New year, new ideas, new plans. Could this be the year when you finally take to the road and start out as a digital nomad? It could be a long-held dream to ditch the office and the 9 to 5 work schedule and do it your way. No time like the present to seize the day! If you have never freelanced before, it can be a petrifying thought, let alone travelling while doing it. Believe me, I know!

When I started out as a freelance digital nomad 7 years ago, it was scary. The idea of going away alone with no one for company? No one to bounce ideas off on a work issue, or to chat to about my day over dinner? Now, the new version of me gets very excited by the prospect of an upcoming trip. It’s my time to do what I want to do, in my own time and on my own terms. But more importantly, it’s my chance to see the world and meet some wonderful people, all while running my own business. So if you’ve ever wanted to go digital nomad but was never sure how to get started, here’s all you need to know!

Why work and travel?

We all enjoy travelling for different reasons. As a short break, a longer holiday or an even longer (perhaps even open-ended) trip. Nowadays, having a job or running a business is no reason to stay in one place. Provided, of course, your job allows you to do that. Let’s assume for now, that being in one physical location for your work is not a constraint.

If you need some help or inspiration on how to start or build your freelance business, head over to A Leap of Faith: So You Want to Go Freelance blog. It covers everything you need to help you find your niche or scale up your business so that it is giving you a decent income.

If you are new to travelling, it can also take some time to feel comfortable being on the road, especially if you are alone. But that’s not a reason to miss out. So whether you are going solo or not, here are a few ideas on how to start digital nomading while taking your business with you.

Working on a park bench outside the library in Hot Springs, North Carolina

Step 1: Start out at your local cafe or library

If you are not accustomed to working away from your regular, familiar environment, start with a half day at your local library or cafe. The key to this is to get used to setting up your workstation in a new place and test out or get the WiFi working. You want to check how you work in an unfamiliar environment and figure out whether there are any new or different tools that will help you focus on work. For example, if there is background noise, do you need some noise-cancelling headphones or your own music? Are there parts of your work that you simply can’t do away from your own hotel room or private space?

Take as many of these working trips as you need when starting out on your digital nomad adventure. There’s no hard-and-fast rule of when you will feel comfortable working like this. We’re all different and the point of these shorter trips is to help you feel relaxed and confident that you can navigate an unfamiliar environment and still be productive. Once you are comfortable doing this and working well, guess what?

You’re a digital nomad!

Step 2: Make it a day trip

Once you’re happy you can carry what you need, set up and get some work done, why not add in a bit of exploring to your day? Being a digital nomad is about being able to work remotely so you can explore.

If you live in or near a town, pick a part of it that you’ve never visited or one that you haven’t been to for a while. If you’re in the countryside, heading to a nearby city could be your day trip. Make sure you pick one that you haven’t visited for a while, not where you go for your regular shopping.

Plan you’re work as well as what you can do while you’re there once you finish. It could be visiting a museum or exhibition that interests you. Or it could be wandering around the cobblestone streets of an old part of town. You want to have a destination and a plan of what to do to keep yourself occupied, so you’re not fretting about being alone or working all day.

Don’t forget to factor in lunch! You can either scout out a place out when you get there, or plan ahead and have picked out somewhere in advance. You could eat where you’re working (always a good idea to support local businesses where you can), or you could grab a sandwich and eat in a local park or by the seaside.

Proofreading on a roof terrace in Hydra, Greece

Step 3: Book a weekend away

Ready to go further or be away for longer? Book yourself a night away and take a couple of days to work and explore!

Plan out what you need to accomplish work-wise and make sure to set aside enough time for it. For your downtime, you can do the same as you would on a day trip: plan a few activities or mix it up and include joining a tour. It could be absolutely anything. A backstage tour of a theatre, a bike or walking tour of the city, a ghost tour!

Joining any kind of group also gives you an opportunity to interact with others. If you’re shy or an introvert, it’s an easy way to meet people without the pressure of finding something to talk about. If you’re an extrovert, it’s your time to chat to someone if the only people you’ve spoken to all day are the hotel concierge and coffee barista.

You may also be surprised at who you meet! Here are some of my experiences meeting people when travelling solo.

Step 4: Travel to a different country or state

If you’re feeling comfortable with a weekend away, it’s time to move on to a longer trip. Maybe even head over the border to another country or state.

The same ideas apply. Have a plan of things that you want to see or do, even a loose one, as well as know what work you need to get done. This way you’re not worried about meeting a deadline or have time to dwell and worry about being alone. I love to explore by wandering around a city or town and mixing it up with something cultural. That way I’ve got something to keep me busy while still giving me time to wander around and sightsee.

With a little more time and less pressure to do things, you can linger over lunch or a coffee (or a drink) and do some people watching. This is a great way to experience different lifestyles and cultures. A leisurely coffee at a cafe watching people walk their dogs or a lunchtime riverside bite or work location and the world starts to slow down. You forget your worries about being solo and start to lose yourself in the moment. Have a book or journal handy in case you start to feel self-conscious, but I promise you, no one cares that you’re alone.

Doing some laptop-based work from a hotel room in Las Vegas, Nevada

Step 5: Head to another continent

IIf you’ve got this far, you don’t need any more encouragement from me!

But if this is your first time far from home, or in a part of the world that is so completely different to what you’re used to, stick to the same principles. Plan your work needs and a few activities, book a couple of things in advance that you want to do, and fit in the rest of your time around them.

By now you are probably more comfortable interacting with other digital nomads and travellers you meet along the way. You’re also less likely to be worried about being alone and starting to enjoy the experience more. You have hopefully even billed a client for a finished job and got paid. If you’re on the move and find yourself stuck for suitable work spots, Workplaces for Digital Nomads may give you some ideas.

Remember: any first time will be unsettling, and that’s normal. But you’ve got this. You’ve got a system in place that works, and you’ve got things to see and do planned and ready.

Safety first

The Solo and Safe resources pages give you some tips for safe travel practices. And while Dos and Don’ts for Travellers is a little more geared to overseas travel, the principles still apply.

Whatever stage you’re at on your digital nomad journey, staying safe is your top priority. The 7 Ways to Stay Safe While on the Road can help. These apply whether you’re in the next town over or on the other side of the world.

And of course I’m always here if you have any questions or need help to get going. Drop me a line or post a comment below – I’d love to help!

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