The world is changing, and advances in technology, insights into employee productivity, and certainly Covid have served as catalysts for significant paradigm shifts around how and where people choose to work. 

People are seeking remote work in order to increase their well-being, have more family time, and improve their work-life balance.  Companies, big and small, are supporting remote workers globally as well.  Pursuing these workers allows businesses to save on costs and overhead while enjoying greater employee productivity.

Even governments and countries are endeavoring to attract digital nomads, in order to gain economic benefits through taxes and local consumption, while also giving a boost to innovation. As a result of this big shift, career opportunities and options to work remotely are increasing.  There are job openings for people with little or no experience, high school to advanced degrees, and across all job sectors and industries. 

We have been digital nomads for a long time and work remotely in countries and settings around the world. We love sharing helpful tips, tricks, and resources on how to pursue a nomadic lifestyle of working while traveling and seeking adventures.

Here is some helpful information and considerations to support you on your way to becoming a digital nomad… 

Self-Employed

Employee Versus Self-Employed

The first threshold question you need to consider on your road to becoming-a-digital-nomad, is do you want to be an employee or self-employed?  Would you prefer to work for someone and be part of a company, or would you rather be your own boss as an entrepreneur or freelancer?

Here is a look at some of the pros and cons of each model… 


Pros of Being an Employee

Predictable work- As an employee, you know what is expected of you and understand your duties and workload.

Predictable income- Your income and salary are known quantities and you receive a consistent paycheck. 

Benefits- Health benefits, company stock, holidays, and sick pay are available.

Taxes- You do not have to manage estimated taxes, self-employment, or other tax-related costs.


Cons of Being an Employee

You have a boss- You are beholden to someone and could have challenging personal dynamics.

Schedule- You are expected to maintain a schedule and may have meetings and events that interfere with your life or travel.

Dependent- you are dependent on a company to determine how much money you make and the direction of your career.


Pros of Being Self-Employed

You are your own boss – The only person you are accountable to is YOU

Passion – Allows you the option to pursue a field or endeavor you are enthusiastic about.

Flexibility – You are in complete control of when and how you work, as well as what projects or tasks you decide to pursue.

Save on expenses – Saving on costs like work clothes, cars, and gas for commuting, as well as housing in expensive urban areas.

Personal dynamics – You are in control of who you work with.

Earning potential – The sky is the limit to how much you choose to work and earn. 


Cons of Being Self-Employed

Inconsistent income – Unpredictable earnings can be stressful, especially if you don’t have money in savings.

Sourcing your own work – This can take up considerable time and effort and needs to be factored into your time management. 

No benefits, retirement plans, or paid vacations- Although there are a lot of great travel insurance options (see our resources page) you will have to source this on your own and plan your own retirement savings.

Isolation – Some people prefer working with other people and can find the solitary nature of remote work uncomfortable.

More paperwork – Instead of your employer handling the paperwork involved with having a job, you are required to manage taxes, permits, visas, etc.

We personally prefer being self-employed and find it works well with our nomadic lifestyle and living internationally.  However, I know many people, both personally and professionally, who don’t like the uncertainty and unpredictability of self-employment and choose to be an employee.  Both models can work very successfully while being a digital nomad and there are thousands of jobs available for each type of remote work.

Working remotely

Best Digital Nomad Jobs for Employees

If you are going to be an employee here are some of the best and most coveted jobs that are conducive to remote work:

Web developer – Responsible for designing and building websites that are both functional and enjoyable to use. This can be a great career for people who like both the technical side of things, but also enjoy putting their creativity to work.   Businesses of all sizes, across the world, are looking for developers and this is a career that has strong job security.

Software engineer – This is a job you can do anywhere in the world and it is a field that is growing rapidly!  Engineers create code that allows for high-functioning systems and improves and expands upon existing ones.  You can do it from anywhere in the world if you have a reliable computer.  

Cyber security – This career recognizes problems by identifying violations or abnormal functioning in systems. Security specialists define access privileges, resources, and control sequences and structures. Companies and organizations are always looking for individuals to help them protect valuable data.  

Social media and marketing- As a social media manager you work to expand a company’s reach by creating and implementing great digital assets and content.  You may use Instagram, Facebook, Twitter, Pinterest, or YouTube and need to stay up to date on the latest social media trends.

SEO Strategist- SEO is skill companies need in order to grow their online presence. You need to know how to interact with websites and be familiar with how content appears in search engines.  There is a high demand for these jobs, and you can do it from any place on the globe!


Best Websites for Finding Remote Work as an Employee

A few suggestions when beginning your search on a job search website…

  • Get a strong resume in order…this way when you find a position that looks interesting you can submit it right away.

  • Use the filters in your job search to choose remote work.  This will allow you to immediately see the jobs available to those seeking remote positions. The filters also allow for things like choosing education and experience level, type of work, and part or full-time.

  • Browse all the remote jobs even if you think you know what field or type of occupation you are looking for.  Oftentimes people find careers that they previously would not have considered, just by looking through a variety of openings. 

  • Be honest and upfront with your employer if you are going to be nomadic or traveling while you work,   Most companies are perfectly fine with nomadic employees, so long as the work is getting done at a high standard!


There are dozens of websites that are excellent resources to find and source remote work.  Here are a few of the main ones:

Indeed A global employment site with over 250 million users each month!  The site allows companies to post jobs and they have a wide array of industries to choose from.  

Glassdoor– A sizeable and free job search engine.  Glassdoor has good reviews of companies, which helps you get an idea from real people of the company culture.

Linkedin A large networking platform that can be useful when looking for a new career.  It does require a fee for a premium account that has access to more coveted features.  

Monster– A great company for connecting job seekers and employers.  Salaries are sometimes not included in postings, but jobs can be easily filtered with keywords.


Best Digital Nomad Jobs for the Self-Employed

If you are going to be self-employed or a freelancer here are some of the best and most exciting jobs to pursue…

Coaching – This is an industry that is exploding as people seek support in various areas of their lives. There are coaches for business, personal well-being, and careers, to name just a few. There are dozens of books and coaching programs you can sign up for to help you develop your niche.

Teaching – This is a job that is sought after across a multitude of settings, industries, and countries. There are companies, schools, and individuals looking for teachers in English, math, sciences, and the arts both online and in person.

Graphic designer – Companies and individuals are looking for help with logos, branding, marketing, and advertising.  

Copy editors and writers – There are thousands of companies looking for writers and editors across a multitude of industries.  Individuals are responsible for editing content, creating posts, and correcting copy.

Medical transcriptionists – This is a no-experience-needed position that requires a person to convert voice recordings from physicians and healthcare workers into formal reports  Transcriptionists may also edit medical records for accuracy and return documents for review and approval.

Blogger – If you have a passion for something and want to write and share what you know you can create your own blog to share your knowledge and enthusiasm. 


Best Websites for Finding Remote Jobs for the Self-Employed 

Here is a list of excellent websites that connect freelancers, entrepreneurs, and individuals looking for remote work across a variety of industries.

Upwork – I personally use Upwork almost every day!  They have a global reach connecting businesses with independent professionals and agencies around the world.  I have worked with graphic designers, google experts, tax attorneys, and website developers. 

Jooble – An enormous search engine for job seekers that operates in over seventy countries. The site has a very user-friendly platform.

Flexjobs – A resource for job seekers who are seeking high-quality, remote jobs. There is a small subscription fee that is well worth the expense. 

Fiverr – An online marketplace for freelance workers and businesses. There are jobs in translation, graphic design, video, and programming to name just a few.  

Friends and Family- Make sure you use your own personal network to spread the word about the work you do and your availability.  Send out an email to everyone you know and ask them to circulate and share on your behalf. 


Inspirational Work Stories from Digital Nomads

Here are a few stories from my friends, family, and clients, and how they made the transition to work remotely and follow their dreams…

Dave from San Francisco 

Dave is a thirty-five-year-old successful insurance advisor was feeling burnt out and craving more balance.  He decided to pursue a life filled with more nature, surfing, and family time.  He and his wife, along with their two toddlers liquidated their apartment in San Francisco and moved to Costa Rica.  For the first year, he continued to consult for the insurance company remotely, while also pursuing his passion for writing short story fiction.  He eventually quit working with the insurance company altogether, and now sells his short stories online. His toddlers are fluent in Spanish, and his wife works in the preschool that they attend three times a week.

Jamie from Galveston

Jamie, a forty-year-old family physician from Galveston, uninspired by the day-to-day realities of her career, moved to Portugal (a great country for digital nomads!) to shake things up and experience a different reality.  Not legally allowed to practice medicine in a different country, she is now consulting with teams of doctors all over the world on how to set up successful medical practices. She is living in a top-story flat, with beautiful views of Lisbon, and has made some of the most meaningful friendships of her life.   

Erika from Bend

Erika, a recent high school graduate wanted to travel while she sorted out her college and career aspirations and plans.  She applied to positions on several au pair placement sites and landed a job with a wonderful family living in Croatia.  She helps take care of three kids while traveling with the family. She not only receives a great salary but has free room and board and is able to travel on holidays and weekends. 

Angel from San Diego

Angel, a 28-year-old fitness fanatic was sick of her corporate job in medical sales.  She pursued a personal training certification, after studying for two months, and now teaches exercise classes online while backpacking and hiking all over the United States in her sprinter van.  She tripled her hourly rate and sets up her workout studio with a new scenic backdrop every few weeks…which her clients love!

Seth from Palo Alto

Sepp, a fifty-year-old tech executive, at one of the biggest corporate companies in the world, asked if he could work remotely full-time.  His company agreed to the arrangement, so long as he returned to Palo Alto twice a year for the company retreats.  He rented out his house and moved to Italy to pursue his passion for cooking.  He cut his California overhead expenses in half and has met all sorts of amazing new friends through his cooking classes.  


Life is short and the world is big, make the jump!

I share these stories because I hope it allows you to see yourself in some of these examples.  No matter your age, place in life, education level, or work experience there is a path forward and opportunities to work and travel. Most of the people mentioned above had little to no savings, and every single one of them reduced their overhead and expenses!

It is important to remember that you don’t have to have everything figured out before you go. In fact, one of the best parts of the adventure is to sit in the unknown, trust that you will determine the best path forward and you will learn about yourself and what works best through trial and error. 

I wish you much success in your pursuit!  Let us know your story!


Explore visa-friendly havens for digital nomads. Discover the perfect blend of work and wanderlust in these top destinations. Your passport to productive adventures awaits!

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