The Top 5 Things One Should Know About Being a Digital Nomad

I caught the travel bug back in 2012 when I took my first airplane ride ever to the island of Palawan in the Philippines.  Having the ability to see a new place while meeting interesting people opened my eyes to the excitement that traveling offers.  Since then, my need to travel has only continued to grow.  


I’ve been fortunate enough to build a unique lifestyle around remote work that gives me the flexibility to travel as much as I want.  This has allowed me to see a lot of the world without the worry of begging a boss for PTO (Paid Time Off) or limiting the amount of time I can travel each year.  I've swam with whale sharks, gotten a tattoo from a tribe of head hunters, taken selfies with monks, traveled by bus for 30 hours straight, and had many other unforgettable experiences around the globe.  


This is all thanks to my work as a freelance writer and digital nomad.  The last five years of my life have been a kaleidoscope of different events and opportunities, and I wouldn’t have it any other way! 


But, lots of people think that working remotely and using the world as your office is a dreamworld full of rainbows and butterflies.  WRONG! Unfortunately, remote work still has its share of challenges and frustrations. 


I love helping people build freelance careers of their own, but here are the Top 5 Things one should know before jumping in:





As a freelancer, you will never have a guaranteed job or income, so some weeks may be feast or famine depending on the amount of work you can find.  Although rare, there are days that I am underutilized as a copywriter because of gaps in different client projects. Those days makes me anxious. 


How am I going to pay my bills?  How will I find my next client? What if a client doesn’t fulfill our agreement and I am not properly compensated?


Many of these types of questions will run through your head especially when you are trying to land your first client.  And unless you have a big savings account, you may be living off of bread crumbs in the beginning of your career.  Unfortunately, being a freelancer means that you can’t expect to have regular income (unless you land a client that keeps you on retainer for future projects).  Just like taking an exotic vacation, make sure to prepare yourself well before you start.  Do your research and try to build some savings.  It will make the uncertain times you face as a freelancer much easier to deal with.  





Although the World Wide Web offers a significant amount of resources at your fingertips, this also means you will always have ample competition.  So, before quitting your day job, make sure to have your portfolio together so that you can hit the ground running.   People in need of freelance services online almost always require samples of your previous work so be prepared!  If you build an impressive portfolio before looking for gigs, you will have a better chance at getting the types of jobs and income you want.


Also, experiment with a few small freelance jobs on your free time to see what it takes to get work.  Get familiar with the different freelance job boards.  


Globe Hacker has a great list of recommended freelance marketplaces.  Create a profile, upload your portfolio, and get started!  That way, you can feel more secure and confident about leaving the cubicle world.  





Another big risk is your client not fulfilling your contract agreement. I was scammed multiple times during my first year of client work.  I remember spending weeks working on a project, only have the client refuse payment or even in one case, send me inappropriate photos after the job was done.  Just because someone hires you, it doesn’t mean that they will be professional with your project.  


To avoid scams, ask for your client to pay upfront or work through a verified third-party employer like Upwork. Don’t immediately assume someone you meet on Linkedin is trustworthy.  Do background checks and ask for a reference.  Luckily, by using a freelance marketplace, if any issues arise, you have a third party to help resolve the situation.  





There are several reasons why remote work is not suited for everyone.


You like a social work environment


As a self-proclaimed introvert, starting independent freelance work was not a significant adjustment for me. I like being alone so not being able to socialize during my workday was never a problem. But for some, this would drive them nuts. 


I tried to convince one of my closest friends to find a remote job so that we could travel and work together. Her response was, “I can’t stand working alone on a computer all day like you.” This is totally understandable. Not everyone feels comfortable working independently and organizing their own schedule.  And while there are jobs that don’t require long hours of online work, becoming a digital nomad typically means not having “in-person” co-workers.  Although, for me, this can be a good thing since I typically find that having office co-workers can be a major distraction.


Ironically, unless you lock yourself alone in a room, you will also meet many other distracting people as a digital nomad.  Every time I try to work at a cafe, hostel lobby, or other public area, at least several people try to start conversations with me while I’m in the middle of a project. In other words, figure out the best environment for you to get work done and make sure you can shut out unnecessary distractions.  And if you crave social interaction throughout the day, work in an area where you can still find interesting people to meet.



You Are High Maintenance


Being a digital nomad requires leaving your comfort zone frequently, which includes the literal comfort you get by working at a modern office or home. If you want to save money while traveling, hostels are the best option for accommodations, but some people don’t like the idea of sharing a room with complete strangers.  Also, many hostels have slow wifi and poorly setup common areas, which can be a major issue if you are trying to get work done there. So, unless you have the money to pay for more expensive lodging, you'll have to sacrifice some comfort and privacy.  Luckily, cafes and co-working spaces can be great options to make sure that you can still have a productive workspace when needed. 


For a directory of Co-Working Spaces around the world, check out:

- ShareDesk

- Desk Surfing

- Copass

- Global Coworking Map

- PickSpace

- And this Coworking Wiki page


In other words, learn to be flexible. Since you may move from one place to another, there will be a lot of adjustments. Be open-minded and prepared to sacrifice small comforts depending on where you travel.



You Don’t Have the Right Skills (Yet)


I believe that any job that can be done online has at least some components that can be done remotely.  Unfortunately, some people are too afraid to take the plunge into remote work because they feel they don’t have the skills needed to work independently.  My solution: either learn that skill you need or start small and build your knowledge base as you continue to grow. 


Are you a Lawyer? Become an online legal advisor. Or a Doctor? Write about your specialties and sell them as eBook. Or maybe a Construction Worker? Create how-to youtube videos.


All of us have skills we can use online.  We just have to figure out how to deliver that knowledge to the right audience.  Write down what you are good at, brainstorm about how others can benefit from your expertise, and figure out how to market that information to right people online. 





The thing I love the most about working remotely is being my own boss, but it doesn’t always mean that I am living a totally care-free life. Just like a typical office job, I have to dedicate a lot of time in my day to finish my work.  Working remotely doesn’t mean you work less, it just means you have more flexibility to decide how to get that work done.  


I easily get consumed by tasks that sometimes end up taking me more than 9 hours a day to complete.  This can make socializing with friends a rare occurrence.  Factoring in travel time, delays, and different time zones also make completing deadlines more complicated when I am visiting a new country.  


Once again, this means that as a digital nomad you need to be flexible and open to last minute changes.  Learn to be transparent with your clients.  That way, if issues arise (like your wifi shutting down or a flight being delayed) they can still trust you to get the job done.  If you keep an open mind and prepare yourself for different scenarios you may encounter, then unexpected changes will be easier to deal with.  



So now what?


Like many things in our adult lives, remote work has been a trial and error process for me. During the first years, I questioned if it was the right path for me because it was far more challenging in the beginning than I expected.  I would sometimes even fantasize about working in a modern office with a steady paycheck.  It definitely seems less complicated to have a company setup a standard 9 hour workday with salary growth opportunities, health insurance, and a 401K.  


But where’s the excitement in that?!   


My desire to travel whenever I want, along with my fear of living in a chaotic city, far outweighs the convenience of doing what most other people my age are doing.  And it can be very challenging at first to get started!  But if you prepare yourself in the right way and have a little faith, success will follow. 


This list is not intended to discourage anyone from pursuing the digital nomad lifestyle.  Rather, my goal is to help prepare anyone who is trying to go down the same path to have the right expectations before getting started.  As long as you have a step-by-step game plan, it’s actually pretty easy to find a remote job.  But, keep in mind that it takes a lot of work and discipline, especially when you are transitioning from office life to the remote lifestyle.


If you really believe that the digital nomad lifestyle is for you, then don’t let your fears hold you back. I’ve been doing it for nearly six years now and can’t wait to see where the future will take me :)


If you have any questions about how to get started with a freelance career of your own, leave a comment below or contact me @


Cyril Oh is a freelance copywriter based in Calabarzon, Philippines.

Follow her digital nomad journey at

If you have any questions about her experiences working remotely or have a project you think she would be a good fit for, you can also find her on Linkedin or Upwork