Getting Started as a Digital Nomad

Those who know me know that I leave my home in Canada whenever I can. But many also don’t understand how I manage to do this. I can’t tell you how often I get people asking me things like  “Where are you off to now, missy?” or, “Don’t you ever work?”

I just think that there’s so much to do and see in this world and that life is too short to stay in one place. I’m not rich, on top of that, I left my full-time job to be able to travel more. But I’m not living in the streets either. 

Travel can be a way of taking a break and having some time to yourself, but to many people like myself, travel is a lifestyle. Life goes on, work goes on, only in a different place. 

If you’re reading this and are envious of people who are always traveling, don’t be; if it’s something you really want to do, you can.

I managed to travel long-term through several different ways:

While doing all these, I would post pictures on social media that make it look like I’m having fun. I am – I make the most out of where I am living at the moment. But what you don’t see is the amount of work and less-than-ideal behind-the-scenes situations that I go through.

When people ask me which method of long-term travel I recommend, I always say that if they can spend some time as a digital nomad, they should do it. Why? Because nowadays, with remote work on the rise, it’s easier to become a digital nomad. It’s a flexible lifestyle; you have all the freedom to go where you want to go, however long you want, whether it’s one month at a time or one year at a time. When you move for a specific job, you don’t have a lot of freedom and flexibility. 

What is a digital nomad?

A digital nomad is someone who can work from anywhere in the world. They either have a full-time job that allows them to work from anywhere, whether it’s at home or from a beach halfway across the world, have their own business, or are freelancers who only need a laptop to get their work done. 

When I digital nomaded (is that even a verb? It is now!) I took freelance jobs to make a bit of money while traveling. I taught English online and would take freelance writing jobs. I never went full-time freelance, but even making $50-$100 per week helped a lot in countries like Spain, where rent cost me about $300 USD/month a glass of wine cost $1-3 USD.

Simply put, digital nomads just need a laptop, strong WiFi and quiet spaces to work from, anywhere in the world. 

How to Get Started as a Digital Nomad

How do you find work as a digital nomad?

Nowadays it’s easier to find jobs that allow you to work from anywhere. Many companies are switching to remote-only, or at least hybrid models. A friend of mine recently told me she was frustrated at how hard job-hunting is. She’s right. It’s important to remember that job hunting is still a process – it may take you a while to find the position that is perfect for you – for example, many employers will restrict their employees to certain time zones, while some will want you to still come into the office on certain days. 

When I was job-hunting years ago, pre-pandemic, I spent 10 months applying to multiple jobs per day. But I encourage you to not give up! I have compiled a list of over 500 places that hire remotely, feel free to use that as a starting point for your job hunt. Don’t forget to let me know if it helped! 

Where do digital nomads live?

That really depends on your budget and what kind of lifestyle you want to live. Here are some options:

Rent a room or apartment on Airbnb or Vrbo.

Tip: If you’re staying long-term, only book a few days on the sites, then contact the host and see if you can pay them another way if you extend. They will usually say yes, as Airbnb and Vrbo take a percentage of what you pay them.

Book a hotel or hostel.

I’ve found good deals on, and Hotwire. Agoda usually has cheaper prices for solo travelers. 

Ask around as the country you’re in might have their own rental sites. 

In Spain, I found rooms via Facebook groups, Piso Compartido and Idealista.

Use Facebook Marketplace 

Filter your search to short-term if you’re only going to be there for a few months. 

Stay in a co-living space

Co-living spaces are furnished living spaces which you would share with other travelers, expats or nomads. Co-living spaces aim to foster a community of travelers and often organize social activities and outings. Think of it like a hostel but with high-end apartments with private rooms. has an extensive worldwide directory of co-living spaces. 

Join a co-living/coworking retreat

Check out my post on the different types of coliving/coworking retreats and how to choose one.

House or pet sit

Stay in someone’s house for free in exchange for taking care of their house or pets. I have never tried this myself, but I know a few people who have used TrustedHousesitters and had good experiences. 

What are some pros and cons of the digital nomad lifestyle?

Some possible pros:

  • The flexibility to work from anywhere
  • The ability to travel more and make your own schedule
  • Less stress and more peace of mind
  • More opportunities to expand your networks and horizons
  • Increased creativity – you will be inspired by new people and environments
  • Expense cuts – think cable and electricity bills, transportation and rent

Some possible cons:

  • Loneliness – as you’ll be away from your family and friends
  • Distraction – it might be hard to stay productive if you’re in a beautiful place
  • Unpredicted situations – anything can happen. When I was in Costa Rica, the internet network went down for a whole day – in a digital nomad hub. 
  • Burnout – time zone change, distractions, unforeseen circumstances and travel hype could lead to burnout

What are some useful digital nomads can use to stay safe?

U.S. Department of State – Travel 

Check travel advisories and safety information for U.S. citizens traveling abroad.

Canadian Government Travel Advisories

Recommendations for Canadians traveling abroad. 


SafetyWing is a travel medical insurance that was created by nomads for nomads. It has actually made life easier for me several times because you can purchase a policy even if your trip has already started and it’s also much cheaper than any Canadian medical health insurance. You’re covered in 185 countries and you don’t need to let them know about your itinerary in advance. They are an affiliate partner, so if you check them out at this link they’ll know I sent you. 


Avoid getting your password lost or stolen. Dashlane is a web-based password manager that securely stores your passwords. The Premium version comes with dark web monitoring and a built-in VPN – get 6 months free trial with this link (that’s my referral link).


I heard about this app from several digital nomads, but haven’t used it myself. It helps you organize your travels and keep track of your travel itineraries and stay informed about any travel disruptions or changes.

Got questions about getting started as a digital nomad? Comment below!


You Might Also Like

Leave a Reply