How To Plan a Successful and Fun Workcation

While smushing the two words “work” and “vacation” into the same sentence seems like it should be illegal, the fact of the matter is that sometimes we can’t always 100% unplug from our work. And although there are times when we wholly need to (and deserve to!) have a completely unplugged vacation away from the musical symphony of dings and buzzes from Teams and Outlook, there are also times when planning a workcation (or working vacation) is just the thing we need to balance both productivity and relaxation.

What Is a Workcation?

A working vacation, conveniently referred to as a workcation, may sound like an oxymoron, but it is becoming more common among working individuals, especially during the Covid-19 pandemic. The pandemic caused a vast majority of organizations to press pause and find ways to pivot jobs from onsite to remote. With the convenience of working at home, people discovered that they could travel out of state to take care of loved ones or explore new sceneries without missing a (work-related) beat. Whether they were keenly aware of it or not, these traveling and working individuals were discovering the fine balance of a working vacation.

Why Take a Working Vacation?

While a workcation may sound like you’re not really working and not really on vacation, when done successfully, a workcation can be a perfect balance of both. But why take a working vacation? Here are just a few reasons.

You are a Freelancer or Entrepreneur

While being a freelancer and running your own business means you can set your own schedule and be your own boss, it also means that you probably have a string of regular clients and a number of projects and deadlines you need to juggle. In cases like these, a workcation could be just the thing you need to stay on top of your work while refreshing your soul with some new places, faces, and spaces.

You Want to Preserve Vacation Time

Maybe you’re not a freelancer or entrepreneur, but you are able to work remotely for your full-time job. Planning a workcation is a great way to preserve your vacation time. In instances where you may have a short two or three-day trip, you can utilize the convenience of a workcation. By doing this, you can still do your job during set hours and have time to explore during your off-hours. The best part? You can save your paid time off for a much longer vacation down the road.

You Need a Change of Scenery

Sometimes, life can feel a little stagnant. Whether you’ve been cooped up in the house too long and can’t stare at the crack in your ivory wall for another second, or if you’re feeling a bit melancholy and need a change of scenery, a working vacation is the just the thing to shake up your routine and add some pizzazz back into your step.

You Want to Create Fresh Content

Taking a workcation is also a great way to create vibrant, new content. YouTubers, social media influencers, travel writers, and food bloggers can not only enjoy but thoroughly benefit from taking a working vacation. Traveling to a new destination provides ample opportunities to create fresh content featuring timeless sights, delicious foods, colorful fashion, new cultures and customs, and so much more.

How To Plan a Successful Working Vacation

Balancing work and relaxation during a working vacation is absolutely doable when it is intentionally planned. Here are just a few key tips for preparing for and planning a successful working vacation.

Notify Your Clients and/or Job

Whether you’re a freelancer or a full-time corporate employee, the best thing to do when planning for a workcation is to let all clients and managers/bosses know ahead of time. The more notice you give your clients and manager, the more time you all have to work out a comfortable schedule and take care of any supremely urgent priorities before you go.

Provide a Backup Plan

Although you will still be working on a workcation, it never hurts to have a backup plan. For freelancers especially, letting your clients know that you already have thought of a backup plan—should they need it—is both reassuring and, quite simply, the professional thing to do. Backup plans can be as uncomplicated as offering a client a secondary way to contact you or can be more ‘literal’ by providing a backup writer/designer/photographer should your client have a pressing matter that arises while you are away.

Pro-tip for freelancers: Not sure where to find a backup freelancer to fill in if you’re unable to tackle a last-minute task? Explore the talent on Fiverr in your industry. Read through profiles, search through portfolios, and if you find someone that you think fits your style and caliber, reach out and build a connection. Chat with a few freelancers to see if any of them would be comfortable filling in for certain projects and tasks while you’re out of state on a workcation or outsourcing during busy seasons when you have an overflow of projects.

Research and Coordinate Time Zones

To plan a successful working vacation, take the time to research and coordinate time zones. This step is an absolute must. You may be traveling to a location that is the complete opposite from your current time zones. Whether you’re an hour ahead or 35 hours ahead, knowing the time difference and setting realistic expectations with your clients, manager, or coworkers is crucial. Make sure to email your time zone information and when they can expect responses in an email to all your corresponding parties. Doing this is not only helpful but provides written documentation proving you have clearly outlined and notified all parties of your expectations and boundaries, should you need to reference it in the future.

Ensure You Have Access to Wifi

While lounging in a magical treehouse suspended in the deep woods with no access to technology is great for a fully unplugged vacation, for a working vacation, having solid access to the internet is a non-negotiable must-have. If you’re staying in a hotel, check to see if there is free wifi available or if you have to pay to have access. If you’re renting a room via Airbnb or some other rental site, make sure to read through the description to see if wifi is a feature provided during your stay.

Designate Time to Hunker Down and Work

The key to balancing fun and relaxation on a working vacation? Designate time to work and time to relax. Instead of trying to squeeze in time to work in between little bouts of free time, create a specific schedule where you carve out time to hunker down and get things done. It may also help to let your managers, coworkers, and clients know your designated work hours in case they need to directly connect with you. Use this time to get deeper, more complex work done and schedule any team or client meetings. Allocating time to work may not sound fun. Still, it will allow you to focus during workcation hours and gives you the freedom to unapologetically unwind, explore, and enjoy everything your new work location has to offer during your off time.

Hop into (Working) Vacay Mode

At the end of the day, life is too short to be bogged down in work 24/7 and it’s too short to wait for a pile of vacation days to accrue. A working vacation is a perfect way to take care of your responsibilities but still enjoy the present moment in a new destination. By providing thorough schedules and emergency backup plans with your clients and managers ahead of time and by carving out purposeful time for work and time for play, you can plan a successful (and fun!) workcation. For more fun tips and tricks for freelancers, be sure to check out the Fiverr blog for helpful resources, trending topics, and more.

How To Plan a Successful and Fun Workcation

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