The earliest written evidence of the word ‘freelance’ comes from Sir Walter Scott’s Ivanhoe, in which a lord refers to his paid army of ‘free lances’–medieval mercenaries who would fight for whichever nation or person paid them the most. Fast forward to today, and the word means something very different. The spirit is similar, but we’ve lost the focus and clear distinction of the meaning.
And that’s not surprising. There’s something exciting about being your own boss—setting your schedule, choosing your clients, and doing work that truly matters to you. But here’s the clarity we’re missing: freelancing isn’t entrepreneurship. And that’s okay.
A lot of freelancers fall into the trap of thinking they need to “level up” into entrepreneurs—hiring staff, scaling operations, and building a business empire. But what if the secret to success isn’t growing bigger, but going deeper? What if freelancing is the destination, not just a stop along the way?
Freelancer vs. Entrepreneur
Imagine you’re a craftsman who builds beautiful custom furniture. As a freelancer, clients come to you for your unique touch. They value you—your hands, your ideas, your craft. The moment you stop working, the work stops.
Entrepreneurs, on the other hand, don’t just build furniture—they build factories. They hire people to do the work and focus on scaling. Their success isn’t tied to their own effort; it’s tied to the systems they create.
Here’s the key difference:
- Freelancers get paid when they show up and create magic.
- Entrepreneurs get paid when their systems produce results—whether they’re involved or not, awake or asleep.
Trying to turn a freelance career into an entrepreneurial venture can create chaos. You hire others to do what you do best, but no one cares as much, works as hard, or delivers at your level. So what happens? You step in to fix it. Suddenly, you’re doing two jobs—leading and executing. And that’s where things start to break down.
Solution? Own your freelance identity. Lean into it and build a structure that allows you to thrive within it.
How to Thrive as a Freelancer:
1. Pick the Right Playing Field
A friend of mine once dreamed of selling custom board games to name-brand toy and game makers, but after months of chasing leads, he realized they weren’t interested in freelancers. The big players had been burned too many times by freelance game designers. On the other hand, independent comic and game shops were thrilled to work with someone like him. Moral of the story? Some industries welcome freelancers, and others don’t. Choose an industry that’s glad you showed up.
2. Serve the Smallest Viable Audience
Forget trying to appeal to the masses. Your best bet? Find a tiny group of people who can’t imagine hiring anyone else but you. Think of the photographer who specializes in engagement shoots at a particular landmark. Clients don’t just want “a photographer” — they want her because she’s the expert in that setting. Find your niche and own it.
3. Stop Racing to the Bottom
If your selling point is being cheaper and faster, you’re setting yourself up for burnout. The race to the bottom is brutal, and the worst part? You might win. Instead, aim to be the freelancer who’s known for “can’t find anywhere else” quality, insight, and reliability. People should say, “Yes, they’re expensive, but they’re worth it.”
4. Build Your Toolkit (and Keep Sharpening It)
Your tools and skills are your superpowers. Whether it’s mastering new software, refining your craft, or learning the art of negotiation, continuous improvement is non-negotiable. But don’t just focus on technical skills—emotional intelligence, communication, and problem-solving matter just as much. Freelancing requires an enormous amount of physical and emotional labor. Consistently honing your skills over time, and remaining curious, are essential ingredients.
5. Prospect Like a Pro
A freelancer without a steady pipeline of work is like a restaurant with an empty fridge. The key? Set aside dedicated time each day to prospect for new opportunities. Whether it’s sharing valuable insights on social media or your personal blog, reaching out to past clients, or attending targeted events—keep planting seeds so future work has the opportunity to grow.
6. Create a Category of One
Position yourself in a way that makes you irreplaceable. Instead of saying, “I’m a graphic designer,” say, “I help wellness brands build compelling visual stories that resonate with their customers.” When you define yourself uniquely, clients won’t shop around—they’ll come straight to you. As Zig Ziglar said, be a meaningful specific; not a wandering generality.
Drawing the Line: What’s Free and What’s Not
Everyone loves free stuff—but as a freelancer, you can’t give away everything. The trick? Be generous with your knowledge, but clear on your boundaries. Maybe you offer free insights through blog posts or webinars, but your core service—your expertise—comes at a price. Clients need to know your value, and more importantly, you need to believe in it yourself.
Learn to say ‘No’ with confidence. Not every opportunity is a good fit, and it’s okay to walk away when the value isn’t there.
Upgrading Your Clients
You almost certainly know this already: Not all clients are created equal. The fastest way to elevate your freelance career? Replace bad clients with better ones.
Signs of great clients:
- They respect your process.
- They pay on time.
- They value expertise over a bargain.
The better your clients, the better your work, and the better your reputation. Start making room for the right opportunities by saying no to the wrong ones.
Own Your Freelance Career
Freelancing isn’t always (and doesn’t have to be) a stepping stone to something “bigger.” For many, it is the destination—if you do it right.
You don’t have to scale, hire, or become an entrepreneur to be successful. Instead, focus on becoming excellent at your craft, serving the right clients, and structuring your work to support your life.
