Jenny on laptop on beach

Location-Independent Freelancing: The Good, the Bad, and the Ugly

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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.

Jenny Apartment

Ahhhh… paradise.

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.

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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.

Jenny - Sunset view

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?

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  1. Avatar Nicole Rossetti le Strange says:

    Oh, goodness yes – the power cuts! Last year we (my partner and I) lived in Fort Kochi (Kerala) for several months, which was wonderful; amazing food, fantastic people, wonderful way of life, friends, community, backwaters, the sea – almost everything we could want, really. However, the closer it got to monsoon season, the more frequent the power cuts became, so in addition to the scheduled daily 30-minute outages, it would just go off at random times, for random periods. We found ourselves chasing the internet all over the town, moving from one café to another. And even when it *was* working, the internet was pretty rubbish anyway, so one of us would work online while the other did offline stuff, and vice-versa because we couldn’t both be online at the same time. It was rather infuriating, and, as you say, mentally draining.

    Last year we spent five months living in Taroudannt (Morocco), which again, was a fantastic place but the 21st century hadn’t quite arrived, so while there were no power cuts, the internet was still very poor, which made work incredibly slow.

    We’re back in Chiang Mai now (which really does feel like home!), and yes, we know where we can work, where has great internet, where is comfortable, and where to avoid because the students have all ‘reserved’ the comfortable seating!

    We leave here in July (we tend to stay for six months at a time in CM), and plan to go to Eastern Europe for a few months, until it starts to get cooler, and then to Central America. Of course, we all know what they say about the best-laid plans…. 🙂

    So glad to have discovered your blog (via – as a wandering, tech-head, freelancer, this is right up my soi!

  2. Thanks for your awesome comment!

    The most frustrating part for me, is knowing how quickly I can get stuff done in a good environment and fast internet… compared to when you struggle with internet/power/mental fatigue. And when technology isn’t working I want to throw things. haha.

    Chiang Mai is awesome. I was there for about 18 months and loved it. We’re thinking of heading back to Asia, but who knows what the future holds.

  3. People who don’t know me well often look at me weird when they see how much time I’m on my laptop or when they discover that one of my top priorities when preparing to go to a new area is that I have good, reliable, fast WiFi. I’m sure for many people it just looks like we’re on an extended vacation when in reality we’re working hard. It’s just that our office and its location change frequently, and like you said, that in itself creates a whole different dimension.

    1. Exactly. It’s funny because many of the people I’ve met on shorter trips are always jealous that I can work on the road indefinitely.

      But me? I’m jealous that they can be on a 3, 6, or 12 month vacation without having to work during that time. It’s freeing to not have to worry about internet so much! I’ve done a 5 month stint where I just traveled and didn’t work. It was awesome…

  4. I can totally relate to this. I work for an online graduate school and have to make calls back to the US through Skype. I dealt with power outages in San Juan del Sur and found the one guy in town with a phone connected to a generator to make my calls. After many close calls I’ve learned to keep a backup plan – if internet goes out in my hotel/apartment, I know where the nearest internet café is located. But you’re right that sometimes you just have to suck it up in a less than desirable place with a good connection until you have internet-free time to spend in more remote areas.

    1. Skype. Sometimes it’s great and other times it’s not. I’ve often had to reschedule calls because of internet issues. I usually test it beforehand, but then if the place gets busy or people start downloading stuff it can change the quality quite drastically.

      It’s funny but the place in Managua had the fastest internet I’ve ever had on the road.

  5. Being held prisoner to decent internet is a miserable situation. As is accommodation without a decent table and chair if you’re trying to work while on the road. I don’t know how the backpackers living from one dorm to the next do it!

    1. Given that I have some serious medical problems, a proper chair and desk is godsend on the road.

      The condo we’re in right now, is great for working and I have about 4 different desks I can choose from. I’m going to be sad when it’s time to leave this house!

  6. Avatar Caz Makepeace says:

    Great post! Can totally relate. The whole decision fatigue has been really screwing with me. That’s why we’ve chosen to get a camper trailer with solar panels. I can’t handle all the research and decision making any more about where to stay. Now we’ll just stay where we want to pull up with the office ready to go- 5 min decision.
    Long term travel whilst freelancing is a whole new ball game.

    You know we love ya and your work!

    1. Decision fatigue is a real thing! Can’t imagine how you guys do it with kids as well… Enjoy the camper, that’s going to be quite nice to have.

  7. I’m so grateful for blog posts like these that give the alternative side to life on the road. It’s easy to think it’s all rainbows and roses, but there are SO many things to consider in advance. Thanks for sharing!

  8. This is the story of my life too! I took the risk of going to Nepal thinking that I’m prepared for the power outages and limited internet connectivity. Well, I under estimated it.

    End result, I lost clients boo! But I’ve got tons of priceless experiences offline and I think I will never had experienced if I’m always in front of the computer.

    But now I’m back to regular programming, back to getting more online work so I can travel more

    1. Glad to know I’m not the only one! 🙂

  9. Avatar John Wilson says:

    Yupper, you cannot figure this stuff out ahead of time.
    Who’d believe that a popular tourist town would NOT have power for hours or days at a time?
    How can you not have electricity or internet – in the middle of no where? LOL
    I stayed in Waslala for a week, and they had 1 internet connection at a local Menonite store for the whole town.
    It took me about 4 months to realize =- SLOW DOWN!
    It’s not the places you visit that are important – it’s the people you meet that make it worth the effort.
    2 to 3 months in one place was ideal – got to know the town, a few people and where I could connect to the internet that was good.
    I don’t think if you live in the States or Canada (Possibly Europe) that you can realize the challenges that are faced daily by 70% of the world population .
    Questionable electrical service, off and on wifi connections, corruption that interferes with your travels. roads that are nor passible to get where you want to go, questionable hotel services and amenities, and so much more.
    But, that’s the intriguing and challenging thing about traveling the world and making a bit of money while doing it.
    Like the saying goes – It ain’t the destination – it’s the journey that’s the fun part.
    Great that you have found a way to “settle” in with your travel and work.
    I could relate to many parts of your article and empathize with the challenges you face.

    1. I know right. I was shocked at how much the power was out in San Juan Del Sur. In one of those weeks, we only had 1.5 days of online time. The power was off all day, but worked flawlessly at night, bastards!

      Never crossed my mind to think that a popular tourist town would have power issues that badly.

      Long term, it is about slowing down. We found that vacation rentals seem to be our best bet for a minimum of one month. Currently in Puerto Vallarta for six to launch Never North. We really needed the stability and break.

      I learned how important environment and work space are to my productivity and that’s something I could have never realized before I left home. You’re right about that!

  10. Awesome post!!

    I think one of the toughest parts is realizing that when you have your own business, you can never fully take a vacation unless you formally cease work on projects. I’ve become jealous of friends who can take purely fun vacations with the mental break from work, because I’ve always gotta be checking my emails to make sure nothing urgent came up.

    The tools you mentioned for putting your resources online are topnotch–I’d add CrashPlan to the list. As a photographer, I’ve got terrabytes of files that I continually have to reference, and carrying around physical hard drives is a pain. Services like CrashPlan are great for eliminating that.

    Also, I do a lot of remote work in social media and have found that sites like Facebook make this nearly impossible with their geolocation trackers–half the time, I need to (with guilt) tell my clients I need them to unlock their Facebook accounts b/c Facebook detects I’ve traveled to a new location. A big pain I haven’t found a solution to yet.

    Thanks again for the blog, and I’m excited to try out freelancing from Thailand next week–my first trip out there!

    1. Thanks Suzi. I’ll have to check out CrashPlan. I’ve heard of it before, but haven’t really looked into it.

      I have been using Cubby and Dropbox, but I DO NOT recommend Cubby. It’s super buggy, customer support sucks (took a month to reply to my support issue and is still unresolved 7 weeks later). AND, it uploads at about 20% of the speed that Dropbox does and is often missing files when it says it’s fully synced.

      I often have to reauthenticiate because I change my location on accounts, but I’d rather deal with that pain in the ass, than be less secure.

    2. Dave Dean Dave Dean says:

      Suzi — I’m also a big fan of Crashplan, and recommend to anyone who will listen (and to be honest, anyone who won’t as well… ;-))

      Regarding the geo-location annoyance: I’d suggest using a VPN like Hotspot Shield or Witopia to let you choose a location that Facebook likes a little more than the one you’re in. You could use a proxy service instead, but given the significant extra security benefits of a VPN, you may as well go for that option.

  11. Gah, it’s so nice to hear from someone else that they don’t have it all figured out.
    I’m currently in Nicaragua for a few months in Matagalpa, and have a solid internet connection. Sometimes I find these places easily, and sometimes it is one headache after another. I haven’t had any issues with electricity yet, just water. I’m sorry that you got stuck in Managua, that place really is the pits for travelers. (I’m working on my write up of it as we speak.)
    I think that the worst for me is exactly what you said, finding these new places…over…and over…and over again. It can get exhausting.
    That and trying to explain “my job” to people. That only seems to get more complicated the more that I travel and the more that it webs out in all different directions. Friends and family back home think that life is all sunshine and rainbows with one exciting adventure right after another, but what they don’t get is that I’m really more of a dispossessed expat than a wandering backpacker 😉
    The best part for me though is getting closely acquainted with the culture, and seeing sites that aren’t in any travel guides. I currently live with a woman who survived the war and the revolution, and I love hearing her stories. I have lived with multiple families in multiple countries, and I learn so much from each and everyone of them. <3
    Tina of Full of Wanderlust

    1. That is amazing. What an incredible journey you’re on.

      I prefer slow travel too. I feel like I really know the places I’ve been and I think that’s pretty cool.

      And yes Managua sucked, we could barely leave the house. But it was the fastest connection I’ve ever had on the road with 2MB/s downloads.

  12. Avatar Anne from Viajar y Amar says:

    Phew! Somebody said it! It is hard to work while traveling. It is awesome to travel. It is awesome to have some money. But the getting to the balance is really hard. And that’s if you *don’t* get the Guatemalan gut rot or Dengue. I’ve done some really good work while holed up in Boquete, Panama (5mbps) and Medellin, Colombia (10mbps!!!!) but the Costa Rica days were super hard. I pretty much quit trying.

    I’ve come to a similar conclusion as you, so let me try to refine that mezcla here: holing up in a beautiful, wifi-strong, infrastructurally-sound area is awesome for getting work done for a few months, but then taking time to let our minds and hearts breathe in a place for a few weeks where the power goes out for 1/2 days at a time creates the much-needed break from digital life. We’re creative people. We need to stop treating ourselves like robots.

    The beauty here is that we CAN get month- and week-long leases in beautiful places. We DON’T have to stay put. We CAN go back to our favorite places to get work done and we CAN go take a break somewhere cheap and close and beautiful.

    We’re getting it figured out… slowly. 🙂 BTW we’re in Medellin, Colombia and we’re loving it for our city phase. It is a big city and it is beautiful. If you’re looking for potable tap water, lively city parks, and a metro that connects you to everything, this will scratch that itch.

  13. This is just what I needed. I am about to take a 3/4-month trip to Cuba, Mexico and Central America, and plan to work on the road. WiFi is pretty much non-existent in Cuba so I’ve written that off but I think I was quite to naive to assume it would be much better everywhere else!
    I realise it’s going to be tough – particularly when you constantly have to make careful decisions about EVERYTHING, which will be very draining – but I am determined to make it work.
    Thanks to you and commenters for all your tips!

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