Guest Post By Jennifer Scott: No Address, No Problem: Building a Career and a Life as a Digital Nomad

Reading Time: 4 minutes

It’s one thing to dream of sipping coffee in a Lisbon café while knocking out a pitch deck or taking a Zoom call from a hammock in Bali. It’s another thing entirely to turn that dream into a career with momentum, income, and enough Wi-Fi to actually show up. The digital nomad life is often painted in soft pastels and panoramic sunsets, but the real work behind it is usually gritty, chaotic, and deeply rewarding. If you’re serious about swapping cubicle walls for border crossings, here’s how to make that fantasy real—and sustainable.

Picking Skills That Travel Better Than You Do
 
Before you book a flight, you need a skillset that’s borderless. Writing, web development, design, coding, consulting, teaching languages—these aren’t just digital; they’re global. If your work can be done from a laptop, it can likely be done from anywhere, but you’ve got to sharpen it so it stands out in a crowd of equally free-floating freelancers. Specializing helps: UX copywriting, Shopify dev, or even remote tax prep for fellow nomads carves a lane where you’re not just another “digital marketer.”

Crafting a Cover Letter That Lands You Somewhere New

When you’re chasing down that dream remote role, your cover letter is more than just a formality—it’s your first real conversation with a company. You’ve got one page to show them not just what you’ve done, but why you care, and that starts by researching who they are and what they value. Mention any mutual connections, keep your language tight, and drop the fluff in favor of clarity that actually gets read. For help shaping a sharp and strategic pitch, this cover letter guide breaks down exactly how to stand out without sounding like a template.

Freelancing Isn’t a Side Hustle Anymore
 
Gig work is no longer a stopgap; it’s a business model. If you want to make this lifestyle work long-term, treat your freelance career like it matters—because it does. That means building a brand, tightening your contracts, staying on top of deadlines, and doing your own taxes (or paying someone who understands digital nomads). Chasing gigs casually won’t cut it anymore, but showing up like a pro every time will start to build momentum.

Community Is the Currency You Don’t See Coming
 
The biggest misconception about being a nomad is that you’re always alone. In reality, the successful ones all seem to find their people in co-working spaces, WhatsApp threads, and city-specific Telegram groups. You’ll need support—especially when a client ghosts or your hostel Wi-Fi dies mid-call—and you’ll find it in conversations with others who get the weird limbo of living out of a carry-on. Prioritize community as much as you do time zones or Airbnb ratings.

Stepping Into the Spotlight as a PR Specialist

If you’re someone who thrives on strategy, storytelling, and the fine art of spin, working in public relations might be your calling card. A PR specialist doesn’t just talk to the media—they shape narratives, guide reputations, and turn even minor wins into headline-worthy moments. From crafting press releases to handling full-blown crisis control, the job is about keeping your client in the public’s good graces no matter what’s happening behind the scenes. For a clearer look at what a PR specialist does, this breakdown lays out the role in a way that’s both practical and motivating.

Your Routine Still Matters, Even on the Road
 
Chasing sunsets feels poetic until your sleep, diet, and productivity go off the rails. A loose but loyal routine keeps you grounded: wake up, work, walk, eat, read, sleep. Without one, you’ll feel like you’re constantly starting over every time you change countries. Don’t underestimate the emotional exhaustion of new beds, new languages, and new noise levels—it’s glamorous until it isn’t, and that’s when a little structure saves you.

Making Time to Read, Seriously
 
Your brain needs a break from Google Docs and Slack threads, and nothing resets your headspace quite like a good book. Reading carves out quiet in a life full of motion, and it can keep you centered when the rest of your world is spinning. If you’re stuck on what to read, I highly recommend poking around My Jamaican Vignettes; their book reviews are thoughtful, reliable, and refreshingly grounded. When everything feels like it’s moving too fast, a great story can slow it all down.

Wi-Fi and SIM Cards Are the Real MVPs
 
You can’t work if you can’t connect, period. Every nomad has a horror story about a late-night client call in a café with flickering Wi-Fi and background salsa music that won’t quit. Do yourself a favor and get comfortable with local SIM cards, eSIMs, and mobile hotspots before you land. A mobile-savvy nomad stays paid, while the one fumbling with their third Starbucks order just for the free Wi-Fi ends up stressed and broke.

Staying Curious About Where You Are
 
It’s easy to fall into the trap of living everywhere and nowhere. You land, find the coworking space, locate the best flat white, and then tune out everything else. But the point of all this wasn’t to live your old life in new weather. The best nomads are curious ones—taking a language class, chatting with a street vendor, learning the politics of the place they’re calling home for a month. The world is your office, sure, but it should also be your teacher.

The digital nomad life isn’t an escape—it’s an exchange. You trade in comfort for curiosity, predictability for presence, and often, stability for story. But if you’re willing to do the work, if you bring the same hustle to your inbox that others bring to their commutes, you’ll earn something a little deeper than a passport full of stamps. You’ll build a life that’s yours, wherever you land next.

Dive into the vibrant world of literature and lifestyle with My Jamaican Vignettes, where every post is a journey through books, wellness, and the art of living beautifully.

Today’s post is a special guest post by Jennifer Scott the founder of the online community Spiritfinder where she offers a safe space to discuss and destigmatise mental health.