wesam experienced the workation life, having spent some time working remotely from Mexico and the U.S. Virgin Islands.

You can join us for more conversations like this one by following the App in the Air Community on Clubhouse. Send us a message at [email protected] if you’re looking for an invitation to join the exclusive audio chat platform.

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