7 Pros & Cons of My Freelance Digital Nomad Life

Danielle Thompson

Founder @ Freelance Travel Network, Freelancer and World Traveller


7 Pros & Cons of My Freelance Digital Nomad Life

I didn’t always dream of the freelance digital nomad life I’m living now. I grew up dreaming of creating my own business!

In every daydream, I appeared to be working in a stylish office, collaborating on creative projects with my colleagues, and heading to my swanky imaginary mansion at 5 o’clock sharp.

It was only after I landed my first serious freelance gig that I realized my career dream was kind of…basic. As I found more freelance jobs, I met some traveling freelancers (AKA digital nomads) who seemed so happy and free – all without the stability of an office job.

I was scared of losing that security, so I kept working in Montreal…until I finally mustered up the courage to take a trip to Costa Rica, freelance work in tow. ????✈️

My two-week trip stretched into a month. My dream career stopped looking like a traditional office job and started to look more like this:

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A sunset from the first work-travel trip I ever took.

I still wasn’t 100% sure on how to make my dream career happen, but I wasn’t scared anymore. Although I experienced some hiccups, giving the freelance digital nomad lifestyle a shot was the first step in realizing I could actually do it.

I met amazing freelance digital nomads from the Wifi Tribe who were figuring it all out, just like I was. They weren’t just working for money, but working for fulfillment and purpose. That kept them driven and unafraid to try new things, as long as they kept their freedom!

I was inspired. As soon as I came back to Canada, I sold everything I had. Three months later, I was back in Costa Rica, officially working as a digital nomad.Me with some of my first freelance digital nomad friends in Panama.a

Is the digital nomad lifestyle right for you as a freelancer?

That’s the oversimplified version of my story. It doesn’t include any of the ups, downs, surprises, adventures, or nightmares that I experienced while getting used to the freelance digital nomad lifestyle. It definitely doesn’t include the countless hours I spent Googling the problems that came with traveling while working.

If you’re trying to figure out if the digital nomad lifestyle will work for your freelance career, you’re going to have to read past the good-things-only type of stories. Seek out detailed experiences and be honest with yourself about whether you can handle the bad that comes with the good.

If you’re still not sure, why not check out my crash course on taking your freelance work the digital nomad route?

Digital Nomad vs. Freelancer

Before we jump into the high points and downfalls of digital nomadism, let’s start with the basics: what is the difference between a digital nomad and a freelancer? ????

A freelancer is someone who works independently, selling services to different organizations instead of being a full-time employee at one organization. Freelancers can be location-based, working with clients who are physically close, although some freelancers work remotely.

A digital nomad is a freelancer who travels while working. They work 100% remotely using coffee shops, libraries, and coworking spaces as temporary offices. Freelancing as a digital nomad means changing locations often, much like nomadic communities. Digital nomads need little more than their laptops and a Wi-Fi connection to do business.

freelance digital nomad
Digital nomads are always searching for the next horizon.
Photographer: Sho Hatakeyama | Source: Unsplash

Digital nomads frequently travel to cities where the cost of living is low and the quality of life is high. Through the freedom their freelance work provides, digital nomads frequently travel to some of the most beautiful cities in the world. ????

With the rise of the internet, more and more skilled workers began realizing they could take their work on the road. As the trend of freelancer-turned-digital nomad grew in popularity, travel guides for digital nomads helped empower even more freelancers to start traveling.

How I went from freelancer to freelance travel nomad

Costa Rica was my first destination as a freelance digital nomad. I left Montreal with just a couple thousand dollars in savings and my laptop in tow. I hadn’t even heard the term “digital nomad” before – I was just a backpacking freelancer in my eyes. I didn’t know that a different way to freelance existed; I was just dipping my toe in experimental waters!

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I was still figuring out a lot regarding my business, but the beach was a higher priority at the time!

After touching down in Tamarindo, Costa Rica, the first thing I looked for was a Wi-Fi connection. When I found a cute café to work from, I introduced myself to the other people busily tapping away at their laptops. They introduced themselves as “digital nomads,” and that’s the first time I heard the phrase that would change my life.

However, it didn’t change my life right away. Although I had already been freelancing for 3 years, becoming a digital nomad presented totally new challenges.

My mind was in vacation mode. I spent nearly all of the money I made that summer (even though I was staying in hostels). The balance between work and play became nearly impossible to manage – until I learned the fundamentals of freelancing abroad.

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#wifitribe #digitalnomads

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This is the first time I ever used #digitalnomads!

Once I was able to adapt my already-functioning freelance career to the demands of the digital nomad lifestyle, work became easier to manage, aspect-by-aspect. However, just because I’m finally on top of my game doesn’t mean I never feel the pressure!

During the difficulties of the freelance digital nomad life, I reach out to the ever-growing digital nomad community for advice and support. That’s why I’m eager to share the pros and cons of becoming a digital nomad – to give back to the freelance community that had helped me so much. ➡️

The Pros of Becoming a Digital Nomad

Just like the best things in life are free, the best things about working as a freelance digital nomad are free, too. Well, okay – one of the benefits of becoming a digital nomad just might have to do with earning more money…but it’s a side-note when you consider all the other amazing benefits of the digital nomad lifestyle. ????️

Honestly, it’s always been more about freedom than money to me. You could be earning decent money in a “secure” job but never have the freedom to explore your heart’s true desires, like travel, adventure, or self-discovery.

Even though I was scared to totally commit to the freelance digital nomad lifestyle, doing it has let me live a life I couldn’t even dream up, amongst plenty of other benefits!

Walking my own career path has had ups and downs but I wouldn’t change it for the world.

Travel, travel, travel

Before I took my freelance game down the digital nomad road, I worked from home. would sit at my computer all day trying to make something happen: find an awesome client, land a fun project, or discover the key to elevating my design business.

I’d chat with my friends about the dreams we had for our lives. Mine was always to travel! During a particularly good week when business was booming, I realized I’d already had everything I needed to make my world-traveling dream into a reality. I booked my ticket the same week.

Traveling as a digital nomad has broadened my horizons – showing me new countries, cultures, people, and ideas that give me new perspectives not only on business, but on life!

Looking at the world from new perspectives helps give us new ways to look at ourselves and our business, too. Surrounding ourselves with diverse and exciting experiences isn’t just fun, it’s good for the soul. ????️

Make your own schedule

Getting to decide our working hours is the most alluring part of going freelance for most of us digital nomads. The traditional 40-hour work week doesn’t suit most of us and has been proven to make us fat, depressed and possibly diabetic. Yikes!

Instead of conforming to really outdated work hours, freelance workers and digital nomads enjoy near total freedom when it comes to when and where they work.

It takes some testing to see when you engage best with your work. Once you can predict your productivity, you’re freed from working the same one-size-fits-all work schedule as the rest of the traditional workforce!

freelance digital nomad
Photographer: Kaleidico | Source: Unsplash

However, as freeing as it is to ditch the alarm clock, it’s still important to be organized when it comes to your working hours, regardless of when they are. Without some planning and discipline, your work will suffer and so will client relationships.

I love working on my own time, but it wasn’t always easy. It’s important to remember that everyone is different and so are their work styles and schedules! Experiment with different times and see what works best for you (then, stick to it).

Work with who you want to (and not with who you don’t)

Ever have an annoying customer that demands too much? How about a colleague that asks you a question every five minutes? Or a boss that’s such a Know-It-All, they should probably just do the work themselves? ????

freelance digital nomad
That face you make when your client says, “You’re going to need to make these changes free of charge.”

It’s safe to say that we’ve all encountered less-than-pleasant people in our working lives. Interacting with pushy, entitled, or just downright obnoxious people creates heaps of unnecessary stress and leads to overall job dissatisfaction. It also leads to lots of wasted time and lost or late wages (although there are a few tricks to getting clients to pay up).

Choosing to work freelance as a digital nomad gives us the power to choose who we will and won’t work with.

It seems like a small victory, but it feels huge when you look forward to speaking to every colleague and client you have. When we work with troublesome clients, our instinct is usually to ignore their calls and emails to avoid confrontation. That’s a huge no-no if you want to keep a decent client relationship.

Once I realized how bad my less-than-pleasant clients were making me feel, I decided to never work with anyone that I didn’t think was friendly. That small rule alone has helped me feel comfortable and eager to work on every project on my plate, doubling my motivation!

Exponential growth

When you’re working in a traditional job position, you wait to be promoted by your boss. You show up early, finish your work on time, and try to do everything perfectly so your boss deems you worthy of a raise.

However, if the company has a bad year or your boss doesn’t notice your hard work…better luck next year. ????

Digital nomads aren’t usually “wait-and-see” type people. Being a digital nomad means taking your freelance work on the road, finding what you want in life, and going to get it. Needless to say, our “promotions” work the same way.

freelance digital nomad
Photographer: bruce mars | Source: Unsplash

When you’re working as a freelance travel nomad, your career is in your own two hands. As your own biggest investor, you choose how much time and money to put into the development of your skills. Since you’re in control of your time, you decide how quickly (or slowly) you’re going to progress to the next skill level, skill set, or income bracket.

By building projects and taking courses that develop your skills, you’re enhancing your portfolio – which will stand out against the competition and justify your higher prices.

After all, you’re an expert, so grow like one! ????

The Cons of Working as a Remote Freelancer

I couldn’t imagine working any other way, but that doesn’t mean every day is perfect. Like anything worth having, a career as a remote freelancer comes with problems to solve and challenges to overcome.

However, we rarely highlight the low points of being a freelance digital nomad on our social media platforms! We can be guilty of making life seem like a worldwide cake walk, even though the real thing is far from it.

Still, it’s important to be upfront about our struggles so that as a community, we can help and boost each other up along the way.

remote freelancer
Photographer: Dane Deaner | Source: Unsplash

Without worrying about painting the perfect picture, let’s get into some of the toughest parts of juggling freelance work with the digital nomad lifestyle.

Bad travel-related surprises

The good thing about travel: anything can happen! ✨
The bad thing about travel: anything can happen. ????

Digital nomads require a reliable laptop and a steady Wi-Fi connection to get their freelance work done. Traveling to remote locations, however, can occasionally cause interruptions in our work.

During my very first trip as a digital nomad, the Wi-Fi connection at the café I was working from cut out in the middle of a Skype meeting with a client. I closed my laptop, grabbed my bag, and ran straight out the door – running across town in the hot Costa Rican sun to get back to the Wi-Fi of my hostel. I resumed the meeting 15 minutes later and even though my client laughed about it, I was in total panic mode that whole time!

remote freelance digital nomad
Travel issues can arise as quickly as a flash flood.

Traveling is unpredictable by nature, which is why we love it so much! You never know what you’ll see or experience next.

However, encountering surprises while we travel can be detrimental to the daily flow of business.

There are plenty of ways to manage the possibilities of a bad surprise, though. Communicating with your clients about travel plans, keeping an internet hot spot as a backup, and buying travel insurance are all ways to make sure you’re still on top during any kind of crisis.

Feeling isolated

Since we’re always on-the-go, the feeling that we’re all alone comes easily. This is one of the biggest challenges for every freelance worker, not just digital nomads! However, the feeling of loneliness intensifies when we’re on our own in a foreign country, unable to speak the language or understand the culture right away.

A lot of freelance workers think facing loneliness will be the hardest challenge of the digital nomad lifestyle. However, as the global community of digital nomads continues to grow, isolation becomes less and less common.

I get to meet up with my digital nomad friends all over the world!

The truth is that the digital nomad community is huge, well-connected, and honestly, pretty easy to find!

Walk into any hipster café or coworking space and you’ll find a slew of people working behind their laptops, just a coffee break away from becoming your new friend and colleague. I’ve found some of the coolest opportunities and best friends by connecting with my fellow freelance digital nomads in person and through online groups (like the Freelance Travel Network)!

As long as you’re willing to reach out to the community around you, it’ll always be there for you when you need it.????

Schedule and wage unpredictability

The daily life of a digital nomad is always changing, just like their scenery. With everything in constant motion, it can be hard to keep anything consistent, whether it be hitting the gym or how often you call home. ☎️

Many freelance digital nomads come to appreciate the unpredictability of travel, but when it comes to our salaries and schedules, unpredictability is waaaay less desirable.

freelance digital nomad
Too bad business planning isn’t as easy as travel planning!
Photographer: Simon Migaj | Source: Unsplash

Wage and schedule instability only happen when we aren’t staying on top of our business intake and output. While we don’t need to send out a proposal every day just to stay consistent, it’s still important to monitor our workload and set reminders for upcoming windows of availability.

The easiest way to stay on top of any aspect of freelance work in the midst of a busy digital nomad lifestyle is to create a system.

I love creating systems because with every system I create, I streamline an essential process of my freelance business. The system breaks down the process into its simplest parts, making it straightforward and easy to repeat.

Let’s take my monthly salary, for example. I have a systematic approach to looking for new clients and projects because I’ve taken the time to nail down who my perfect client is and what my favorite projects are. As soon as I start reaching out to potential clients, their names are added to my to-do list for follow ups. When I finally land the project, I know exactly how long to quote the deliverables – all because I invested time in a system that keeps my work consistent and easy to manage.

freelance travel nomad
The life of a freelance travel nomad is a balancing act, but it gets easier with practice.

The freelance life of a digital nomad is a balancing act; we juggle work and play to the extremes. At times, it can seem an impossible balance. With the right amount of patience, practice, and a community of resourceful freelancers at your side, it gets easier to figure out the hard parts so that we can enjoy the awesome parts.

So, should you become a freelance digital nomad?

Due to misconceptions about exactly what the freelance digital nomad lifestyle is like, some people find out that this career path isn’t right for them. While I’d never discourage anyone from pursuing the freelance path, there are simply some ideas that don’t mix with working on the road.

You’ll have a rocky road to freelance digital nomad freedom if:

  • You’re going to start freelancing the same day as your first flight.
  • You don’t want to work while you’re traveling.
  • “Traveling light” is not something you can do.
  • You aren’t motivated to seek out new opportunities.
  • You don’t like leaving your comfort zone.
freelance digital nomad
Photographer: Justin Luebke | Source: Unsplash

If none of those characteristics sound like you, great news! I truly believe that with the right training and focus on the core aspects of freelancing, the rest of the freelance digital nomad lifestyle can be figured out as you go.

It was hard work, but I learned how to make it all work for me. In addition to giving myself the career stability I dreamt about as a girl, I’ve met so many amazing people that make me feel connected to something BIGGER!

So, are you ready to make the jump to freelance digital nomad freedom and paint the career picture of your dreams? Or are you already out navigating the world? Share your questions, doubts, stories, and thoughts below!

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1 thought on “7 Pros & Cons of My Freelance Digital Nomad Life”

  1. Really love this article, has me thinking if the digital nomad lifestyle is right for me. I really want to check out Costa Rica actually – been reading your travel guides! Thank you ????

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