Before I ever boarded that one-way flight, I had one burning question: how the hell was I going to afford this lifestyle? Sure, I had some savings—but savings don’t stretch far in cities with $6 lattes, co-working memberships, and the occasional splurge on street tacos (non-negotiable). Finding remote work as a digital nomad can be challenging.
So, I got scrappy and tested multiple income streams. I tried freelance writing, virtual assistant gigs, affiliate links, and even selling digital products. Some completely flopped. Some paid for groceries. And a few turned into long-term income sources that helped me build a sustainable nomadic lifestyle.
If you’re wondering where to start, here’s how I actually found real, remote work as a digital nomad.
Best Platforms to Land Your First Remote Gig
When I first dipped into freelancing, job boards were my lifeline. Here are the platforms that worked for me—and countless other nomads I’ve met on the road:
- 🧑💻 Upwork→ Perfect for beginners offering services like writing, design, coding, or customer support.
- 💼 Toptal→ For seasoned pros in software dev, finance, and design. The vetting is tough, but the projects pay well.
- 🧰 Freelancer→ Solid option if you’re just starting out and need to build experience through smaller, short-term gigs.
- 🌐 FlexJobs→ Curated listings of remote jobs with zero spam (yes, you’ll pay a small subscription fee, but it’s worth it).
- 🌍 Remote OK→ A clean job board featuring categories like marketing, development, design, and customer support.
- 💬 Remote Rebellion→ A community and job board focused specifically on helping people break into the remote work world.
- 🧳 Nomad List→ Famous for destination data, but also has a growing job board and active community of digital nomads.
👉 Related reading: If you’re curious about long-term career options, check out my post on Top 20 Jobs Digital Nomads Can Thrive In
Networking: The Hidden Job Board
Here’s the thing: not every opportunity comes from a website. Some of my best gigs came from simply being active in digital nomad communities.
- Facebook groups like Digital Nomad Jobs – Remote Work & Travel are underrated treasure troves.
- LinkedIn communities focused on remote work can connect you with recruiters and founders directly.
Pro tip: don’t just lurk. Join early, contribute often, and be genuinely helpful. People notice when you add value—and that’s how trust (and job offers) get built.
If you want to dig deeper into this, read my guide on Networking Opportunities for Digital Nomads—because honestly, your next paycheck might be one conversation away.
From Side Hustles to Sustainable Work
In the beginning, I said yes to almost anything. Some gigs barely paid for a week of coffee, while others helped me land bigger clients later. That’s the key: use small wins as stepping stones.
Over time, my approach shifted from “take whatever I can get” to “build a freedom-aligned business.” I share more about that transition in my article on Career Development as a Digital Nomad.
The goal isn’t just to survive on the road—it’s to thrive.
Atypical Last Thoughts
Finding remote work as a digital nomad isn’t always glamorous. You’ll pitch gigs that go nowhere, take jobs that pay less than they should, and wonder if it’s worth it. But stick with it. Each attempt builds experience, connections, and confidence.
Start with the platforms. Plug into communities. And remember—every conversation, every small project, every “failed” attempt is part of the process.
Because one day, you’ll look back and realize your first paycheck was just the beginning of a much bigger adventure.
Meet Carter
I’m Carter, an American traveler living in Portugal and the creator of Atypical Vagabond. After selling my technology business, I traded the conventional path for slow travel, life abroad, and a slightly unreasonable number of long walks across Europe. I share honest Portugal guides, Camino stories, digital nomad advice, and practical lessons to help you explore the world with greater confidence and purpose.
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