#GirlsRock: An Interview with Freelance Copywriter Annie Maguire


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I found Annie Maguire in a magazine article.

cd-interviewsTrue story. She’s one of those people you hear stories about. People who quit their 9-to-5 to forge a life on their own terms. Then, she wrote a book about it. Also, she incorporated the word badass into the subtitle, which of course, is badass.

Annie’s story happens where talent, drive, and resourcefulness collide. Today, she’s here to tell about her journey, for #GirlsRock.

#GirlsRock is an occasional series here on Coach Daddy that spotlights women who do cool stuff. Annie definitely qualifies. Her background runs parallel with mine in content marketing – only she absolutely slayed it.

Annie was a campus connection reporter for ESPNU at the University of Connecticut. A former content creator and copywriter, she collected questions readers asked on her blog about freelancing, and, voila, From Full-time to Freelance: Your Guide to Becoming a Badass Freelancer was born.

Please give Annie a warm CD welcome, and be sure to check out her food blog, too, which is also listed in the Official Badass Directory in the Library of Congress.

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Eli: When you were little, what did you think you’d grow up to be?

IMG_0486Annie: Great question! When I was little, I was always doing something, from and reading and writing to drawing, acting, singing, or creating in some way. I didn’t think too much about “what I wanted to be,” and honestly, didn’t really figure it out until after college. Looking back now, it seems obvious that I would eventually become a writer, but when I was little, all I cared about was being creative and using my imagination.

Eli: What were some of the things you dreamed up back then?

Annie: I dreamed up all sorts of things! I loved coming up with stories, especially about animals. I would write about African safaris, unicorns, and horses, cats, bugs … you name it! I would come up with “clubs” and invite members of my family into secret meetings, make up businesses (everything from “Annie’s pet service” to selling handmade origami and cards), build “towns” in my backyard, make up stories to entertain my family and friends, dream up imaginary friends and have conversations with them. I loved creating little worlds in my head and with other people. It was a blast!

Eli: How much do you still do this?

Annie: I still do a lot of it! I get to come up with “stories” for a living as a copywriter, but also on my own, too. I’m currently working on several works of fiction (including two children’s books), and am always thinking of ideas for new products (i.e. – eBooks, online courses, etc.) and exploring my passions like yoga, cooking, and art.

Eli: There has to be some overlap. A kids’ book about a yogi chef, or something?

Annie: You’d think, right?!

The first children’s book is about a mummy that gets lost in a museum looking for “his mummy.” The second is about exposing the “scary sounds” you hear at night (as a kid) as not-so-scary things at all. In terms of my other fiction, it skews a bit sci-fi…that’s still very much a work in progress though!

Eli: What was your early freelance writing life like? Do you remember some of those first assignments?

Annie: My early freelance experience was challenging, not because of the assignments, but because I was working a full-time job for a year while freelancing on the side. I had no life – I worked before and after work, and on the weekends too. My first few projects were cool though. I learned a lot and it’s what I needed to feel confident to quit my job. The first assignment was writing the copy for these two apps (the founder is still one of my clients today) and the other was rewriting the copy for one of the top real estate companies in New York (another client I still work with!).

Eli: What’s the hardest lesson you learned early on?

Annie: The hardest lesson I learned early on … hmm … probably how to have patience. It takes a lot of time to build a business, valuable skills, a reliable client network, etc., so when you’re first starting out and you hit your first “work lull” it can be really jarring. You start to question yourself, your decision to go freelance, and your value, which can be hard, especially if you work on your own. This is an early lesson, but one that you continue to face (and relearn) again and again throughout your career.

Eli: How have you managed the rough patches?

Annie: The rough patches are tough. I personally tend to go through a cycle where at first, I feel hopeful, then anxious and worried, then calm down again once I get some leads or conversations going. I think what’s also helped a lot is having a lot of savings to fall back on. You’re far less stressed out about work and money if you know you’re still able to pay your bills, even if you’re not working at that exact second.

CD: I get it – you’re busy doing your thing. So at what point did it make sense to write a book about it?

Annie: I work part-time for a SaaS company which helps creators sell their online courses and digital downloads (like eBooks). To write really great marketing copy, I wanted to experience what our customers go through when it comes to productizing (creating the product, uploading, marketing, selling, collecting payments, etc.). I had also always wanted to write a book, and felt that starting with something short and “easy to write” would be a good segue. When it came time to pick a topic, I know from working in the “digital product space,” that you want to select something you (a) know a lot about, and (b) a topic which people already think of you as an “authority” on.

For me, this was freelancing – I blog a lot about my experiences as a freelancer, so people constantly ask me questions about it, wondering if freelance is the right choice for them, too. Knowing this, I collected all of the questions people had ever asked me (and made a list of everything I had wanted to know when I first started) and went from there!

CD: What was the suckiest part about writing a book? What was the least suckiest?

Annie: The suckiest part about writing a book was editing. My book is just over 100 pages, so having to reread it over and over again (and still find typos!) was a bit frustrating. I had also promised to launch the book by a certain date, so I felt pressure to condense a lot of the editing/reviewing process into a short period of time. If I were to do it again, I’d either hire a professional editor or write a shorter book!

The most awesome part about writing a book was just getting it written and published! Writing and publishing a book has been on my bucket list forever, so even though it wasn’t necessarily “the book” I had always thought I’d publish, I still felt a heavy sense of accomplishment. It also lifted the fear that was previously holding me back – I would think, “gee, write and publish a book, that’s a lot of work, I don’t know how to get a book cover, and I don’t know how to publish it…” But in reality, it’s not that hard if you have the right software and tools (especially if they’re free).

The whole process was just so much simpler than I had thought, and I think once you “know the ropes” it makes it easier to go back and do it again.

CD: Annie, thanks so much for talking with us today. What would you tell girls out there who think they’d like to write a book someday?

Annie: Don’t be afraid of your voice or sharing your ideas. If you have a natural inclination to write and share stories, there’s a reason for that. You are meant to be a writer, so don’t keep your ideas – no matter how silly or frivolous they may seem–inside your head. Share them with the world! Try not to let “the fear of getting started” or “the fear of failure” stand in your way. The only way to get better and to get your ideas out there is to write and work on them, so until you do it, it’s never going to happen. Also, check out On Writing by Stephen King – it might help you!

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38 thoughts on “#GirlsRock: An Interview with Freelance Copywriter Annie Maguire”

  1. Nice interview!! I love that Annie always had big dreams as a kid and that those ideas were fostered at an early age. Keep dreaming!! I will check out her food blog, I used to have one as well 😉

    1. I’m always mindful of kids’ dreams – my own kids or kids I coach – and that it’s my job to help foster it if I can, right? Or at least not squash it.

    2. Hi Kristi–yes! It’s so important for kids to flex their creative skills and dream big; I know it was huge for me! Thanks so much for the kind words and do please check out the food blog for some recipes. 🙂

  2. Patience is hard for me too! I often feel very self conscience about my writing…so I love her advice! Thanks for sharing!

    1. Thank you so much Julie! Patience really IS a virtue!! I totally get that feeling of being self-conscious, but I like to think of writing like anything else in life: practice makes perfect! I believe wholeheartedly that if I can do it, you can do it too. 🙂

    1. Glad to hear it ksbeth!! Thanks for sharing your thoughts. I completely understand what you mean by “I have no idea where to begin”–I felt that same way for a very long time. May I suggest this article I wrote about how to publish your next eBook in 7 days? The timeline may not work for you (or maybe it will!), but either way, I guarantee you will find helpful information that will teach you exactly how to get it all done! 🙂 https://medium.com/@anniemaguire/write-and-publish-your-ebook-in-7-days-76f41824423b

  3. You always made up the best stories about your animal friends. I remember the plays you use to think up and star in, the words you invented that just rolled off your tongue so naturally and all your adventures and humorous antics. Destined for greatness! So proud of you, Auhnnie.

  4. LOVE this interview! Annie – you are so gracious to share your wisdom and experience. I am in the editing stages of my book, and I totally agree that it is that part that takes the longest. That said, you have inspired me to get up and finish!
    Eli – as always…you rock!

    Ps: Stomperdad sent me over here – sorry that I have been away for so long!

    1. MamaMickTerry thank you SO much! Wow, such sweet and kind words, I really appreciate it. That is SO exciting to hear and I hope you finish your book this month! The world is simply a better and more beautiful place when we all have the energy and means to share our ideas. Thank you for sharing yours!!

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