Updated: Mar 16
Every successful copywriter begins their career the same way: from scratch, with zero experience.
I remember being discouraged early on by how little I knew about copywriting, running a business, and even being a writer. It seemed like everyone online knew how to write powerful copy from day one and knew where to go to find clients, except me. The reality is, all successful copywriters must go through the awkward phase of learning the craft and finding their first clients. You're going to make mistakes, feel like an idiot, and endure some learning curves. I know I have (and sometimes still do).
The good news is, once you push through the initial uncomfortable season, running a copywriting business can turn into a fulfilling career that pays well and gives you daily opportunities to use your creativity to solve real-world problems.
My journey into copywriting started over a decade ago, by complete accident. I wrote this article simply to tell my story. No, this post doesn't contain some secret formula for becoming an in-demand copywriter (but there may be some lessons hidden under the surface).
So, here's how I went from earning minimum wage to becoming a six-figure freelance copywriter.
The accidental volunteer copywriter
I knew from a young age that I wanted to be a writer. Some of my earliest memories are penning my very own Scooby Doo short stories in notebooks (and funnily enough, the blank pages of unused photo albums).
Throughout middle and high school, all my best grades were in English classes. I aced essays. It helped that my parents and several teachers always encouraged me to write. I think they all saw that (1) I loved the craft and (2) was decent at it, so people around me were always gracious and encouraging.
Unlike many aspiring writers, I don’t have some painful memory of an English teacher or parent shooting down my aspirations to become a writer one day. I was fortunate and privileged in that sense.
Many of my close friends knew I loved writing as well. So a few years after graduating high school, my childhood best friend, Joey, took a position at a local nonprofit.
On one of his first days, the founder of the nonprofit, Ryan, asked if Joey knew any good writers. The organization needed someone to blog and write “copy” (a word I hadn’t learned yet).
Joey recommended me.
I didn’t have the first idea of how to write a blog post, website copy, fundraising campaigns, or any of the other material that Ryan needed me to write. But I accepted.
As my dad liked to say, “If someone offers you an opportunity that you’re not qualified for, accept it, and then go learn as much as you can about it.”
I started by writing their blogs. It was a faith-based nonprofit, so many of my articles were about Christianity. The other articles were mostly about the organization and its work in Central America.
In total, I worked for the nonprofit for two years on a volunteer basis. I wrote many blogs, several Kickstarter pages, all the organization’s newsletters, website copy, and even some video scripts.
Word gets around
Most people hate writing. Or at least, they hate writing about things when they’re told to write about them. For some reason, I’ve never minded this.
I enjoy sitting down to write fiction. I also enjoy writing technical blog posts about niche software subjects that only a few hundred people in the world care about.
So, as I wrote for the nonprofit, other people began to hear that I was a willing and capable writer. I began helping friends write and edit college admissions and scholarship essays. Occasionally businesses would ask me to help them find the right words for their website or blog posts. I remember charging $15 per hour.
One day, I found a company on Craigslist looking for an “article writer.” I reached out. They told me that they paid $15 per article. I remember telling them that I would charge $17 per article. They hired me at that rate, and told me I was their highest paid writer.
I wrote a total of one article for them. It took me four hours. And they paid immediately.
Broke and ghosted in Austin
I forgot to mention, everything so far in the story took place in Fort Myers, Florida, where I was raised. During my years volunteering with the nonprofit in my early 20s, I only spent two semesters in college. I worked many odd jobs to pay the bills. Some of my favorites included washing windows and working in a high-end furniture store where I discovered that I am colorblind.
On the side, I began helping a friend with his event startup. I traveled to Toronto, Montreal, several places across Florida, and San Antonio, Texas. We helped put on events for Jordan Belfort (The Wolf of Wall Street), political figures, and religious speakers. Live event logistics was super fun work for a single dude in his early 20s.
After the event in San Antonio, me and some friends traveled to Austin for a couple days. The city stuck in my head. Over the next few months, I felt compelled to move there.
In the months leading up to my move, I was still volunteering for the nonprofit. I decided I’d give writing a chance. What if I could move to Austin and just write full time, I dreamed.
In the weeks leading up to move, a freelance designer asked me to help on the biggest writing project of my life. I was still charging $15 per hour. The timing couldn’t have been better.
I lived off savings (and some help from a family member) for the first few weeks in Austin. I worked from a coffee shop within walking distance of my studio apartment.
One day, the designer broke the bad news to me: the person we’d been working for ghosted us. We weren’t going to get paid. Nearly a month of daily writing work, all for nothing.
I applied to several jobs near my new studio and landed a minimum wage job working at a print shop. Over the next year and a half, as I got to know Austin, I oversaw the front desk, printed papers for UT students, and bound thousands of books, theses, and calendars.
Also, I wrote nearly every morning. On my walk to work (because I didn’t have a car), I left more than an hour early. I’d find a cozy spot on the UT campus and simply write essays, short stories, and poetry before I was expected at work.
Most of what I wrote never saw the light of day. But I did begin to learn about publishing. I got a couple poems published in a small Texas literary magazine. I published some articles in blogs that were hosted and run by friends. And I still wrote for the nonprofit from time to time, though that was beginning to fade once I no longer lived in the same city as the rest of the team.
Oops, I quit my job
I began to feel uneasy at work. By now, I was 23. I had no college degree. While I enjoyed the flexibility of my job, and the freedom to write at work, I was earning less money than I’d ever earned per hour in my adult life.
I began looking for new jobs around Austin. After a few weeks, I had almost nothing to show for it. So I decided to turn up the pressure.
I put in my two weeks’ notice. I figured that the pressure would force me to find a new job.
But it wasn’t a completely random decision. I had already filed my 2015 taxes and knew that I had a return coming my way that equated to a little more than two weeks’ pay. So, between my last paycheck and my tax return, I figured I had a financial runway of about one month to find the next gig.
“Why don’t you just start writing for tech companies?”
I used my new freetime to apply to jobs, bus around town to interviews, and write.
About two weeks in, none of the jobs stuck. I was beginning to feel nervous.
Fortunately, I had a friend whose career had always inspired me. The only throughline for his jobs was that they sounded exciting and fun. He was an entrepreneur multiple times over. He used to be a DJ. He once worked for an author I respected. And even now, he still runs a web design firm and a blog (which I've written for a few times). His name is Aaron.
I invited Aaron to dinner and told him about my situation. I told him I was looking for new job ideas. The first half of our conversation, I told him about all the jobs I’d applied to. Some I was excited about. Some were less exciting, but paid more than I’d been earning at the print shop.
When I’d broken down all my options, Aaron finally shared his opinion. “Alex, you are a good writer. You live in a tech city. All these developers know how to create great products, but they don’t know how to talk about what they’ve created. Why don’t you just start writing for tech companies?”
Freelance copywriter, freelance event hand
The next day, I walked five or so miles to Half Price Books and purchased a couple books about freelance copywriting and entrepreneurship. I was hooked.
I emailed Aaron and told him I’d start freelancing.
I had another friend named Page who ran a small marketing agency. I sent her a Facebook message along with some of my writing samples from the nonprofit. If she needed help with writing, I explained, I would be available to help.
Page hired me instantly. Within a month or so, Aaron referred me to a local tech company. My expenses were low, but even these small projects wouldn’t cover my bills.
Fortunately, SXSW (South by Southwest) 2016 was about to take place in Austin. With my experience working for my friend’s event startup a couple years earlier, I found a company that needed help setting up and dismantling stages for the festival.
Between the handful of copywriting projects from friends and the festival work, my bills were covered for another few weeks.
My working hours were peculiar. After SXSW, the event company kept me on call for various concerts and conferences. Sometimes my work day wouldn’t begin until 11pm. I’d spend all night breaking down stages and not get home until 4 or 6 in the morning.
Meanwhile, I read everything I could get my hands on about copywriting and freelancing. I pored over books and blogs like this one, discovered podcasts, and watched how-to videos on YouTube.
Some of my first copywriting projects from outside my network came from Craigslist, attending networking events, and through websites like Thumbtack and Upwork.
And it worked. In 2016, I basically earned the equivalent of minimum wage again. Except this time, I’d earned that by working for myself as a writer.
Here’s how I got some of my biggest wins that first year:
Through Upwork, I won a weekly blogging contract for a real estate brokerage firm. This created the first predictable paycheck I ever had as a solo copywriter.
I attended a local tech event. Since I didn’t have business cards or a website yet, I focused on collecting as many business cards from other people as I could. When the event was over, I emailed everyone I’d met, and let each of them know I was available for hire. One of them hired me immediately for multiple projects.
Instead of simply browsing writing projects on Craigslist, I drafted posts offering my services. I basically made a free ad for myself as a copywriter. Then I posted the ad in different cities across the U.S. Multiple people—and one magazine—hired me from these simple ads.
(To learn more about writing persuasive copy, get my guide: 11 Copywriting Secrets You Can't Afford to Miss for $7.)
Globe-trotting company of two
A few months after starting my copywriting business in 2016, I also began dating one of my best friends, Sarabeth.
We became serious fast, though it didn’t feel fast to us. By then, we’d known one another for a few years. I proposed to Sarabeth during the week of SXSW 2017 and we began planning a summer wedding.
Sarabeth was a good writer. In fact, even before we dated, Sarabeth and I would join one another in coffee shops for hours of freewriting.
One day I floated an idea to Sarabeth: What if you joined my copywriting business when we get married?
“That’s a terrible idea!” she said, and I dropped the subject for a while. At the time, she was applying to grad school, intent on being an English professor.
One day I won a massive contract on Thumbtack. A local tech company needed tons of marketing collateral, as well as a technical user manual. It was the first time in my copywriting career that I felt overwhelmed by my amount of work.
I asked Sarabeth if she’d help with some editing. I’d write it, she’d edit and proofread.
Sarabeth was quickly hooked, and she liked the work a lot more than other corporate jobs she held since graduating college. As our wedding drew closer, we began dreaming about what we could do if both of us worked from our laptops full time. The dream slowly morphed into a plan.
The week leading up to our wedding was unbelievably busy. We’d decided to travel indefinitely for our honeymoon, which meant that Sarabeth and I had to pack each of our lives into boxes, prepare for our own wedding, and get ready for an indefinite backpacking trip — all at once.
And it worked!
We got married. The next day, we boarded a plane to Costa Rica. We had a proper honeymoon in a nice resort, and then began backpacking. We spent a few weeks exploring Costa Rica, then spent more than a month in Nicaragua. We wrote from our laptops and the business continued to grow.
We returned to the U.S. and lived nomadically for a couple months, visiting family and friends across multiple states. Then we went to Europe for another few months. All in all, we spent about six months traveling, working as digital nomads from our laptops.
We moved back to Texas. We settled for about eight months in Fort Worth before returning to Austin. During our stint in Fort Worth, we decided to niche down.
Until then, Sarabeth and I had accepted any work that came our way. We wrote for real estate firms, tech startups, agencies, clothing brands, and healthcare companies. We even worked for one person who had us write dozens of pages about rain gutters. Those early days had us doing some real glamorous work.
Over time, we started to realize that our favorite clients were all in tech. But one of our biggest clients was a real estate company. So, we started to say that we specialized in tech and real estate. Our work went up almost immediately. Tech companies and real estate companies were everywhere, it turned out. All we had to do was name that specialty—and show those portfolio samples—to get their attention.
A few months later, we dropped the real estate side and decided to double down on tech. Our work went up again. Then we decided that our best clients were an even finer niche within tech: SaaS (software as a service). So we niched down again, and our leads went up.
We also began specializing in specific types of work. We both loved website copywriting. We had learned a lot from direct response copywriting books and blogs about conversion copywriting. So we made website copywriting our core service — and our leads went up yet again.
It’s important to note that every time we niched down, we were terrified. Like genuinely scared. I think we worried that by specializing, we would be turning away more work than we’d be bringing in. But the truth is, when you get to the place where you know the type of clients you want to attract, you should make that niche clear! When those clients come to your website and see their industry expertise reflected back at them, they’re much more likely to hire you.
Learning on the job
Over the years, Sarabeth and I tried to learn skills that businesses find most valuable. Writing in and of itself is a valuable skill. But there are deeper skills within writing that have even greater value.
Sometimes we enrolled in courses. Other times we read books or blogs. With time, I became adept at writing long-form. This translated into SEO blog posts, white papers, case studies, and ebooks.
Sarabeth and I both doubled down on conversion copywriting for websites. And then, in 2019, Sarabeth decided to make the biggest investment we’d ever made in our business. She took UX Design training through General Assembly.
Now, instead of writing for marketing departments, Sarabeth was writing for digital products. Sarabeth is a great copywriter. But content design is where she really found her stride. The Content Design program was far and away the best investment we ever made in the business. Companies began hiring her left and right to draft their in-app UX copy.
And then mid-way through 2021, after four years of freelancing full-time, Sarabeth took a full-time Senior Content Design job working with one of our oldest clients, AppSumo. (She would like to note that she’s super glad she never went to grad school.)
Minimum wage to six figures
As I mentioned, my first year as a copywriter I earned the equivalent of minimum wage. Fortunately, the business grew significantly year over year.
In 2020, for example, Sarabeth and I crossed our 2019 income… by July.
It’s hard to calculate our earnings growth this year since Sarabeth now returned to full-time employment. Obviously I don’t generate the same revenue on my own as Sarabeth and I did together. But nonetheless, I crossed the six figure mark a few weeks ago (not counting Sarabeth’s contributions during the first half this year). We just bought a spacious house in Austin, Texas. We don’t have debt. And we’re able to invest and save for our future.
All because of freelance copywriting.
I remember reading books about copywriting during my first year as a freelancer in 2016. Making a decent living from my words sounded too good to be true. I feel very fortunate to have grown the business to this point. And I’m more excited than ever to see where the business will go in the future.
One of my favorite lessons about freelancing is that time is the magic ingredient. The longer you freelance, the more serendipity carries your business. During my first couple years, I had to actively pursue every new project. No one was looking for me and my business. I had to be proactive to move my business forward every inch.
Now, nearly six years in, almost every new client finds me. I work almost 100% based on referrals, recurring clients, and people stumbling upon my work and portfolio on the web.
When people tell me they want to try freelance copywriting, I like to suggest that they give it at least 3 years. Because with freelancing, the worst parts are frontloaded. Most of the fun bits are reserved for people who stick with it past the challenging first year or two.
Okay, okay, who am I kidding? I loved freelancing from day one. It’s a career that, for me, ages like wine. I still avidly read business and copywriting books, just to stay on top of my game.
Today, I work with clients who pay well and inspire me. Often, I’m hired for my ideas, not just my writing. I’m not merely a writing machine who’s hired to create content for the sake of creating content. I’m an idea person who’s hired to solve real business problems. I’ve moved from the surface level to the strategic level.
If you’re just getting started in this business, I hope you’ll give it a couple years before deciding if it’s the right job for you. Yes, freelance copywriting isn’t for everyone. A lot of talented writers hate it.
But if you’re a writer who’s ever dreamed of working for yourself, becoming an in-demand expert, and seeing your ideas have impact across many companies, then take it from me: Best job I’ve ever had.
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