How to Switch Careers and Find Success as a Digital Nomad

by on Jan 09, 2017 in Careers Remote

When I tell people that I am able to pick up and move (or travel) to any place on earth, whenever I want, the typical reaction is marked by fascination and envy. People curiously ask me, What do you do? followed by You’re so lucky! I wish I could do that…

But I haven’t always been this lucky. Just a few months ago, I was sitting in a cubicle five days a week, from 9 to 5, wishing that I was allotted more than 10 days of vacation a year. Wishing that I had more time to spend with my family and friends, most of whom were a decent plane ride away from me. Wishing that I had the flexibility to work from an open-air coffee shop or a lively coworking space instead of being confined to a claustrophobic cubicle. Wishing that I could travel at the drop of a hat—maybe spend six weeks in Southeast Asia or several months in Eastern Europe…

I longed to find a marketing career that I was passionate about, while having the freedom to work remotely. Call me a spoiled millennial, but  I knew that I couldn’t settle for anything less.

In the end, I found it. And so can you. All it takes is a little perseverance and hard work.

Is This the Right Path for You?

 Before jumping into anything, first consider if this is what you really want. Perhaps you like the normalcy and social camaraderie of working in an office. The digital nomad lifestyle is much more unpredictable and at times, can be lonely. Maybe you prefer the structure and routine that the corporate life provides and the security that comes along with it. As a digital nomad, you will have to create a structured environment for yourself, which requires a great deal of autonomy and self-discipline.

Many people might be fooled into thinking that being a digital nomad is mostly play and travel—and little work. While many Instagram feeds may lead you to believe this is the case, the reality is quite different. Many digital nomads actually work more than traditional 9-to-5 workers. Be careful to assume otherwise.

The human tendency to adopt a “grass is always greener” mentality means that, when we want something that’s just out of reach, we tend to fantasize about the positive things that it will bring, forgetting or not taking into consideration the negative.

The digital nomad lifestyle has innumerable benefits, don’t get me wrong. But it is not for everyone.

To determine if this is the right path for you, start by writing a pros and cons list, comparing the typical office job to one that is location-independent. Get in touch with digital nomads and pick their brains to find out what it’s really like.

Start the Job-Hunt

Once you have determined that you want to be a digital nomad, it’s time to get those job-hunting boots on!

Given the fierce competition and the fact that there are fewer positions available, a remote job is obviously more difficult to find than one that is location-dependent. The good news is that more and more companies, especially those that are smaller and forward-thinking (like marketing agencies), are now hiring remotely. There are even a number of sites out there (like FlexJobs, We Work Remotely, Working Nomads and Remotive) that exclusively post listings for remote-based jobs.

And don’t underestimate the power of social networks—LinkedIn, and even Facebook, are also excellent resources. If possible, change your LinkedIn job title to the title that you want, rather than the one that you currently hold. Recruiters will likely not take you as seriously if you apply for a role that is a complete deviation from your current role. So if you are currently a Proofreader, but are searching for a job as an SEO Marketing Specialist, list your current role as “SEO Marketing Specialist” for “Self.”

Facebook is home to various groups catering to digital nomads, such as the massive “Webworktravel – Digital Nomad Network” group (made up of around 20,000 people) and “Digital Nomads Around the World” (composed of nearly 30,000 people). Not a bad place to start networking! Keep your eyes peeled, because occasionally, job postings are listed in these groups.

Begin Building Your Skill-Set

Being a digital nomad will require a unique type of skill-set. Amidst sending out job applications, hone those skills so that you when you do land that dream job of yours, you will be able to dive right in. Below are some skills that you must adopt as a digital nomad.

Organization: Staying organized is important for any job, but it is essential for digital nomads. Where will you compile all of your notes and how will you organize them? How will you keep track of meetings, deadlines and daily to-do lists? Start thinking about what you can do to stay organized and the apps or programs that will best facilitate your organization.

Autonomy: For all those who have seen the movie Office Space, you surely remember how the main boss, Bill Lumbergh, condescendingly micromanages employee, Peter Gibbons, constantly asking for updates on his work and demanding he be in the office certain days or hours. This is exactly the opposite of what you can expect from the digital nomad work environment. You will no longer have someone looking over your shoulder, monitoring your every move—so start practicing self-discipline and implementing a more autonomous work style.

This can take practice for some. Let’s say you are someone who asks a lot of questions. First, try to see if you can find the answer yourself, before immediately asking someone else. If you perpetually rely on assistance from colleagues when trying something new, try to see if you can do it yourself first.

Time Management: One of the great things about being a digital nomad is having the flexibility to work during the hours that you are the most productive. More of a morning person? Wake up at the crack of dawn and finish work by noon. Work best at night? Explore new cities by day and work in the evenings.

The only downside to this freedom is that sometimes it can be difficult to manage time, especially for those who are used to set office hours and a more structured work environment. To improve your time management skills, start by getting into a routine. Decide when you want to start and finish your work by each day and aim to follow through with that. Define (and prioritize) your weekly and daily tasks and determine how long each task will take to complete. By setting a schedule and forecasting project or task duration, you will be able to manage your time effectively and efficiently.

Focus: Some people can work well in an extremely loud, bustling coffee shop, while others work best in a quiet library. Figure out what kind of environment will allow you to be the most focused and productive. Working independently, you will want to eliminate all distractions, whatever those may be for you. Start to test out different environments and see which one will allow you to stay the most focused.

Communication: Lastly, the key to success for any digital nomad is a transparent communication style. As you will be working and collaborating with people all over the globe, clear and effective communication becomes more important than ever. If you aren’t sure how to do something, ask. After a meeting, repeat the main takeaways. If you are working on a project, provide team members with updates on a regular basis.

At SUCCESS agency, we have developed a system of communication that works well. We all communicate via the application, Slack. Each morning, team members announce their presence by saying “Hello” or “Good morning” to the group. That way, everyone knows who is “in the office.” We also have a range of channels to ensure that communication stays organized and is relayed to the appropriate team members.

Prepare for the Transition

If you are used to the traditional 9-to-5, becoming a digital nomad can be a tough transition. Start reading blogs and forums so that you can best prepare yourself for what’s to come. If you want to move somewhere new, but aren’t sure where, the website Nomad List is a helpful resource. Here, cities around the world are rated based on a range of metrics, such as average cost of living, crime, Internet speed and weather. Consider what factors are most important to you and find the city that best fits those needs. Maybe your priority is to save money, in which case Southeast Asia is probably your best bet. Or perhaps you want to learn Spanish, in which case you might seriously consider South America or Spain. Whichever location you choose, be sure that there is reliable WiFi—after all, this is the lifeline for digital nomads!

Start accumulating a nest egg so that when you land your dream job, you can book that flight to Bali or Copenhagen within minutes.

Connect with other digital nomads. When you go abroad, this will probably become even easier. One thing that I have loved about living abroad is the often-instant connection I make with other expats and travelers. I’ve actually found it easier to meet people and make friends living abroad than I have in the U.S. In a way, it makes sense—We’re all exploring the same foreign land and overcoming cultural barriers. And we all share an insatiable wanderlust.

Finally, learn to be resourceful. While traveling, you will have to improvise on occasion and deal with the unexpected. While traveling, I once used a paper towel as a tea bag, because there was no tea strainer available. Another time, while I was meandering the animated streets of Rio de Janeiro at night, one of the sandals I was wearing suddenly fell apart. Rather than purchase another pair of shoes on the spot (or worse, go barefoot), my friends helped me reconstruct the sandal with a bit of cloth.

Remember that many things will not go as planned while traveling or living abroad—but if you can find innovative solutions to problems as they arise and adapt to any changes along the way, you will surely find success as a digital nomad.

About the author of the post
Mary Blackiston is the Content Marketing Specialist for SUCCESS agency.
  • Nice breakdown Mary. I dig prepping for the transition. Never had to do it; I went from being axed to be a digital nomad LOL. But if making the move more organically you want to plan how to go from employee to globe trotting entrepreneur. If you love fun, freedom and diving into fears, this life is tremendous.


    • SUCCESS agency

      Agreed, Ryan! Best of luck to you! -Mary