I recently caught up with an in-house copywriter I’ve known for several years. He asked how my business was going, and I told him about some of my projects.
Then I flipped the question back on him, “Have you ever thought about freelancing?”
Turns out, he’d freelanced once for a couple years but ultimately decided the career didn’t suit him. He hated the stress of constantly looking for the next client, living on variable income, and juggling the constant admin of running a one-person business.
I get it. In fact, this is a common experience I hear from full-time writers: They try freelancing for 1-3 years, decide it’s too much work for too little reward, and soon return to a 9-5.
Here’s the catch: Yes, freelancing is stressful, but I think what many freelancers miss is that those first two or three years are by far the hardest ones. You experience all the burden and none of the upside. The real rewards of freelancing—good pay, flexibility, consistent income—come to those who stick it out.
The delayed rewards of freelancing
I want to be careful here because I know there are a lot of “gurus” out there selling freelancing as a get-rich-quick scheme. If something sounds too good to be true, then it is.
Freelancing success is never guaranteed. The career isn’t for everyone. For every six-figure freelancer you read about on the internet, there are probably dozens of great writers who struggle to eke out a decent living.
With that important caveat out of the way, here’s the odd reality about freelancing: Your first two years in business are a bad forward indicator of your long-term potential as a solo writer. Those years are disproportionately difficult.
In the early years, everyone is still learning the ropes. You don’t have a reputation. You haven’t dabbled long enough to learn what type of marketing works for your business. You’re still learning how to manage your day and be consistently productive without a boss.
All of those skills take time to learn.
On the flip side, the rewards of freelancing are delayed. Anecdotally speaking, I earned more in my fourth year in business than the first two years combined. I’ve used freelancing to…
Earn a six-figure income working from home
Spend months each year traveling because of work flexibility
Work with inspiring CEOs and marketing teams
Turn my lifelong love for writing into a strong creative career
Save for retirement, get a mortgage, and develop in-demand marketing skills
… But I didn’t see most of these rewards until after the first two or three years in business.
These “perks” were the result of putting in the time to build a personal marketing engine and foster a reputation for quality.
What separates freelancers who last from those who don’t
Some freelance success comes down to luck—that’s a given. But there are also deliberate steps you can take to improve your odds, and that’s where I want to focus for the remainder of this article.
Plenty has been written about freelancing, but I’ve narrowed this down to seven less obvious habits that have worked for me and for other long-term freelancers I know. If you can internalize these, they might help you push past the tough early years and build something sustainable.
1. Out-advertise the feast-and-famine lifestyle
One of the first adages I learned about freelancing was "feast or famine." Work comes in waves—one month you're buried, and the next you're panicking about bills. But the cycle isn’t inevitable. It’s often a self-inflicted problem.
Most freelancers stop marketing when they're busy. Then, when work dries up, they scramble to find new clients. The best freelancers step above this by maintaining a steady drumbeat of visibility.
If you rely on inbound leads, build a content calendar and publish consistently.
If cold outreach works for you, set a daily or weekly habit for pitching new prospects.
If networking brings in work, don’t disappear when you're busy. Keep showing up to local events.
You don't have to do all of these, but you do need to pick something and stick to it. Successful freelancers eliminate feast-or-famine by staying visible and booking work in advance.
2. Write like you’re worth $1,000 (even if you’re only getting $100)
Many freelancers think they’ll raise their quality once they start getting premium rates. They have it backward. High-paying clients don’t reward potential—they pay for proven excellence.
If you want to earn top-tier rates, start delivering at that level long before anyone offers to pay you for it. Treat every project as if it’s a high-stakes opportunity. That means:
Research deeper. Go beyond the obvious to find unique insights.
Edit ruthlessly. Cut the fluff, clarify ideas, and polish until it shines.
Package professionally. Don’t just deliver a Google doc—format it, include recommendations, and make it easy for the client to see your value.
Freelancers who break through don’t wait for better pay to do their best work. They do their best work first, and the money catches up.
You earn higher-paying projects by first deserving higher-paying work through a stellar portfolio.
3. Take ownership—don’t wait for orders
The best freelancers aren’t task-takers. They’re problem-solvers. Clients don’t want to micromanage—they want someone who will handle the job better than they could themselves.
That starts in the first conversation. Instead of waiting for a client to explain exactly what they need, lead the discussion. Ask about their goals, challenges, and the bigger picture. Then make recommendations. When you take ownership:
Clients trust you more. They see you as an expert, not just a worker.
You get better projects. People want to work with those who care.
You raise your earning potential. Clients pay more for strategic partners than order-takers.
If you just do what you're told, you’ll always be seen as an interchangeable contractor. If you take ownership, you’ll become an indispensable partner.
4. Take advantage of variable income
Freelancing comes with financial uncertainty—but that uncertainty can be a powerful wealth- and business-building tool if you structure your money correctly.
The key is to separate you from your business:
Don’t treat every payment like personal income. Set up a business account, pay yourself a salary, and keep the rest for taxes and reinvestment.
Save aggressively when times are good. This gives you the freedom to say no to bad clients and risky projects.
Think long-term. Use the flexibility of freelancing to make financial moves that salaried workers can’t—like front-loading retirement contributions or taking weeks off without asking for permission.
Freelancers who last don’t just make money. They build a financial cushion that gives them the freedom to take on even better projects in the future.
5. Systematize and templatize recurring tasks
Most freelancers waste time reinventing the wheel. Instead of starting from scratch every time, build systems:
Use templates for proposals, invoices, and contracts.
Develop repeatable workflows for common projects.
Automate admin work where possible (e.g., canned email responses, scheduling tools, bookkeeping software).
The more you systematize, the more time you free up for higher-value work. And the faster you work, the higher your effective hourly rate.
6. Track your continuous improvement
A mistake I made in the beginning was thinking that as long as I write well, I’m set. That’s not true if you want to reach the highest levels. Business owners are counting on you to understand marketing, persuasion, advertising best practices, and more. You’re not just a craftsperson. You’re an expert solving real business problems.
Creative freelancers should think more like software developers: always learning, evolving, and sharpening their skills. For writers, a few high-impact skills to develop include content strategy, SEO, and conversion principles.
Improving your skills is one piece of the puzzle. The other is taking smart risks. That’s where making strategic bets comes in.
7. Keep making bets
Freelancing requires consistency and reinvention. While stability in your core business is essential, you must also try new things to stay sharp and avoid burnout.
Think of every move as a bet:
Every blog post is an experiment to grow your audience.
Every pitch is a test to refine your offer.
Every new service or product is a potential future income stream.
I track the experiments I’m running in a spreadsheet to make sure I’m constantly evolving and putting myself out there.
For example, last year I pitched an article to Adweek, which they promptly accepted and published. I also applied for a press badge at a major industry conference, and I was awarded a free ticket worth over $5,000.
These “experiments” open new opportunities. They also keep my work (which might be mundane on any given day) interesting for the long term.
Freelancing is hardest in the first few years. You are building a reputation, learning how to market yourself, and figuring out pricing. Many quit before reaching the stage where income stabilizes and better clients seek them out. If you stick with it, freelancing can become more than a temporary gig—it can be a fulfilling career.
