Interview: How Heather Catherine Orr Achieved Her Dream Of Freelance Copywriting

Haris Halkic: Hi Heather, thanks a lot for agreeing to share your best tips on copywriting and your background. Let’s start with how you got started in copywriting? Please, tell us more about your story.

Heather Catherine Orr: Thank you for inviting me to contribute, Haris. About a decade ago, I stumbled into a job writing web content for a search marketing firm in Los Angeles.

Then I moved to Seattle for a few years and was lucky enough to get an in-house copywriter job in the corporate marketing department of The Seattle Times. While I was there I got the chance to work on my first print ads and see them published in the newspaper and circulated throughout the Pacific Northwest.

I also worked remotely for a small digital marketing firm and Expedia while I was in Seattle. When I returned to Los Angeles, I ended up as an in-house copywriter in the corporate marketing departments of Kaiser Permanente and Farmers Insurance.

But my dream was always to become a full-time freelancer and have control of my own work projects and schedule.

Haris Halkic: How did you transition to freelance copywriting from the job you had before? What specific challenge did you face and what advice would you give to someone in a similar situation?

Heather Catherine Orr: I didn’t transition to freelance copywriting very gracefully. In fact, I got stuck in a limbo for awhile between freelancing and working a full-time job. I tried to sustain myself on just freelancing a couple times and failed. So, I worked full-time while also freelancing here and there on the side.

What I consider my first “real” freelance job came from a company that I had worked for previously as an employee. The owner contacted me later for help with their website copy as a freelancer.

As far as challenges, I had so many transitioning to freelancing that it’s hard to narrow them down. My biggest challenge was trying to start out in Los Angeles, one of the cities known for its high cost of living. So, having a savings to cushion my transition was not really possible. It wasn’t until I was able to relocate to a less expensive area that I was able to buy myself more time and energy to put into freelancing exclusively.

I know a lot of new freelancers probably find themselves in the same position. I wish I had some great advice to give, other than don’t give up.

It’ll eventually happen, if it’s truly your dream. I’ve found that no matter how long it takes, persistence always pays off.

Haris Halkic: Getting clients is one of the greatest challenges for freelance copywriters. Could you talk about how you get clients?

Heather Catherine Orr: Starting out, it was difficult for me to get clients. I didn’t have a large network to tap and I was super confused about what to do. After burning out on endlessly sending proposals for projects on “word mill” sites, I found out about more professional-level job sites like Problogger and got a couple better paying clients there. I also joined Slack and got into chats focused on sharing remote and freelance jobs.

Then I began to contact companies directly using email templates from expert business coaches like Ed Gandia. I also built my website and blog, and began connecting with fellow copywriters on Facebook and LinkedIn. I attended networking events to meet new friends and contacts.

Eventually, people started to send me inquiries through my website and LinkedIn.

Haris Halkic: How did you learn to write copy? Are their teachers, books or resources you can recommend?

Heather Catherine Orr: At first, I mostly learned to write copy on the job. But sometimes this isn’t always the best way, because working in corporate marketing departments can be like drinking from a firehose, especially if you’re the only in-house copywriter, which is often the case.

There can be so much work coming in that it turns into more about how much you can get done and not how well you can get it done. And the results get lost in the shuffle. I felt like the amount and quality of my samples suffered because of it too.

So, I started taking an online course here and there when I could, from sites like Copy Hackers. I also managed to get my hands on John Carlton’s freelance writing course. Besides this, I also read some of the most-recommended books for copywriters, such as Cialdini’s “Influence” and Claude Hopkins’ “My Life in Advertising”.

But I’m always in the process of learning, both in copywriting and for my other interests. I think one of your best resources as a copywriter is maintaining your child-like curiosity and openness about learning new things.

Haris Halkic: How do you prepare for a writing session?

Heather Catherine Orr:

I always prepare for a writing session with as much research as possible. You can’t really write effectively without it.

I ask questions about my client’s business, industry, customers, competition, project goals, etc. I review my client’s previous marketing communications and see what can be improved. And together, we develop a creative brief and both sign off on it, so we’re on the same page from day one.

Depending on the project’s goals, I also gather customer feedback and information to gauge the target audience’s expectations and awareness level of the company and product/service I’m writing for.

Haris Halkic: Who’s your favorite copywriter or favorite piece of copywriting?

Heather Catherine Orr: There’s a TON of copywriters I admire. But the first two that come to mind are Joanna Wiebe and John Carlton as I mentioned previously. Joanna Wiebe is a rock star to me! She always has such awesome tested insights about marketing and copywriting to share. Copy Hackers is a great resource for expanding your conversion copywriting knowledge and experience.

And I recently discovered that John Carlton grew up in the same Southern California city that I did. His blog is a treasure trove of freelance copywriting wit and wisdom. And his “One-legged Golfer” ad is a classic worth taking the time to study.

Haris Halkic: In your opinion, what are the greatest advantages of being a freelance copywriter? What makes this lifestyle so special?

Heather Catherine Orr:

I think the biggest advantage of being a freelance copywriter is being able to choose the projects you work on so you can more purposely shape your career.

And of course, everyone always says traveling, but it’s so true. I recently got the opportunity to work and travel in Mexico. It’s something that I would’ve been unlikely to do as an employee.

Haris Halkic: What one daily habit has contributed to your success more than any other?

Heather Catherine Orr: I’d say that exercise has been my saving grace. As a copywriter, sometimes you spend a lot of the day sitting alone at a computer. It can take a toll on your health and mood.

I’m not perfect at my exercise schedule yet, but I try to make sure that I get in to the gym at least 3-4 times a week. When I can’t get to the gym, I’ll do yoga or take a walk outdoors to refresh myself in nature.

Haris Halkic: If someone wants to hire you, what is the best way to get in touch?

Heather Catherine Orr: You can contact me through my website: or on LinkedIn. Or, you can email me directly at I focus mostly on the health, finance and tech industries, but I’m always open to new opportunities. Feel free to reach out! 😀

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