Life on the road. Working from your laptop at the beach, breathtaking sunsets, and endless adventure. This is what being a digital nomad is all about, right?
Well, not really. It’s not all dreamy sunsets and fireflies. The road presents a unique set of challenges, and if you aren’t prepared, it can lead to disastrous outcomes.
As a freelancer you have clients and responsibilities, projects you committed to and took money for. It’s different to running a blog or other website for a living: while those folks often have the same challenges, they tend to have more flexibility than a freelancer with committed deadlines.
I’m no stranger to remote working. I’ve been running a successful location-independent business for 13 years now, with the last three as a digital nomad.
I thought my location-independent experience in my cushy home office was more than enough to prepare me for working life on the road. At the time I had ten years of successful freelancing under my belt, with a healthy work/life balance. Surely it couldn’t be that different?
I must have been delusional.
Decision Fatigue & Mental Energy
Working while traveling adds a complex set of problems to your workflow. Things you take for granted at home become daily choices and problems to solve.
The amount of decision-making you have to do is intense. Where am I going to eat? Sleep? Work? And where can I find a good Wi-Fi connection?
It may seem simple, but when you’re in a new place all the time, it requires way too much effort to do basic things. You can’t just go to your favorite coffee shop to work, you have to find one. Over and over again.
Where is it? How do I get there? What does it cost? Then there’s the problems that you can’t predict… like the hotel you booked online that promised Wi-Fi in the rooms, but actually only has it in one. Which is occupied.
It is what it is.
Chasing a stable internet connection and decent work area is exhausting. All the thinking you have to do about basic things consumes a ton of mental energy.
That’s mental energy that you no longer have for your freelance clients. When you’re working in less than optimal conditions, it takes you longer to do your work, especially creative work. Work that used to take me a few hours can sometimes now take days. It takes longer to find answers when your creative process is interrupted time after time.
If you aren’t prepared for it, it can have less than desirable consequences.
And Then Things Go Wrong
For example, we decided to stop in San Juan Del Sur, Nicaragua for a few months to get some serious work done. We had some client projects to finish and wanted to launch our own project (NeverNorth) as well.
There was fast Wi-Fi, great beaches for surfing nearby, and fresh seafood for super cheap (a kilo of lobster for $7!!) It felt perfect for the balance we were seeking, and we found a house with lots of light and a beautiful view.
Until we were on deadline and the power went out. For eight hours. The entire town was offline and in the dark. There was nowhere to go to get a connection, and I failed my client.
Over the following weeks we found that this was a near-daily occurrence, ranging from a few minutes to an entire day offline.
This set us behind on our client projects (and killed any hope of working on our own project), increased our expenses, and left us to figure out where to go next.
Out of options, we ended up spending a month locked in a tiny windowless room in Managua out of desperation for a solid connection to meet deadline. Not only was it difficult to work in a dark room, Managua isn’t a great city to hang around in.
I was unprepared for the shift and I created a living nightmare for myself. The lifestyle that was supposed to give me freedom gave me handcuffs instead.
When you’re working on the road, you can’t just sleep in an 8-bed dorm room and expect to be able to get high-level work done. You need a comfortable place to work, with solid Wi-Fi and a good night’s rest.
Cafes, while awesome, are difficult to be productive in if you need silence for a Skype call or to concentrate.
While everyone’s needs are different, you need to consistently find a place that suits your requirements. If you can’t, you’ll lose valuable productive time, which then means less time for adventure.
There are just some things that get old about the lifestyle, and I think that’s why places like Chiang Mai are so popular. Not only are they cheap, with a strong community to connect with, but a few months there provides a bit of stability. You know where to get a fast connection, a good coffee, a quiet place to work.
It’s not home, but it feels like it.
You can let go of the mental energy it takes from making decisions all the time, and focus on the important stuff, including friends. Being able to form connections in real life rather than just online is healthy for the soul. Nothing beats a good hug from someone who gets it.
What I Would Do Differently
I’ve learned a lot on the last three years of my journey, and if I had to do it all over again, would do a few things differently.
First, before I left, I would have prepared my business systems for life on the road. The tools and systems I used back home in my office to freelance are not systems that worked on the road.
For example, I had a library of 300 design books I could reference. I would find things that inspired me for a project and paste them to a bulletin board, or use my box of art supplies for comping.
Since I’m a visual person, my project management system was made up of tickets I moved around on my wall. It was easy for me to see and understand. My backup system was made up of several large hard drives, and I was used to working on a 23” monitor.
None of this transferred over to my new working environment. I couldn’t carry 300 design books or boxes of hard drives and art supplies around the world with me. My project management system no longer worked without an office, and a few programs didn’t work offline. When the connection was crap, I wasn’t working.
Not to mention going from designing on two monitors to a 15-inch laptop screen. My time estimates became wildly inaccurate, which made scheduling problematic.
It was a systems failure. I wish I would have recognized months before I left that I needed to have new, entirely digital creative processes and business systems.
I’d spent years perfecting my creative process, so it was a challenge to find what worked for me under the pressure of deadlines and traveling. Had I figured it out beforehand, I believe the transition would have been much smoother. Thankfully there are several great companies out there today like Asana, Evernote, Pocket, and Dropbox that make life so much easier.
The second thing I would do is work in cycles. I got tired of compromising on things because I needed a connection. I found great places, but they had power or internet problems. The need for reliable infrastructure took places I wanted to go off my list.
Instead, I would choose to stay somewhere that had a comfortable place to work, stable internet connection, and low cost of living for 3-6 months. Ideally this would be in a “hotspot” city so I could form friendships as well.
It would allow me to do my work, save up money, and not have to worry about finding an internet connection all the time. Most importantly it would free up my mental space to do better creative work faster.
Afterwards, I’d take a month to travel and go places where I don’t have to worry so much about internet. I’d schedule my projects more effectively, and take extended time off where I just have to do some maintenance work.
It’s a work in progress, as it should be. Don’t let us fool you with our sunset pictures into thinking we have it all figured out, because we don’t. We’re all just adapting and learning as we go.
Do you freelance from the road? What challenges have you faced in doing so?
This post is part of Digital Nomad Month on Too Many Adapters.