Working from a hammock in Bali or a cute cafe in Barcelona is a dream held by many. Now that the idea of working remotely has gone mainstream, it’s increasingly the reality for many of those who can earn an income online.

(Not there yet? Then read about these nomad jobs that let you travel.)

Of course, who wouldn’t want to take their work on the road while traveling to exotic locations?

However, as with any lifestyle, there are pros and cons.

I’ve worked on the road for several years and faced a few struggles first-hand. Luckily, if you’re thinking of becoming a digital nomad, there are a few ways to make it much easier on yourself. 

The challenge with going nomadic

When you’ve found a job you can do online, it’s time to get out there and travel the world. 

While this is the start of something very exciting, I believe the initial phase is where many new digital nomads struggle. 

Of course, it’s thrilling to be hopping from place to place – surfing in Costa Rica one week, wandering through the cobbled streets of Lisbon the next. Having this level of freedom is mind-blowing.

But something that not everyone expects is that traveling is… well, a bit of a job in itself. From travel logistics to meeting people in each destination, you have a lot of work to do on top of your actual day job.

Figuring out your accommodation, transport, where to work from, and all the rest takes a fair bit of time and mental energy. Meanwhile, you’re still having to adjust to working from the road, which is quite different from working from home. 

It’s this double whammy of change — changing to working remotely as well as changing to a life of travel — that I believe can be a stumbling block.

Being prepared for these changes can help ensure you’ll be a more successful digital nomad.

My nomad bootstrap experience

When I started traveling while working on my laptop back in 2013, the term ‘digital nomad’ had not yet emerged.

My experiences may also have been atypical as far as most digital nomads go; I was working as a travel blogger while backpacking, which is a bit different from working for clients or taking your regular job on the road.

Still, it’s an experience that taught me a few things. 

My most immediate challenge? My business was not yet up and running before I started traveling. I had launched my blog literally the day before I flew off to Mexico on a trip without an end date… which was definitely less than optimal.

Today, I have a successful blog that gives me a reliable semi-passive income. But at the time, my blog had barely ten posts and had close to zero of an audience. I was not yet making any money, I hadn’t set up any effective work flows, and I was still neck-deep into learning about every aspect of blogging — from photography to SEO. 

So there I was in Mexico, excited to see Mayan temples and drinking tequila on the beach. At the same time, I was flailing around as a newbie blogger, knee-deep into startup mode, no clue about how to create good content, and insecure about my prospects for doing this long-term.

I was still just cracking this huge nut of what it is to be a blogger. And then… I had all my travel logistics to deal with on top of it too. 

Where do I stay? Where do I eat? How do I meet people? With every place you visit, you have to figure out a whole new mini-life. It’s… a lot.

Looking back on those first few months, I know that my travels suffered because I wasn’t yet comfortable in my work, which may have made it harder to enjoy my newfound freedom. 

However, my work also suffered because I was often squeezing it into my travels, trying to maximize my available time. Some of my absolute worst posts (since long deleted) were written while tapping away desperately on my laptop keyboard at a busy bus station somewhere in the Yucatan. 

My early days as a blogger remind me a bit of the stories I hear of some digital nomads who are starting out and were also perhaps a bit overwhelmed.

Going from a regular job or freelance career to a nomad life is a bit of an adjustment. It can be hard to stay focused when you’re routinely in a stimulating new environment. On top of that, the logistics of traveling long-term are also quite different from a brief holiday.

How to hit the ground running

Luckily, I think there are some good ways to give yourself a leg up. Actually, I’m not really sure how one would give themselves a leg up… but let’s just pretend this metaphor makes sense!

A situation that you ideally want to avoid is having to figure out both the travel and work stuff from scratch simultaneously. 

If you already have a nomad job or a freelance business that’s up and running, great! If not, you can start developing it while you’re at home. I strongly believe in the idea of ‘build it before you need it’. It’s better to already have a half-functioning online business or a couple of freelance clients in place than to start traveling with a blank slate.

Thinking back to when I first went location-independent, this is what I’d wished I had done. It would have helped me if I launched my travel blog at least a good six months before I started traveling. This would have given me ample time to learn all about WordPress or SEO, create a workflow for my photography, and practice my writing style by creating an initial collection of posts. By the time I’d go nomadic, I would have already been more focused and confident. 

The other way to make the transition to the nomad life a bit smoother is to make the travel part easier.

At first, it can be difficult meeting people while you travel. You often have to seek out different meetups, use social media, or find your bearings in a new place in some other ways.

A great way to practice this is through a backpacking trip or already having other travel experiences.

You could also kick off your digital nomad life by staying in a co-living house. This is a form of accommodation for digital nomads where everyone has their own room, but shares the facilities and working spaces. 

U-Co Juarez coliving in Mexico City

The huge advantage to this is that it takes care of 90% of the ‘travel’ part of nomading. You don’t have to find suitable accommodation on your own as the co-living house is already made for remote workers. You also don’t have to expend nearly as much energy on meeting people as this is practically guaranteed through others sharing the co-living space. Shared travel activities make it easy to plan your free time.

Co-livings and nomad hostels basically put your wheels on the tarmac right away. I mean, just imagine your legs are wheels and the airstrip is your life as a digital nomad; joining a co-living is like having a super smooth landing. So to speak.

Okay, maybe I shouldn’t be doing metaphors. 

Anyway, I wish co-livings had existed already when I was starting out! It’s a great way to meet like-minded people and get most of the benefits of nomading with much less of the (initial) downsides. 

You typically won’t find co-livings on hotel booking sites, so I recommend browsing Anyplace.com or Coliving.com to find the best co-livings in your destination.

Another version of the same idea is to go on a nomad retreat. These are trips with a specific beginning and end date where everyone shares the same accommodation. In Portugal, where I’m based, there are companies such as Nomad Escape and Borderless Retreat who organize group stays that combine working with travel, networking, and fun activities.

Taking the plunge

Ultimately, the best way to become a digital nomad is just to get started! You don’t need expensive courses or follow special gurus to learn how to become a digital nomad. In the end, ‘working while traveling’ is really all it is. 

It can take some time to find your groove, so don’t feel pressured to travel as fast as you possibly can. While the FOMO and desire to see the world may be strong, it’s worth staying in each new place for at least a month at a time. That way, you’ll truly get to ‘live like a local’ and the travel logistics will be less demanding. Most digital nomads don’t actually move around that much; many stay in one country for at least 2-3 months.

Anecdotally, I would say it also takes at least a month or two to adjust to the nomad life, so it’s nice to take it easy.

Set yourself up for success by not having to stress too much about either your income or your traveling. Once you get to that point, the nomad lifestyle starts to become truly a win-win.


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