← Return to Blog

How to Get Paid While You Work from Anywhere

Becky Hart | Sep 20, 2022

Share Twitter   share

Woman working remotely from a cafe.

When you can work from anywhere, you can also live anywhere. It changes everything from your commute to flexibility for caring for family. And it opens the door to more bleisure opportunities than ever before.

Remote work has been steadily on the rise, both in the form of bleisure travel and digital nomadism, for quite a few years now. But with the advancements in technology and the unexpected “Great Remote Work Experiment” necessitated by the pandemic, the world of work has shifted on its axis. Many experts predict that a full return to the office isn’t in the cards.

It's a shift that Marc Cenedella, CEO of Ladders, a career site for professionals seeking six-figure jobs and ongoing vocational enrichment, described to NBC News as “The largest change in American working and living arrangements since World War II.”

The ability to work remotely may be redefining work-life balance. When we crave a change of scenery but can’t take two weeks off work, bleisure travel can be the answer. When your employer no longer requires you to put in face time at a brick-and-mortar office, the digital nomad lifestyle could be the solution.

Pulling these off while still being a model employee is a little more complex than negotiating a treadmill desk or flex schedule. Try these top tips for getting paid while you work from anywhere.

Digital nomads working from a cafe.

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.

Being a digital nomad is a bit different. For starters, a digital nomad tends to stay away from home longer, perhaps working remotely for several weeks or even permanently. They also aren’t usually tied to their clients’ location or the site of a conference they’re attending.

Both bleisure travelers and digital nomads enjoy a great amount of flexibility in where they work, however, and can benefit from all the opportunities that come with exploring the world while technically on the clock.

Man working off iPad with a view of the city.

Know Before You Go: How to Prepare to Be a Digital Nomad

To succeed in your remote work endeavors, you need to do some homework before you hit the road. Your boss — even if you’re your own boss — wants to know that you’ll still be productive and can avoid distractions and get the job done. Plus, you’ll need to set yourself up for personal success. This could be the adventure of a lifetime. You don't want to let a lack of planning derail the opportunity.

1. Explore the financial implications.

Understanding your finances in advance will help you take advantage of them. Meet with an accountant or financial planner who understands remote working so they can advise you on taxes, expenses, and how to fully maximize the experience.

“If you will be staying for an extended period of time in one country, contact a tax expert in that country to understand any tax implications while working there,” says Dan Bagby of HoneymoonAlways. “Portugal, for example, considers anyone with a residency a tax resident, which can drastically change your financial situation.”

Dan should know a thing or two about being a digital nomad. Together with his wife, Michelle, he moved from Texas in 2021 to run their travel business full-time from Portugal.

Just as you would if you were working in one location, build a savings fund for unexpected expenses. As a long-term digital nomad, you might not need home maintenance at this time, but you could need a new pair of headphones for virtual meetings or to replace a cracked laptop screen.

Think about how you will pay for expenses, too. You might want to use a travel credit card as your primary source for paying for everything. Also, have access to local currency and a backup payment method. Credit cards usually offer the best exchange rate, but in the event of a system being down or lack of service in a remote area, you will be covered. Let your banking institution and credit card companies at home know you’ll be traveling so they don’t deactivate your accounts for what they think is suspicious activity in another location.

Decide if you want — or need — to be debt-free before you go. Some digital nomads choose this lifestyle because it lets them pay down their debt. Being debt-free means you have one less expense to worry about. You'll have more flexibility in your budget and lifestyle. If you have a slow month or find yourself in a place that you really want to explore, you can do so without worrying about making enough money to cover your rent and a credit card payment.

2. Bring a friend.

If you’re doing short-term bleisure travel, many employers will let you bring a friend or family with you. Research from Expedia shows that 65% of bleisure travelers go on their own, with 35% bringing someone with them.

Visiting friends and family at or near your destination is great, but only 36% of bleisure travelers have people they know near their destination. There’s something to be said for solo travel, but having a travel buddy can make your bleisure trip even sweeter.

Long-term digital nomads can also benefit from bringing friends or family. They can serve as a built-in support system if you’re experiencing culture shock. If, when you examined your finances, you find that solo travel might be hard on your budget, having a travel companion to share expenses with can also make it possible to stay on the road longer.

Remember, too, that your travel companion doesn’t have to be with you 24/7/365. While some couples start a business together abroad, others keep it more casual. Some studies estimate that while 61 percent of digital nomads are married, only 31 percent of those travel with their partner full-time.

3. Get your travel documents in order.

If your remote work is taking you overseas, you’ll need to apply for a passport and pay the appropriate fees. This can take eight weeks or more, so plan ahead.

Find out if the country where you plan to stay requires a visa, and determine if you can get a visa upon arrival or if you'll need to apply for one in advance. You may need to appear in person at the country's embassy in your home country to get your visa, or you may be able to apply by mail. Each country has its own process, so consult its official government website or embassy in your home country. 

4. Line up work before you go.

Assuming you aren’t just tagging a vacation onto your business trip, you’ll want to arrange work before your adventure begins. Few things will be as disappointing as having to cut your trip short because you couldn’t earn a paycheck.

The months leading up to your new life as a digital nomad are great for thinking about the type of work you do and don’t want to do. This doesn't mean you have to find a new job. If you're already working remotely or have a job that doesn't require being in the office, your current employer may have no problem with you taking your work overseas.

Some digital nomads start their own businesses. If you choose this route, line up work before you go so you'll be less likely to take a job you don’t like just so you can pay the rent.

5. Choose a location. 

For many digital nomads, figuring out the best places to work remotely and choosing where to go is the best part of the lifestyle. The key is finding a place where you can balance your work and life demands. You need a place where you have access to reliable internet and that appeals to your interests.

One important consideration is the type of climate you prefer. Do you like hot, humid days with rainy afternoons? Would you rather be in a place where you need a jacket in the early morning or evening? You want to be as comfortable as possible, so look for places with the type of weather you like best.

Consider the environment and opportunities for recreation and learning that you'll enjoy. For instance, do you want to live near the ocean so you can scuba dive, surf, and sunbathe? You might prefer a large metropolitan area with activity at all hours of the day and night, or you might want to have a quieter retreat in the countryside while you work. If you enjoy history, consider a location that has plenty of museums, ancient architecture, or opportunities for archaeological digs.

No matter where you end up and regardless of how long you plan to stay in a single location, look for a support community. From spending hours online in shared workplaces or making friends at cafes that know your order by heart, it is important to have connections throughout your travels. Researching digital nomad groups and shared message boards might help you find recommendations and pick up some tips from those who have experience in this working style.

Where you choose to work as a digital nomad will have a large impact on your happiness and quality of life. Check out the best places to work remotely around the world.

6. Be open to opportunity. 

Short-term bleisure travelers have less riding on their choice of location. It’s probably already chosen for you in the sense that you go where your conference is, the site of your client meetings, or wherever your company’s satellite office is located.

The decision to plan a bleisure trip in the first place, instead of a business-only trip, depends on the destination. Of course, look for activities and attractions close to your temporary home base, but remember that there’s also nothing keeping you in the same spot where you're doing business.

A survey conducted by Great Hotels of the World shows that 28% of bleisure travelers don't stay in the same location for business and leisure. There’s no rule that you can’t rent a car and drive to an amazing second destination or discover the beauty in an area you may not have considered for vacation otherwise.

7. Familiarize yourself with the culture.

This tip is especially important if you’re transitioning into a digital nomad overseas, but it can be equally helpful to those visiting another country for a short-term bleisure trip.

Living in another country can be a culture shock, and it may take some time and experience to learn how to navigate everything from how to stand in line at the coffee shop to when and how to renew your visa. It can also help to brush up on business etiquette. Do you shake hands, bow, or kiss cheeks (and how many times?!) when meeting a colleague? Is it considered rude and confrontational to voice different ideas in a large meeting, or are dissenting opinions valued?

If you're going someplace where you don't already know the language, consider lessons to at least pick up some basic phrases or try these 10 tips to help you learn a new language.

8. Take care of obligations at home.

When you make an inventory of all your local obligations, you might be surprised to see how many you have. Check your calendar for events you agreed to attend and determine if you need to cancel or make arrangements to return for the engagement. If you’ll be gone long term, cancel or put on hold your gym membership, subscriptions, and internet service. If you're leaving an apartment, decide whether to break the lease or sublet the space. If you're quitting your job, you need to give them enough notice.

Man working remotely from hotel cafe.

Time to Work: How to Be a digital nomad

Now that you’re fully prepared for your remote work adventure, stick to this advice to get the most out of your time on the road.

1. Remember that work still comes first.

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.

Practice smart scheduling. If you’re a bleisure traveler on a shorter stay, try to use the calendar to your advantage. Schedule your business trip near a long weekend or public holiday so you can extend your trip without using as much paid vacation time. You might be able to book leisure activities during either end of your trip. If you have evenings free, be sure to use them to try out a fabulous dining hot spot or catch a show.

You might also consider the level of activity you'll be engaging in. For example, if you're planning an epic hike or shredding the slopes, you might schedule your leisure time after business so you're not too physically exhausted. After all, to make bleisure travel a success, work has to come first.

2. Find settings that make work fun.

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, which 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.

3. Break up your days.

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.

4. Plan time off.

Settling into being a digital nomad means recognizing that this isn’t a vacation, but rather a new way to work and live. Shift your mindset away from thinking you have to see everything in a week as you would on an ordinary vacation.

Take time to settle into your new location and remember that you’ll have plenty of opportunity to explore in the coming weeks or months.

  • When you arrive at your destination, try to plan a day or two to get organized with your work and to transition to your new time zone.
  • Scope out coworking spaces or set up your work area if you prefer to work at your accommodations.
  • Test your internet connection and review your calendar for work meetings for the next several days.
  • Make sure you adjust for any time differences to avoid mix-ups with deadlines or meeting times.
  • Once you are set up and ready to dive into work, take some time to complete essential tasks like food shopping, checking travel times for ride shares to your shared workspace, and exploring your immediate neighborhood to get a good lay of the land.
  • If you prepared a must-see list in advance, make sure to add those adventures to your calendar.

Spending this time to get set up to work and meet your immediate needs will help you ease into your workday.

5. Build a digital toolkit.

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 or digital nomad lifestyle. Save the secluded cabin in the wilderness for another time.

Don’t forget these items in your toolkit, too. Conveniences you would have considered normal at home might not be available, but you can minimize the negative impact of not having them.

  • Invest in a VPN for internet security. Carry extra battery packs and chargers, making sure to have plug adapters if you’re in another country with a different type of outlet.
  • Look for screen extenders to replicate that multiple display you have in your at-home office. They’re portable, and some come with stands to elevate the display.
  • If you wear glasses of any kind, have extra pairs in case you lose or break them along the way.
  • Think about your health and wellness while traveling. Plan telemedicine visits with your health care provider and continue to take care of your everyday health. Remember that your domestic health insurance often does not follow you abroad, so if you’re working as a digital nomad in another country, consider Seven Corners Travel Medical Insurance.

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

Your boss (hopefully) approved your trip, so don’t punish yourself for physically being out of the office. There's no need to spend your entire trip working. If you’ve met your goals for the day, close your laptop and enjoy your evening. You are on an adventure, 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 or digital nomad adventure. Contact us with your questions or get a quote online.

Email sales@sevencorners.com

Toll free 1-800-335-0611

Worldwide 1-317-575-2652

Collect 1-317-818-2809


Kylie Stine, Caryn Anderson, and Allison Hache contributed to this blog. Kylie is a former Seven Corners writer, passionate about traveling, music, and ice cream. Caryn and Allison are both professional copywriters whose work has been featured on popular websites such as USA Today, Bankrate, and Credit Sesame.

Search Posts

Newsletter alert

Receive our monthly inspiration and travel tips from the travel insurance experts.

  Sign me up

This website and various social media updates provided by Seven Corners contain content, information, articles, videos, and links to websites created by third parties. Seven Corners, its owners, and its employees neither endorse nor are responsible for the accuracy, timeliness, or reliability of any third-party information, statements, opinions, or advice and are not liable for any loss, harm, or damage caused by your reliance upon them. Use of such information or the linked websites is entirely at your risk. Concerns regarding this third-party content should be directed to the third party. Seek professional advice, as appropriate, regarding your use of such information and websites.

Because the information on this website and in Seven Corners’ blogs and other social media is written and compiled using knowledge and information available at a certain point in time, it may become outdated. For that reason, information, events, legal requirements, and product changes (including benefits, limitations, exclusions, and services) may not be up-to-date, complete, or accurate at the point in time it is being read. Again, use of such information is at your risk.