How Geography Quietly Shapes Freelance Career Choices
A reflection after a freelancer-to-freelancer conversation
A few days ago, I published a collaborative piece with Steph from The Simple Freelancer.
We called it Four “Bad” Ways of Getting Clients That Actually Work, and the goal was simple: to debunk some of the moral panic around client acquisition and show that different paths can work, even the ones people love to judge.
Illustration by Adriana Danaila
Steph is a freelance home improvement, lifestyle, and commerce writer who relies primarily on cold outreach, networking, and pitching to find clients. She is based in Wisconsin, USA. She started building her business in 2019, after quitting teaching to stay home with her young children. These days, she spends her time typing away, drinking coffee with heavy cream, and running The Simple Freelancer, where she shares practical, no-nonsense advice for freelance writers twice a week. She ended 2025 with around $70K in freelance income—so yes, she really knows what she’s talking about.
(If you’re a freelance writer, you should absolutely subscribe to her Substack.)
I come from a very different place.
I’m a freelance illustrator who built most of my client base through freelance platforms like Upwork and Fiverr, where I’m top-rated. I’m a self-taught illustrator with a business degree, which I genuinely think might be the best degree an artist can have. I’m also the creator of The Gentle Hustle, a growing community for freelance illustrators shaped by my 14 years navigating graphic design, illustration, and independent work. I live in Romania, Eastern Europe.
Same conversation.
Same four methods.
Very different lives.
During our collaboration, we walked through four common ways freelancers get clients and unpacked the myths around each one. But after the post went live, I kept thinking about something we didn’t explicitly name at the time.
At first glance, it looks like our choices come down to personality:
introvert vs extrovert, platforms vs pitching, structure vs spontaneity.
But the more I sat with it, the more I realized something else was shaping those decisions too.
Geography.
Language.
Proximity.
So this piece is a continuation, a few thoughts that only crystallized after the conversation.
Freelance platforms
One thing that stood out to me during our conversation was hearing that Steph also started freelancing on Upwork early on. That alone says a lot about how powerful these platforms actually are.
For Steph, platforms were a starting point. As her confidence grew, she naturally moved toward cold pitching and deeper networking — paths that made sense given her industry, language, and location.
For me, platforms felt almost accidental at first. I genuinely thought I had just stumbled upon Fiverr and Upwork by chance. But looking back now, I don’t think it was random at all.
Freelance platforms flattened geography.
They removed the need for proximity, warm intros, or being “in the room.” They offered structure, payment protection, and global reach — things that mattered deeply when you’re not based in a major creative hub.
What felt like a coincidence was actually the only available option.
Cold pitching
In our original post, we agreed on something important: cold pitching works… if you can tolerate rejection and put in the time.
For a long time, I framed my hesitation around pitching as an introvert–extrovert thing. But I don’t think that’s the full story.
Cold pitching is deeply tied to language, culture, and perceived familiarity. When an editor, marketer, or decision-maker receives an email from someone with a foreign name, a different cultural cadence, or slightly off humor, there’s often more friction, even if the work is good. Not always consciously. But it’s there.
No wonder cold pitching felt synonymous with “awkward” or “spammy” to me for years. I grew up in a part of the world where trust is hard-earned and rarely assumed.
Pitching isn’t just about ideas.
It’s about tone, timing, and sounding like you belong in that inbox.
And Steph is a great example of how powerful pitching can be when those conditions align. She shares a really practical cold-pitching framework in our collaborative piece, which I am 100% stealing.
Referrals and networking
We also talked about how referrals and networking are often seen as something reserved for extroverts with lots of free time.
There’s another layer here too: time zones.
Most networking events, coffee chats, and industry calls are optimized for Western schedules. For someone in Eastern Europe, that often means evenings, late nights, or sacrificing personal time to stay visible in US-centric spaces.
You can do it—I have—but it comes at a cost. It requires rigid scheduling in a lifestyle I intentionally try to keep flexible. Sunny afternoons suddenly turn into Zoom calls. Spontaneity disappears.
So while networking works, it’s not equally lightweight for everyone.
Content creation and personal branding
This is where things get interesting.
Content creation is one of the few ways to bridge geographic distance at scale. It gives people context before you ever speak to them. It lets your thinking travel ahead of you.
For me, content became a way to build trust without proximity, to show how I think, how I work, and what I value before ever reaching out.
For Steph, content is a way of staying top-of-mind and consistently reminding people what she does and what she offers.
And here’s what we both agree on:
Best way to make content is when your income doesn’t depend on it.
Platforms (in my case) and cold pitching (in Steph’s) gave us stability first. Content came later, as an expansion, not a survival strategy. That order matters, and it’s rarely acknowledged in online advice.
What I see differently now
At the beginning, I thought our different client-getting methods came down to personality and preference.
Now, I think it’s more accurate to say this:
Different methods feel accessible depending on where you live, the language you work in, and how close you are to opportunity.
Pitching rewards proximity.
Platforms neutralize distance.
Content builds bridges over time.
None of these paths are superior. They’re contextual.
The mistake isn’t choosing the “wrong” method, it’s ignoring the conditions you’re operating within. And those conditions shift.
So instead of asking “What works best?”
I think a better question is:
What wouldn’t work for my niche, language, cultural background, or lifestyle?
Because the market may be global, but trust, familiarity, and opportunity are still filtered through local lenses.
You can read both mine and Steph’s full perspectives in our original collaborative piece.
Next Week’s Post:
Which freelance platforms are still worth it in 2026
This gave me chills! It's such an insightful look at the conversation through a geographical and cultural lens with nuances that aren't often discussed outright. I'm so happy that our conversation ultimately led to this reflection on these methods.
I read your collaboration piece, but I love how you broke it down here. You are giving very valuable advice, which I wish someone had given me 3 months ago. before I burned out.
Social media, creating content, and showing up too much on socials takes a lot of valuable time that, in the beginning, when you are still testing out strategies, your prices, and leveraging clients, is the worst thing to do.