Digital nomad-ing is definitely a thing.

The term was first coined in 1993 by Andrew Gore and Mitch Ratcliffe. The duo wrote Random House guide books about the digital nomad lifestyle — which is essentially using telecommunications and technology to earn a living while traveling as a nomadic.

While the term is broad and technically includes everyone working and travelling, from entrepreneurs to refugees, the modern connotation often evokes a picture of a twenty-something sipping on an americano and glued to their MacBook Air (yep—guilty).

Of course, there’s a lot more to it than that. I found out the hard way as my foray into a digital nomad lifestyle was done more or less on a whim. I relied on bravado to carry me through trial and error phases and the many growing pains that followed. I’ve learned a lot on the fly in the past year.

What first struck me is that living as a Digital Nomad is more viable than ever before. In fact, the small country of Estonia (known for its e-residency and tech-hub status) is enacting the world’s first ever Digital Nomad Visa in 2019. It’s no longer just the answer for people trying to turn extend their year-long backpacking trip (as was the case for the first digital nomad I ever met)—it’s also an avenue for entrepreneurs who value time and mobility.

Thanks to technology, the number of remote job opportunities is ever-increasing. In many cases, remote, freelance, and contract work is also more suitable to companies than the traditional full-time formula. The flexible framework certainly caters to certain industries like writing, editing and proofreading, social media management, digital marketing, web design and programming, recruitment, online teaching, and graphic design.

What I’ve found is that there are so many opportunities out there, so many digital nomads/freelancers, and so many resources, that it was all quite overwhelming. Desperately jobless and directionless, I sifted through a ton of material in search of guidance.

Before listing those resources, here’s an idea of what freelancing can look like.


My work-life balance means mapping out a 7-day trek week from time to time (and it’s serious work too!)

My work-life balance means mapping out a 7-day trek week from time to time (and it’s serious work too!)

There isn’t one recipe for the digital nomad lifestyle but I found it constructive to see what worked for other people. What materialized for me may not be the precise formula that makes digital nomad-ing feasible for you, but it may point you in the right direction.

In this first year of freelancing, my primary source of work has been UpWork. Hustling on UpWork pays my rent, bills, insurance, and living costs. All of the other work I do pertains to developing my career as a screenwriter and author; I consider this work career development and in turn, it funds all of my travel and personal development (ie. new programs, online courses, etc.). I found recurring clients (like Virc Studios and Daily Hive Mapped) by cold-emailing companies and reaching out to my known network of contacts.

I split work into two categories: work I love that pays the bills + work I love. Over time, I’ve slowly shifted priority from jobs that pay the bills towards work I simply love. To get flexibility, you must also be flexible to change; my freelance work-life balance and formula are ever-changing, but the longer I’ve worked at it, the longer I’ve had some degree of control over designing my schedule.

When I was starting out, I literally googled “best freelance jobs” and “how to be a digital nomad” on the Internet. In truth, the internet is full of useful resources—these are just a few that helped me.

As I continue to manoeuvre the whole freelance thing, I will continue update this page with new and useful resources so if you’re easing into the digital nomad direction, be sure to bookmark this list!


7 Tips for Budding Freelancers

How to be a Digital Nomad by Location Indie

How to Become a ‘Digital Nomad by the New York Times

How to Become a Digital Nomad by Foundr

8 Things No One Tells You About Working Remotely


The Freelancer’s Toolkit


Best Freelance Websites to Find Remote Work

A Year Off The Beaten Career Path — Learn from my first year of trial-and-error freelancing.

Monday Morning Coffee — tried and tested: subscribe to the newsletter to receive a Monday morning roundup of available writing jobs (this is how I started my digital media copywriter contract with 100Pound Social).

The 15 Best Jobs for Digital Nomads

31 Passive Income Ideas


Female Digital Nomads

Freelancing Females


Nomad List

The Earth Awaits


Working Holiday Visas for Canadians

International Experience Canada

Visa 101 for Digital Nomads

*Refer to individual government websites for the most current travel visa information.


Safety Wing — this is emergency-situation insurance designed for for digital nomads (I use this because it covers climbing!)

World Nomads — insurance made for travelers


Stack — a Canadian online (no-branch) bank without banking fees and ATM withdrawal fees. Offers a pre-paid MasterCard you can tap anywhere and rewards for things you probably already buy!

Transferwise — manage earning money in multiple currencies without the headache or high conversion fees!

N26 — an online bank with free ATM withdrawals across Europe, an intuitive app with instant notifications, and cool see-through MasterCard debit card.

How to Manage Your Money as a Digital Nomad


Demistifying Digital Nomad Taxes

Filing Taxes as a Digital Nomad — everything you need to know

10 Tax Deductions Every Freelancer Needs to Know

Sole Proprietor vs. Independent Contractor Explained

*Note: It’s always good to read up but do seek professional financial and tax advise if necessary!


Matador Network

Explorista — Linked to the Female Digital Nomads FB group

The Wallet Moth — I met Yasmin in Chiang Mai and read her blog thoroughly as I was getting started

Nomadic Matt — He’s everywhere.

Wired Creatives — Headed by Intrepid Introvert & World Nate

Making It Anywhere — a travel couple who run online businesses and have published some digital nomad books

Here’s a longer list.

ResourcesTrixie Pacis