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If I Had To Work From Anywhere Again, Here’s What I Would Like To Know


Picture this: the sun setting over a distant beach, your laptop glowing with the last rays of daylight (perhaps you’re in an open cowork or cafe, who knows) and the world as your office. Sounds amazing, right?


Working from anywhere can be an incredible adventure, but it also comes with its own set of challenges.


If you’re thinking about taking the plunge into location freedom, here’s what I’ve learned from my own experience to help make your journey smoother and more successful.


1. Get Your Work Sorted Before You Travel


Before you pack your bags and jet off to an exotic location, make sure you have your work situation sorted.


Knowing how you will make money online before you start your nomadic journey is crucial — whether you have a remote job or are starting your own online services business. Don’t wait or assume you can figure it out once you’re on the road because, trust me, chances are you’ll be distracted.


When I first started, I was doing a tech start-up and also helping people with their presenting skills through my online public speaking coaching business. In other words, I had a plan and something to focus on when I started nomadding.


If you’re starting your own business, make sure you do the groundwork before you head off — your market research, knowing your customer, finding your niche and even getting some early testimonials (all things I help with in the ImagineThat Academy).


The last thing you want is to be stuck in a foreign country, scrambling to make ends meet. It wasn’t always easy, but having financial stability allowed me to enjoy my travels without constant stress.


2. Pick The Right Places


Not all destinations are created equal when it comes to working remotely. You need to choose places that cater to digital nomads. Here’s what I look for:


  • WiFi Quality: Reliable internet is non-negotiable, obviously. I always check reviews and ask other digital nomads about their experiences. This is a factor that NomadList ranks places by too, so you can check there.

  • Cafes and Coworking Spaces: Having good spots to work from can make a huge difference. I look for places that are laptop-friendly and have a productive atmosphere — it’s also a great way to network and meet other professionals.

  • Digital Nomad Community: Being around other digital nomads can provide support and much needed social interaction if you’re away from home. I try to find destinations with an established digital nomad community and have made some incredible friends as a result.


3. Know That It Looks Scarier Than It Is


Deciding to actually go is often the hardest part. The build-up and the “what-ifs” can be incredibly intimidating. But here’s the thing: once you take the plunge, you’ll adapt faster than you think. The fear is mostly because this lifestyle is different and outside the norm of what most professionals are doing. But embracing the unknown led to some of the most rewarding experiences of my life. And the time is ripe — the world of work is changing at rapid speed to accommodate this.


I remember feeling anxious before my first trip, wondering if I’d made the right choice. However, once I got going, I found that I could handle the challenges and started to enjoy the freedom and new experiences that came with it. 2 years later and I have been to 7 destinations and counting. Who would have thought?


4. Make Sure To Stay Connected


Just because you’re working from a different location doesn’t mean you have to lose touch with your network. It’s essential to keep up with old connections, including colleagues, mentors, and valuable contacts. Regularly schedule video calls, participate in online communities, and don’t hesitate to reach out to your network. Staying connected will not only help you professionally but also allow you to stay grounded by connecting with familiar faces.


I made it a point to keep in touch with some of my closest mentors and colleagues, which helped me gain helpful perspectives and continue growing in my career.


5. Start Small


You don’t have to commit to a year-long globe-trotting adventure right off the bat. Start small. Pick a place for a few weeks and see how you like working away from home. This approach allows you to test the waters and adjust without making a huge commitment. If you enjoy it, you can gradually extend your stays and explore new locations.


My first stint was just a month-long stay in a nearby city with a good nomad community (Valencia, Spain). It gave me a taste of the lifestyle and helped me understand what worked for me and what didn’t.


You don’t have to “be” a digital nomad or not — you can choose how often and how long you want to go away for. Some of my clients simply want to do it for 3 months of the year over winter, others, for longer periods.


In Conclusion


Working from anywhere is an exciting and liberating experience, but preparation is key.

Secure your income, choose your destinations wisely, don’t let fear stop you, stay connected with your network, and start small.


If you find this useful, you can join the free ImagineThat community of 500+ ambitious but bored professionals who want to start an online services business and work from anywhere.


Want to work more closely with me or start an online services business that will give you location freedom? Reach out and connect with me on LinkedIn or check out the ImagineThat services.

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