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5 Tips for Getting Paid While You Work from Anywhere with Bleisure Travel

Kylie Stine | Mar 2, 2022

Sometimes we’re in desperate need of a change of scenery, but our work schedule just doesn’t seem to allow it.

We’ve all been there. We sit surrounded by mountains of papers, eyeing yet another calendar reminder that pops up on our computer screen. We scroll through our social media feed (don’t deny it!), see our friends and influencers on exotic vacations, and enviously wonder, “Do they even work?”

We promise ourselves a quick getaway, but then we get distracted by daily to-dos like laundry, grocery shopping, and cleaning. It’s easy to get caught in a seemingly never-ending cycle, believing things would fall apart if you actually took a break and traveled.

Here’s some great news: you can continue to be the person who does it all — and you can do it from anywhere in the world!

Whether you call it bleisure travel or being a digital nomad, this style of travel is becoming increasingly popular. Some believe it may be redefining work-life balance. Just because two weeks off work may be out of the question, that doesn’t mean you have to be in office the whole time. And since the coronavirus pandemic, it’s not only more desirable, but also easier, to work from anywhere.

What is bleisure travel? 

The most popular form of bleisure travel is when an employee is traveling for business and extends the trip a few extra days, thus turning the business trip into a leisure vacation of sorts. On trips like these, travelers can often return on flights paid for by their companies or receive a business rate on airline tickets.

Another increasingly popular form of work is the ability to work remotely, which lends itself well to the bleisure and digital nomad movements. Even if your career field doesn’t offer full-time remote jobs, it may be possible for you to spend a week or two on a “business vacation” where you can work on the road.

With your dedication and these tips, you can get some R&R without missing any deadlines (or sacrificing a paycheck).

1. Remember that work still comes first.

Woman with travel insurance types

When you’re still being paid like it’s a regular workday (or if you’re being paid to travel for work), that means business is still your first priority. You’re most looking forward to evenings and weekends, but stay dedicated during the days so that you can enjoy your free time. Work hard, play hard!

If you’re meeting with clients or colleagues in your new location, use this opportunity to ask them about local hotspots. You’ll get the inside scoop, and you just might find you look forward to going to work more if you know you can ask for more great tips the next day.

2. Break up your days.

Woman with travel insurance schedules day

It can sometimes be difficult to stare at a screen for eight hours when daily to-dos and other distractions are competing for your attention. To combat this, set mini goals for yourself throughout the day, and then take short breaks to reward yourself.

For example, if you have 10 items on your to-do list, check off two items before making another cup of coffee or treating yourself to a pastry from that cute shop you discovered on the corner. Check off five before you go to lunch and try a local specialty. Switch locations after you check off seven. The workday will be more enjoyable, and you’ll still feel like you’re on vacation as you change up your workspace.

3. Keep your Wi-Fi connection in mind.

Woman with travel insurance listens to music as she types

If you know you have a call coming up, have to send an important email, or need to edit a Google doc, make sure you’re always somewhere with a sufficient internet connection. Some companies will provide you with a mobile internet hotspot when you’re working abroad, so ask your boss about helpful technology before you leave.

If an internet hotspot isn’t in the cards, going off the grid might not be the best plan for a bleisure vacation. Save the secluded cabin in the wilderness for another time.

4. Find settings that make work fun.

Woman with travel insurance types in the mountains

Ditch the hotel room and spend your days working in cafes, parks, coffee shops, or even another fancy hotel lobby instead. Look online for recommendations or ask the locals.

If you plan to be a digital nomad for an extended time, maybe even a few months, consider the services of a company like WorkMango. As one of Seven Corners’ partners, WorkMango helps you work remotely from the Caribbean by arranging accommodations and other logistics for you. All you have to do is join the community and show up with your laptop.

5. Remember that when it’s done, it’s done.

Woman with travel insurance relaxes by canal

Your boss (hopefully) approved your vacation, so don’t punish yourself for physically being out of the office. There's no need to spend your entire trip working. If you met your goals for the day, close your laptop and enjoy your evening. You are on vacation, after all!

Now all you have to do is decide where to work remotely and what kind of travel insurance you need to do it safely. Seven Corners can help you choose which travel insurance plan is right for your next working holiday. Contact us with your questions or get a quote online.

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