Contractor Management — 9 min
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.
In this guide, we explain how you can work as a freelancer, land well-paying remote jobs, and manage your taxes both at home and abroad. We also look at what you need to know about visas and work permits when working freelance.
Freelancing is a form of self-employment in which individuals offer professional services to clients. Freelancers are independent contractors who manage their day-to-day schedule and choose who they work with. They’re typically paid through hourly contracts, project-based work, or retainer agreements.
If you become an independent contractor, you must find and manage your own clients. That also means taking care of the administrative tasks that an employer would normally handle — negotiating contracts, invoicing clients, and handling taxes.
Freelancing can be rewarding, but it’s certainly not for everyone. Working as a freelancer is right for you if:
You value flexibility and independence.
You enjoy managing your own schedule.
You have strong communication skills.
You’re adept at handling multiple projects.
You’re a self-driven and highly motivated individual.
The freelancing market has been experiencing explosive growth, and that trend is not showing signs of stopping. Data shows an estimated 86.5 million people in the US will be freelancing by 2027, making up over half (50.9%) of the total US workforce.
Freelancers work in different fields, but some of the most common ones include:
Accounting: Thirty-nine percent of small business owners say one of the top challenges of growing their business is managing their finances and accounting. You can work with businesses to manage their bookkeeping and help them stay financially healthy.
Customer service: If you enjoy working with people, you could help businesses answer phone inquiries and troubleshoot customer issues.
Education: The education field offers plenty of flexible work options. As a freelancer, you could work one-on-one with students, help with curriculum planning, create online courses, and more.
Marketing: Nearly a quarter of small businesses (22.8%) indicated lead generation as a top marketing challenge. Freelancers often work with businesses to create and manage campaigns for SEO, social media, and content marketing.
Software development: Software developers can offer mobile app development, software testing, and application maintenance services.
More people are transitioning away from traditional work. An estimated 83% of freelancers who have already taken the plunge say the biggest benefit was being their own boss. Of course, this isn’t the only reason why workers are striking out on their own.
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. 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 create your own policies, build your own schedule, determine what products or services to 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.
When you freelance, you make the calls. If there’s 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.
Before you jump into freelancing, it’s important to consider the drawbacks. These include:
No employee benefits: Freelancers don’t receive the benefits that come with traditional employment (e.g., health insurance, paid leave, stock options, etc.)
Challenges in finding clients: As a freelancer, you need to find new clients and continuously market your services to maintain a steady workload.
Experiencing “feast or famine” cycles: Sometimes, you may have periods of too much work (feast) or little to no work (famine).
Maintaining a healthy work-life balance: Freelancers may struggle to separate their personal and professional life.
Dealing with isolation: Freelancing doesn’t have the same social interactions that come with traditional workplaces, which can lead to freelancers feeling isolated.
Despite these drawbacks, freelancing can be a rewarding and fulfilling career choice. Let’s look at one of the top challenges that freelancers face — finding work.
Becoming your own boss is an exciting prospect. But it comes with a learning curve, especially when you’re just getting started.
Follow these steps to find (and land) a well-paying freelancing job.
The first step is to determine what services you’re going to offer. You have a few options here:
Leverage your existing skills: If you already have some work experience, there’s a good chance you can leverage your current skills to transition into freelancing. If you’d rather work in a different field, you can also find a niche based on your interests.
Develop expertise in in-demand skills: Another option is to develop skills based on what’s in demand. For example, as the AI market experiences explosive growth, you could develop AI-related skills and pursue freelancing jobs in this field.
As you determine your offerings, consider specializing in a niche within your field to position yourself as an expert and establish credibility.
Determining your rates is a fine balance — charge too little and you risk undercutting yourself (and burning out) but charge too much and you may find it difficult to attract clients.
Common ways to price your services include:
Hourly pricing: This model involves setting an hourly rate. For example, you could charge clients $40 an hour for bookkeeping services.
Project-based: With this model, you charge clients a fixed rate for a project. For example, you might charge a flat $500 to design business logos.
Value-based: This pricing model involves charging clients based on the value of the outcome delivered. If you’re a marketer, you could charge clients a fee based on a campaign’s impact on their revenue.
Consider your level of expertise, the complexity of a project, and current market rates for similar services when setting your rates.
To land new clients, you need to demonstrate you’re the right person for the job. A good place to start is to build a portfolio — a “resume” that contains a collection of your work. It helps you showcase your expertise, build your personal brand, and attract potential clients.
If you’re a new freelancer you might not have anything to put in a portfolio. Ways to build relevant experience include creating personal projects, offering to work for free, and working at discounted rates. Publish pieces on platforms like Behance to showcase your work. However, be sure to get permission from your clients before publishing their materials.
There are many different ways to find a remote freelancing job. These include:
Word-of-mouth from existing clients
Online job boards like Remote for Jobseekers
Online freelancing platforms
Online forums related to your professional skills
Newsletter subscriptions
Of course, other freelancers are using similar methods to find work. Make sure to create compelling proposals to stand out. They should be tailored to each client and highlight how your skills can help them achieve their goals. Even after you land a few great clients, it’s important to continuously market your services to keep your freelancing career thriving.
As a freelancer, you’re essentially a business owner. This means the administrative aspects of running your business fall on you.
Make sure to manage your day-to-day operations well. This includes:
Tracking your income and expenses
Managing contracts
Invoicing your clients
Managing your schedule
Preparing your taxes
Working with clients in other countries?
Remote’s Freelancer Hub lets you create locally compliant contracts, receive payments in your preferred currency, track billable hours, and more.
Freelancers are considered self-employed, so you’re responsible for paying self-employment taxes, which is 15.3% — 12.4% for Social Security and 2.9% for Medicare. Note that you may need to file estimated taxes on a quarterly basis throughout the year. Consult with a tax professional to ensure you’re meeting your tax obligations.
It depends.
You may need to obtain a visa or work permit to travel while you work, depending on different factors. These include things like your country of origin, the type of work you’re doing, and your background. Different countries will also 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 travel into before you start your trip. It’s 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.
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 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 its 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 risk serious fines and penalties. Make sure you have the right work visas and permits before you leave for a so-called working holiday.
Work through this checklist to help determine if a new hire should have a contractor or employee relationship.
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.
Here are some additional resources that will help international freelancers and businesses working with remote contractors:
The Ultimate List of Freelance Visas for Remote Workers: This lists notable freelance visa opportunities available in various countries.
Expert guide to hiring independent contractors abroad: This guide helps business owners and hiring managers protect their company when hiring independent contractors abroad.
Travel Advisories (U.S. Department of State): This database allows you to search your intended destination and learn about any relevant notices that may impact travelers.
How to work with remote contractors: This is a comprehensive guide for businesses interested in partnering with remote contractors.
How to offer benefits for 1099 and international independent contractors: This article provides advice on developing competitive benefits packages for independent contractors.
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
Asia-Pacific:
Australia
Indonesia
Malaysia
Taiwan
Thailand
More countries may introduce these visas to incentivize digital nomads as freelancing continues to grow in popularity.
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.
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.
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.
If you’re starting out, freelancing can seem overwhelming. The good news is you don’t have to go it alone. Remote’s Freelancer Hub can help streamline your work and make your life easier. Easily manage your clients, create locally compliant contracts, and send invoices — all from one place.
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