Freelance Copywriter Success Stories: Real-Life Lessons

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If you’ve found your way to this page, you’re likely seeking inspiration to become a successful freelance copywriter. You’re in the right place!

In this article, I’ll share with you the stories of two successful freelance copywriters, explaining how they began their journeys and built their personal brands.

We will examine the challenges they faced and how they overcame them, concluding each story with key lessons learned. This way, you can start learning from their experiences right away.


I dabbled in copywriting from 2012 to 2017 before transitioning to business management. Even though I wrote in two different languages, I wouldn’t call myself an expert.

Recently, after starting this blog, I renewed my interest in copywriting, learning from the best in the field. This approach has been incredibly effective and time-saving.

Instead of enduring the trial-and-error process yourself, you can simply study freelance copywriter success stories and learn from their mistakes and challenges. Plus, they always have free advice to share with you!

Let’s start with the first one:

Story 1: Joanna Wiebe Success Story

Own your skills and you will help businesses grow

Founder of Copyhackers, Joanna Wiebe is known as the original conversion copywriter.

After earning an English degree, she moved to Japan where she started preparing for the LSAT exam. Although she was admitted to law school, a challenging moment in her life led her to abandon her legal aspirations. She suddenly lost her father.

She says in an interview with The Copywriter Club:

“I took the LSAT and I got into law school. It was actually the night before, the night before my first day of law school my dad died, the night before. I emailed the U of A where I was going and just said like, “Hey, this happened. I’m still going to come,” but I’m like, “This just happened,” and they were like, “Cool, no worries.” They were all very good and the profs pulled me aside after. It was a very nice thing. But I decided after the second day it was just, I was a mess. My dad was like everything to me.”

One day, a friend suggested she try working as a creative writer for an agency. Despite knowing little about the role, she accepted the job.

At that time, one of her main struggles was understanding the concept of “clear over clever” in copywriting, which essentially means prioritizing clarity in your writing rather than crafting complicated content.

Many beginners believe that using complex vocabulary and elaborate styles will impress the reader. However, in copywriting, the goal isn’t to impress but to sell.

Joanna Wiebe’s says that her real transformation began when she joined Intuit, where she focused more on direct response and conversion copywriting, learning how to drive results and improve her skills.

She explains:

“Then you start writing copy as a creative writer which rule number one is clear over clever. To go there, it was really good for tag lines and coming up with concepts, but not for actually closing stuff. For small businesses that want to land business, it wasn’t the best approach. It wasn’t until I went to Intuit about two years later that I took on the role of being a copywriter and then focused more on conversion and learning a lot more about direct response, copywriting, and how to apply that kind of stuff to what we’re doing today online and in email. That’s kind of my story.”

A series of Joanna’s personal experiences, such as overcoming skin confidence issues as a teenager, contributed to her empathetic approach in helping other copywriters build their confidence. She emphasizes the importance of owning one’s skills and understanding the value they bring to table.

Lessons Learned From Joanna Wiebe

  • Control the Client Process: Act as the expert by setting agendas, controlling meetings, and guiding clients through the review process to avoid unhelpful feedback.
  • Focus on Results: Prioritize clear, conversion-focused copy over creative but ineffective writing. Demonstrating tangible results helps command higher rates.
  • Specialize and Promote: Establish expertise in a specific area, create valuable content, and seize promotional opportunities to build a strong personal brand.
  • Value and Pricing: Set higher project rates to attract serious clients and ensure your work is valued and implemented effectively.

For Joanna, being a freelancer means juggling multiple roles, wearing multiple hats, and it’s crucial to define what you want to focus on. Copywriters are always eager to learn new techniques and strategies, but the challenge often lies beyond their writing skills. It’s about managing the business side effectively and ensuring they don’t let others control their process.

In general, copywriters often face the issue of letting clients control the copy process. This can lead to a situation where feedback is based on personal preferences rather than strategic goals. This is why copywriters must educate clients on proper review processes and assert control over their work to maintain its quality and purpose.

Failing to control client interactions from the start can result in a lack of direction and unhelpful feedback. She thinks it’s essential to run meetings, set agendas, and guide clients through the copywriting process. This way, copywriters can prevent clients from making misguided suggestions and ensure the final copy aligns with professional standards and objectives.

She also recommends focusing on conversion and results instead of writing for the sake of writing.

And in terms of pricing, she recommends using high rates to avoid working with clients who are more likely to be a source of issues. (and freelancers know what that means 🙂

Story 2: Ashlyn Carter Success Story

“Even if your visuals slay, it’s the science behind that gets them to put down their card—or not”

For those unfamiliar, Ashlyn Carter is the founder of Ashlyn Writes, a prominent copywriter, and content strategist.

Her LinkedIn profile reveals a career in Public Relations from 2008 to 2016, alongside a role as a news and magazine editor in 2009-2010.

You can see how this was a typical Freelance Copywriter career before the big shift in her life.

In January 2016, she established Ashlyn Writes, stating:

“Even after 120+ clients, 15,434+ students, clocking time crafting dozens of launch campaigns hitting around $18M in combined revenue, & selling more than 1.26M in our agency services alone, I firmly believe working from a place of rest (not hustle) IS possible—and we want the same for you.”

On the question of what motivated her to start her own business, she says:

“I wanted to get out of corporate life even though I loved it and it served me really well for the time I was in it. I had recently gotten out of partial hospitalization for some mental health issues and I knew that I wanted to set up things for myself and not work for other people. I wanted freedom essentially to do my own thing and make money doing it.”

On the challenges Ashlyn Carter faces while running her business, she talks about how hard it is to say “no, we can’t participate in that right now” to 90% of the day to opportunities.

Niche down to blow up

Ashlyn explains the power of niching down to gain traction. “You’ve heard of niching before, everybody has. But I just truly believe that is how you gain traction” she says.

Her strategy is not being confined to a single niche. While she supports expanding services and exploring other areas, she believes this should come after achieving excellence in one specific niche.

Lessons Learned From Ashlyn Carter

  • Effective Copywriting: Persuasive copywriting is essential for creative business owners. Clear and simple language often works better than overly clever wording.
  • Develop a copywriting toolbox that includes a brand voice guide, target audience research, and a swipe file of effective phrases. Use these resources to create compelling and consistent messaging across all platforms​ (Ashlyn Writes)​.
  • Client Communication: When presenting copy to clients, send it an hour before the meeting and review it together during the meeting. Provide a structured process for feedback to ensure that revisions align with strategic goals rather than personal preferences​ (Ashlyn Writes)​.
  • Balancing Creativity and Sales: Focus on communicating value in your copy by addressing functional, emotional, and social impact elements that resonate with your audience. Use simple yet powerful phrases that convey your message clearly and persuasively​ (Ashlyn Writes)​.

These were the main two freelance copywriter success stories for today. I hope you found the information valuable and feel equipped to start your own career as a freelance copywriter.

Ready to start freelancing? Grab your copy of “The Seine Scope Strategy” to learn how to start and grow your freelance copywriting business today!