How To Make Money Writing With The Right Mindset – Interview With Rose Womelsdorf

Haris Halkic: Hi Rose and thank you so much 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.

Rose Womelsdorf: Hey, Haris!

Likewise, thanks for reaching out to me and having me on for an interview. Chatting about writing is one of my favorite things to do, so I’m happy to oblige.

The first time I realized that “copywriting was a thing,” I was a sad, discouraged senior at Johns Hopkins University, wondering what on earth I was going to do with my degree in creative writing & theatre when I graduated.

Sitting on my airbed, noodling around on Google, searching “HOW TO MAKE MONEY WRITING,” I stumbled on Laura Belgray’s website.

Started reading her words, thinking, “wow… this lady is doing a really cool thing… she looks happy with her life… maybe I could learn to do that… nah, I’d probably fail…” and I put it out of my mind.

Never forgot about it completely, but I stood in my own way for a long time, because I had this idea in my head about creative work being something that led you straight to the poorhouse. I thought you had to be lucky to “make it.”

Needless to say, I’ve since let go of that line of thinking!

Haris Halkic: How did you transition to freelance copywriting from your previous job? What’s your best piece of advice for someone who is employed and wants to become a freelance copywriter?

Rose Womelsdorf: My transition began well over a year before I left my day job. I realized I wasn’t making good use of my degree, so I started researching, learning about running a business online, consuming content on marketing and copywriting. However, after several months, I realized I’d been doing a lot of reading and not much writing, and that it was now or never. I began slowly taking on client work while still employed full-time, gaining bits of experience.

Those first few gigs were a serious turning point—it was like, “oh sh*t—it’s true, you really CAN make money doing this!! I was wrong, and I’m so happy!!”

I put in my notice at my 9-5 and decided that I was going to make it work, no matter what. My previous position was at a relatively small local company, so I stayed on for several extra weeks after I broke the news, in order to help train a replacement for my role on the team. I left on great terms with them.

Another key transition step I should mention here is saving money. Once I knew for sure that I was going to transition out of a traditional day job and into building my own copywriting business, I started preparing a nice cushion for myself. Having a healthy stash of cash on hand helps to keep your mind in the right place when you’re just starting out.

Haris Halkic: Getting clients is one of the greatest challenges for freelance copywriters. What ways do you use to get clients?

Rose Womelsdorf: Cold emailing, networking, (local & online), and referrals. Once in a while I’ll check if there’s something fun on the job boards. I like to mix it up.

Also, I’d argue that the greatest challenge for people who own their own copywriting business is not “getting clients.”

The true hurdle is having the guts and the discipline to keep going after clients, keep putting yourself out there, even when you doubt yourself or when you have a lot on your plate already.

Put another way, if you let yourself get paralyzed by self-doubt, or overwhelmed by your current workload, then you won’t market yourself. And if you do somehow manage to send a pitch or two in that state, you won’t come across as an expert, and you won’t land the clients.

So just have faith in yourself, and keep at it. Slow and steady. Sounds new-agey, but the real barrier between you and “getting clients” is often in your own mind.

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

Rose Womelsdorf: Well, I was one of those dweeby little kids who was constantly reading a book under her desk, looking up to answer questions only when called on. I’d go through several books in a week.

My teachers let me get away with it, bless ‘em, because I didn’t cause trouble and I got good grades. Even used to read during band. Any time I had a rest of more than eight measures or so, I’d put my trumpet aside and pick up my novel.

So I was born a total word nerd. Reading and writing were fun and exciting for me from a very young age, and I liked to experiment. Dense research papers were… okay… (lies; I despise them), but I always preferred to write with personality and pep, the way that we speak naturally. Been stubbornly starting sentences with conjunctions and peppering punchy fragments all over my paragraphs since I was about seven years old.

Again, bless ‘em, my teachers and professors let me get away with my grammar shenanigans for the most part. Not sure why, but I’m grateful. Because that meant when I started learning to write copy as an adult, I didn’t have to work against an overly stiff, trained-in, academic writing style from years of formal education. I had always been the loose cannon in lit class. Now I had a direction to aim for.

And now…  specific resource speed round!

Web Content:

Actual, Real Live Books:

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

Rose Womelsdorf: Hmm.

Where’s that gif of Shia LaBeouf screeching “JUST DO IT.”

Kidding aside, my best writing days happen when I keep things simple. Get up, go through my usual morning routine, and jump in.

Of course, some things need to happen before that writing session even starts—research, taking notes, communicating with the client—but the writing itself is more or less straightforward.

My philosophy is to get something down on the page. Edit later. You have to start with something. Even if it’s mediocre, it’s better than having a blank page at the end of the day.

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

Rose Womelsdorf: Okay… THAT’S not fair. I can’t play favorites!

But hey, extra-special-shout-out to Laura Belgray. The one who planted the copywriting seed in my brain in the first place, and an all-around delightful human being.

Other favs, each uniquely fabulous: Hillary Weiss, Tarzan Kay, Apryl Beverly, Ash Ambirge, Jon Buchan, Lianna Patch, Amber Brooks, Satya Kothimangalam.

Moving along to actual pieces of copywriting… I am downright fascinated by sales pages. I’ve got a swipe file full that I admire for inspiration. As well, I love reading good marketing emails and launch copy. Kinda geeky, but whenever I subscribe to a new email list, I save everything in folders, organized, so that I can go back to read through the sequence if it turns out to be good.

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

Rose Womelsdorf:

Marketing and copywriting, at its core, is just connecting folks who need things with folks who can provide them. It’s getting people excited about something that can benefit them.

Building the bridge between a product or service, and the people who will have their lives improved by that product or service.

Seems corny, but it’s true. And it’s really rewarding to be a part of that process.

Beyond that…I love having control over my days and my income. My destiny is in my hands, and that’s thrilling. Being able to work from anywhere is fantastic, as is having extra flexibility to travel and spend time with family & friends when and where I want.

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

Rose Womelsdorf: This may sound silly and fundamental, but SLEEP.

I am ferocious about making sure that I get enough of it regularly. Most people wear a fitness tracker to ensure they get enough exercise every day. Mine is for tracking rest.

Sometimes folks choose to make sleep less of a priority—usually those who are overly in love with the “hustle” culture. Make no mistake: I am not opposed to hard work, and I do believe that hustling has its place, but I will not sacrifice rest. Taking care of my body is essential for brain function, and it ensures that I do my best work.

On a related note, I limit my caffeine intake. There was once a time in my life when I’d drink coffee non-stop, but I’m down to two cups a day. Not even particularly strong coffee, either. These days, I brew it weak and throw in a few ice cubes.

Regardless of strength or quantity, I cut off caffeine intake after around 4:30 pm. That way when the time comes to wind down, I’m ready.

A lot of entrepreneurs talk up the importance of solid morning and evening routines, and those are key for me as well, but if there aren’t enough hours in between those two routines in the first place, I will not be a happy human.

(Wow. Huh. I sound like a boring old lady. I SWEAR, I’M FUN AT PARTIES.)

Haris Halkic: Are there areas you specialize in as a copywriter and if someone wants to hire you, what is the best way to get in touch?

Rose Womelsdorf: Currently focusing on personality-packed web & funnel copy for solopreneurs with a sense of humor and charm, but I’m always open to interesting projects. 😉

My website is rosiethewriterer.com—from there, you can stalk all my socials, email me, or just click “get in touch” to do so.

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