Contractor Management 12 min

A guide to freelancing and working abroad

Written by James Doman-Pipe
March 30, 2022
James Doman-Pipe


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The freelancing market has been experiencing explosive growth, and that trend is not showing signs of stopping. Freelancing offers a wide range of benefits and opportunities, including the flexibility of working travel options. In many cases, if you want to freelance, you just need a device to work on and an internet connection. As long as you have the right work permits and you can stay on top of the taxation ramifications of the digital nomad lifestyle, there’s not much stopping you from seeing the world while you freelance.

Freelancing abroad is very different from more traditional jobs. Aspiring international freelancers should invest time in researching what’s required to manage this lifestyle effectively and maintain productivity.

It’s also important for potential business partners to be aware of how to manage their agreement with an international independent contractor. The dangers of contractor misclassification can cause catastrophic problems for these business relationships if not managed effectively.

Benefits of freelancing and contracting internationally

The major benefits of freelancing include flexibility, independence, and opportunities for change and growth. Freelancers can choose when and how to work. That means more control over your lifestyle and more capacity to spend time with friends and family when it suits you.


When you freelance you can work from virtually anywhere as long as you have a few simple tools. You’ll likely need an internet connection and an appropriate electronic device. This means you have a lot of choice for the way you work and where you choose to do so. You can work while you travel, you can work from a co-working space, a cafe, a hotel, or on top of an airplane tray table.

Additionally, freelance work can afford you the opportunity to adjust your work schedule to your liking. This can allow you to make your work schedule more compatible with other obligations and your lifestyle.

Flexibility is particularly important in an increasingly globalized culture and economy, which allows for a greater range of opportunities related to things like travel, professional relationships, and personal enrichment. The benefit of flexibility can even help freelancers weather significant changes in their lives, such as necessary relocation.


While you will have to abide by any contractual agreements you make, freelancing allows you to operate as your own boss. As such, you will create your own policies, build your own schedule, determine what products or services you will offer, and decide how much to charge. While you might have less certainty than full-time employees, you’ll be in control of your workload and your time.

Opportunities for change and growth

As mentioned, when you freelance, you make the calls. If there is anything you don’t like about different aspects of your day-to-day work, you can make adjustments. For example, if you don’t like how often you are working, what type of work you are doing, or what type of client you work with, any changes you want to make are in your hands.

You can also delve into different career paths and determine how you might like to expand your business if at all. Freelancers associated with a company may even be able to experiment with longer term contracts and receive compensation for remote work. This allows both parties to generate an understanding of how best to work together with the option to transition to a full-time employee agreement if desired.

Visas and work permits

You may need to obtain a visa or work permit to travel while you work, depending on many different factors specific to each situation. These factors may include things like your country of origin, the type of work you are doing, and your background. Different countries will have different requirements related to granting permission for foreigners to enter the country.

Make sure you investigate the specific credentials required for you to work legally in whichever jurisdiction you are traveling into before you start your trip.

It is also important to note that freelancing and self-employment are sometimes defined separately from other types of work considered for visas. The following are a few visas commonly used by international freelancers.

Student visas

Before we outline the details of student visa requirements, note that freelancers should only pursue this visa if education is demonstrably a primary priority and freelancing is secondary. If you have side hustle or part-time contracting work, you may still be legally qualified with a student visa, but you can run into trouble if your work is deemed to be your primary focus.

This type of endorsement allows foreign students to study at the educational institutions of another country. A student visa can be a great option for freelancers who are also going to school. Special considerations that apply to international freelancers include:

  • Many student visas only allow for part-time work.

  • Some student visas may not allow you to work at all.

  • Some student visas may not allow you to work for a certain period after arrival.

  • Some student visas may only allow you to do certain types of work, such as on-campus opportunities.

Due to the possible restrictions, it may be best to only pursue this type of visa if your education abroad is your priority above work.

Work visas

Work visas allow foreigners to reside in a country without citizenship due to employment opportunities available in the country. This may be available for a limited or indefinite period and you must ensure you have the legal right to perform any sort of work in the country (even freelancing for yourself).

The specific requirements for obtaining a work visa depend on the country, and freelancers may not be eligible. Special considerations that apply to international freelancers include:

  • It is often difficult to obtain a work visa without sponsorship or employment from a large, well-established company within the country.

  • It may be helpful to form your own company within the country (but this comes with it’s own costs, risks, and time investments)

  • This option may be particularly tedious and present many legal obstacles

  • You also introduce a suite of new taxation obligations if you choose to start your own company in another country

Overall, obtaining a work visa is often not the most feasible for freelancers who are not already closely affiliated with a company within the host country.

We want to emphasize the point above. Obtaining a work visa is not a simple ask and receive process. If you don’t have the legal rights to work, you are risking serious fines and penalties. Make sure you have the right work visas and permits before you leave for a so-called working holiday.

Use our Contractor Compliance Checklist to avoid misclassification

Work through this checklist to help determine if a new hire should have a contractor or employee relationship.

A tablet with the title contractor compliance checklist.

Why more companies are hiring internationally for remote and contract work

For companies, the benefits of hiring internationally for remote and contract work include:

  • An expanded pool of talent to choose from

  • Opportunities for diverse insights

  • Ability to fulfill inconsistent labor needs

  • Opportunities for engagement with ambitious talent

This demand is catapulting remote freelancing opportunities for professionals around the world.

Helpful guides for freelancers and digital nomads

Here are some additional resources that will help international freelancers and businesses working with remote contractors:

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Freelance visas

Some countries offer freelance visas, which may be a helpful option if you do not qualify for other types of permits or visas. These visas typically offer a limited window for freelancing within the country. Special considerations that apply to international freelancers include:

  • Freelance visas also may be called self-employment or entrepreneur visas.

  • As a relatively new development, relatively few countries offer this type of visa.

  • You may need to provide proof of minimum income.

List of countries across regions that are currently offering a digital nomad visa:

North America:

  • Mexico

Latin America:

  • Aruba

  • Anguilla (UK Territory)

  • Antigua and Barbuda

  • Bahamas

  • Barbados

  • Belize

  • Bermuda

  • Cayman Islands

  • Costa Rica

  • Curaçao

  • Dominica

  • Montserrat

  • Panama

Europe, Middle East and Africa:

  • Cabo Verde

  • Croatia

  • Czech Republic

  • Estonia

  • Georgia

  • Germany

  • Greece

  • Iceland

  • Malta

  • Mauritius

  • North Macedonia

  • Norway

  • Portugal

  • Romania

  • Seychelles

  • UAE


  • Australia

  • Indonesia

  • Malaysia

  • Taiwan

  • Thailand

More countries may introduce these visas to incentivize digital nomads as freelancing continues to grow in popularity.

Travel visas

A travel visa allows you to visit a country for a specified time for either personal or professional reasons. This can be ideal for freelancers who are planning short-term visits to another country.

Note that most travel visas do not give you the legal right to work in the country.

Legislators and taxation departments are focusing more and more on compliance in this area as the transition to remote work intensifies and digital nomadism becomes more mainstream. This means you are now more likely to be caught if you are working without the correct visa or permit.

Special considerations that apply to international freelancers include:

  • Some countries may not allow you to work during your visit.

  • While travel visas are often granted for a very limited time, some countries allow for extended stays.

  • Some countries offer a “working holiday visa,” which is offered to young adults to allow them to visit the country while simultaneously working to fund the trip.

To obtain a travel visa, you will often have to indicate whether the reason for your travel is primarily for leisure or business purposes.

Taxes at home and abroad

Freelancers spending time abroad may be subject to unique tax obligations, depending on factors such as their business model, the type of work they will be doing, and what their origin and host countries are.

It is important for both the freelancers themselves and businesses that hire independent contractors abroad to be aware of the unique tax considerations that may be involved in this scenario.

A few unique considerations may include the following:

  • Most countries will require you to pay taxes while you reside there, regardless of the length or nature of your stay

  • Most countries do not require their citizens to continue paying taxes while staying abroad, however, some (notably the United States and Eritrea) still require their citizens to pay taxes while abroad

  • You will have to fill out any relevant tax forms related to your income and your foreign status

  • You will likely have to pay self-employment taxes and you may be eligible for deductions related to work-related expenses like space and materials.

  • An extended stay abroad may put you at risk for permanent establishment which carries significant tax ramifications

Relevant taxes and deductions vary widely depending on the host country, and therefore you must be aware of relevant tax regulations before you begin work in a new country, even as a freelancer.

Staying connected

A reliable internet connection is vital for many freelancers, and travel can be a complicating factor in that regard. Connection speeds and coverage vary depending on the area, and some mobile devices may be more reliable than others. It is also possible for circumstances such as poor weather to impact service.

Therefore, it is important to be aware of potential coverage issues or complicating factors before you go abroad. Meanwhile, businesses who partner with independent contractors or freelancers should ensure they understand how connectivity may impact their ability to manage the professional relationship.

Finding jobs

There are many different ways to find a remote freelancing job. These options include:

  • Word-of-mouth from existing clients

  • Online job boards

  • Online freelancing platform

  • Online forums related to your professional skills

  • Newsletter subscriptions

It is also often helpful to simply tell people what you do and that you’re looking for work.

link to What is remote work? Remote work handbook [2022]

What is remote work? Remote work handbook [2022]

The complete handbook to remote work by Remote, where you can learn everything about what Remote work is, as well as advanced remote work tips, tactics, and guides from the experts.

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