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Remote work is a privilege

8 Ways to Thrive as a Digital Nomad, According to Springboard Experts  

9 minute read | October 17, 2023
Kindra Cooper

Written by:
Kindra Cooper

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For many career switchers, one of the most tantalizing prospects of a tech career is the remote work privileges. Location independence and schedule flexibility liberate tech workers to blend their work and personal lives, avoid stressful commutes, and, in some cases, explore the world. According to Velocity Global, 72% of tech companies have employees working outside a company-owned office.

A few years after starting her own UX design consultancy, Vitamina K, Karla Fernandes, a mentor for Springboard’s UI/UX Design Bootcamp, sold all her belongings and terminated the lease on her apartment in Sao Paulo, Brazil. She was left with two suitcases, a one-way ticket to Buenos Aires, and an open mind. Now, she’s established a new home base in Switzerland but frequently travels to meet her clients worldwide. 

“The biggest opportunity I’ve had from becoming a digital nomad is understanding different cultures and how UX design standards vary from country to country,” says Fernandes. 

The Pew Research Center found that 35% of U.S. workers with jobs that can be done remotely work from home full-time, compared to a 55% peak in 2020. 

 “I dislike the corporate life; I want to have the freedom to work wherever I want,” says Hamza Al-Husseiny, a mentor for Springboard’s Data Analytics Bootcamp. He travels mainly between Dubai and his hometown of Cairo. “Mind you, being a freelancer puts a huge responsibility on you to be your own boss,” he adds.

The lure of digital nomadism is growing stronger as remote workers seek to leave expensive, crowded city centers in search of increased square footage or the opportunity to jetset. A recent survey by Upwork found that 28% of respondents intend to move more than four hours away from their current residence. 

If you’ve been contemplating becoming a remote worker, here are some tips on how to blend full-time work and full-time travel.

1. Find a fully remote job

Before booking a one-way plane ticket, make sure your job is truly remote. Some companies allow staff to work from anywhere unconditionally, while others restrict time abroad. Airbnb, Hubspot, and Shopify permit full-time employees to spend 90 days out of the country, while Google’s limit is 28 days. Small companies are twice as likely to hire full-time remote workers, according to a State of Remote Work report by Owl Labs, to save money on office space. “Remote-first” companies like Dropbox, GitLab, and Stack Overflow have lenient remote work policies, and some even provide a WFH stipend for a home office. 

Remote jobs give flexibility to remote workers

With return-to-office mandates dominating headlines, job seekers are increasingly hard-pressed to find a truly remote job and ensure employers won’t turn the tables once they sign on the dotted line. 

She advises being upfront with an employer during the job interview if you plan to travel while working remotely. 

Some questions to ask a prospective employer include:

  • Is there a daily standup meeting?
  • Is communication synchronous or asynchronous?
  • What are my work deadlines? Are they subject to change?
  • What are the rules for working from a different timezone? Do I have to be available during regular business hours?
  • Do I need to tell HR if I plan to travel outside of the country for an extended period of time? 
  • Does the company have a formal remote work policy?  

“Unless it’s written in your contract, you do not need to tell your employer if you’re leaving the country,” says Fernandes. “A lot of companies measure employee efficiency through tests. As long as you pass those tests, meet deadlines, and deliver what you promised, that’s what matters.”

Another consideration is what career stage you’re currently in. If you’re in an entry-level position or recently switched careers, you might benefit from the interactivity of an office. 

“I usually advise my mentees to go to the office for the first five years of their career, even if it’s just a couple of days a week,” says Chinua Katchy, a security operations analyst at Algolia and a mentor for Springboard’s Cybersecurity Bootcamp. “You might need some guidance and handholding, and it’s easier to ask your teammates for help when you’re in an office.” 

2. Decide where to go

Deciding on a destination can be daunting, especially when planning a multi-year itinerary. Travel planning for work purposes is very different from vacation planning. Consider how timezone differences might impact your working hours. If your employer expects synchronous communication (eg, the response time for a Slack message is one hour or less), this could throw off your sleep schedule or ability to go sightseeing outside of business hours. 

“When you travel as a digital nomad, you’re essentially looking for a place to live,” says Al-Husseiny. “You want to find an affordable place with a reliable internet connection and service infrastructure to support you.” 

Remote work travel planning

Access to public transportation, shared workspaces, and high-speed internet are essential to staying on top of your workload while giving yourself time to see the sights. Consider factors like weather, safety, and leisure activities. Is it easy to meet other digital nomads? Is there an active expat community? How much of a language barrier can you tolerate? 

“I would also consider whether or not I speak the local language,” says Fernandes. “When I went to Turkey and Istanbul, I knew there were a few internationalized towns where everyone spoke English.”

If you’re planning an extended stay beyond what a tourist visa allows, look for countries that offer visas for remote workers. Al-Husseiny has set his sights on Malaysia as his next travel destination. Malaysia’s DE Rantau Nomad Pass is valid for 3-12 months, with the possibility of an extension. Minimum income requirements are only $24,000/year, given the country’s relatively low cost of living. Forty-nine countries offer “workation” visas, including The Bahamas, Barbados, Costa Rica, Germany, Iceland, Norway, and Portugal. Each country has a specific name for the visa. Research your target destination thoroughly before jetting off. 

Also, consider the strength of your passport. Certain passport holders can travel without a visa or obtain a visa-on-arrival (VOA). For example, U.S. citizens can stay in 148 countries without a visa for 30-180 days. 

3. Get your finances in order

Working remotely doesn’t have to break the bank. Some countries may even offer a lower cost of living than your home country. 

“I’ve never spent more than $1,500 a month, including travel costs and accommodation,” says Fernandes, who has spent the last seven years traveling. “If you don’t need to live like a king, you can live well on a budget.”

Remote work travel budget

Budget for your living expenses, from rent to food and entertainment. Do you plan to lease an apartment, rent an Airbnb, stay in hostels, or couch-surf? Will you rent a coworking space or vie for seating at coffee shops? Calculate your living expenditures, the cost of traveling to each destination, the activities you’ll do there, transportation costs, and how it will affect your savings. 

“If you’re paying a mortgage back home, becoming a digital nomad is risky,” advises Al-Husseiny. “When you travel to a new country, you won’t have as many connections or know the best places to get new gigs.”

If you’re a freelancer, ensure you have a steady stream of work to help cover your travel expenses. Also, make a contingency plan if work dries up while you’re backpacking in Uruguay.

 “Ask yourself how long you’ve been in your field; if you’ve only freelanced for a year or two, traveling is risky,” says Al-Husseiny. “But if you are established and have many clients, you have more confidence in choosing where to go.”

Finally, consider how much cash, if any, you’ll need to carry. While most major U.S. cities are cashless, rural merchants won’t accept credit cards, debit cards, or digital wallets. Withdraw cash from an ATM when you arrive at a new destination, if necessary. 

4. Know where and how to pay your taxes

Whether or not you pay taxes outside of your home country depends on how long you stay there and what type of visa you’re on.  The UK, Canada, and Australia consider a stay of 183 days as grounds for tax residence status. U.S. citizens must file U.S. tax returns regardless of where they live. 

Digital nomads pay taxes in their tax residence country (your permanent physical address), home country (country of citizenship or permanent residence), or both. Your employer may need this information to file payroll taxes.

Here are some important tax considerations for digital nomads: 

  • Determine tax residency. Research your destination country’s rule for tax residency and decide how long you plan to stay. Also, consider how your digital nomad visa affects your tax situation. Some countries offer tax breaks to incentivize remote workers to relocate there. 
  • Understand foreign income rules. It’s crucial to understand how foreign income is taxed in both your home country and the countries where it is earned. Some countries have double taxation treaties to prevent you from being taxed on the same income twice.
  • Research tax treaties. Familiarize yourself with tax treaties between your home country and the countries you plan to visit or reside in. These treaties can provide guidelines on which country has taxing rights over specific types of income.
  • Keep detailed records. Maintain documentation of your income, expenses, and travel history. Proper documentation is essential in case of audits or inquiries from tax authorities.
  • Consider tax-friendly countries. Monaco, Andorra, and Switzerland have low or zero-income tax rates for digital nomads. 

5. Find the right accommodation

Traveling while working puts some restrictions on where you can go. While staying in a central location costs more, it might benefit your work/life balance, making it easier to go on adventures before or after work hours. 

While working remotely from Ibiza, Katchy brought his laptop to the beach to write code. “Thankfully, my apartment was close to the beach, so when I had a meeting, I would rush back to my apartment and then go back to the beach when it was done,” he says. 

Here are some tips for finding accommodation when working remotely:

  • Make sure you have a workspace. Look for lodging near a coworking space, coffee shop, or public library. Ensure your Airbnb, hotel, or apartment has a comfortable workspace—a desk and ergonomic chair—if you need to take meetings in a quiet location. 
  • Find discounts for long-term stays. Check with your hotel, AirBnB host, or landlord regarding discounts for extended stays, such as weekly or monthly rentals. 
  • Get kitchen access. Access to a stove and refrigerator lets you save money and eat healthily.
  • Scout the location. Consider proximity to grocery stores, cafés, gyms, and public transportation.

6. Get travel health insurance

Travel health insurance can reimburse you for unexpected emergency medical costs and safeguard your nonrefundable reservations/trip cancellations if you fall ill and miss a flight. Make sure you buy a health insurance plan that’s valid in all the countries you intend to visit. However, if you relocate abroad for an extended period and don’t intend to travel for a few months, international health insurance may be a better option. 

7. Connect with other digital nomads

Remote work can be lonely and isolating, especially when traveling to uncharted places where you don’t know anyone. Summering in a rural village in Romania might sound romantic, but a lousy internet connection could jeopardize your employment. If the nearest city is a two-hour bus ride away, your ability to meet people and take in tourist attractions dramatically diminishes. 

Remote work communities exist around the world to help digital nomads meet each other

International digital nomad communities like Couchsurfing and NomadList will help you meet other remote workers. You can also join local Facebook groups and Meetups for digital nomads. The Nomadbase Facebook group has over 67,000 members. 

Alternatively, find fellow tech workers on LinkedIn and tell them when you plan to be in their city. 

“I use social media to find other people in my field and meet them in person,” says Katchy. 

8. Set realistic expectations

That vision you’ve always had of working from the beach while sipping from a coconut? You might do it once or twice for the sake of your Instagram reel, but it’s ultimately impractical. 

“Beaches have a lot of moisture and sun, which are not good for your laptop,” Al-Husseiny warns. “Also, the Wi-Fi connection is not good, even if you’re using an external mobile hotspot.”  

Moreover, digital nomadism requires a penchant for planning ahead and iron-clad self-discipline. 

“When I travel, I want to do a lot of sightseeing during the day, but that’s also when I have to work,” says Katchy. “You must realize you’re not on vacation and still need to get your job done.” 

About Kindra Cooper

Kindra Cooper is a content writer at Springboard. She has worked as a journalist and content marketer in the US and Indonesia, covering everything from business and architecture to politics and the arts.