Kayla Dean, creative brand copywriter and founder of The Literary Co., is a self-made freelance writer who designed her own career after the hunt for a full-time job didn’t meet her expectations. She wasn’t about to let this minor setback stop her.

She claimed opportunities and honed essential skills along the way, focusing on the feedback of editors and mentors. Kayla is proof that you don’t need to have “all of the experience” before you dive in and take control of your career.

If you’ve been dreaming about launching your own freelance writing career, check out Kayla’s story for a dose of inspiration. Not only is she a role model for all self-made writers out there, but she has some career-changing advice for you, too.

Freelance Writing Cafe: What was the #1 reason you decided to start freelancing?
Kayla Dean: I got my MA in English and needed a full-time job but wasn’t finding what I was looking for. I wanted to write full time and felt I could work on my own terms and make the income I wanted working for myself instead of someone else.

How did your freelance journey begin?
In college, I had a lot of internships. My first one was with a swimwear company where I wrote blogs and product descriptions. My second one at a local alt-weekly was truly formative for me. Even though there was a lot of transcription, fact-checking, and proofreading, the editors there mentored me and gave me so many opportunities to write pieces for the magazine.

As an English major, I didn’t get the journalism basics in college but learned it from the amazing people who guided me at my second internship. They were so awesome they even let me freelance after the fact! From there, this boosted my confidence. I invested in a pitching workshop so I could learn how to write successful pitches to magazines and publications, which helped me land pieces in great publications like Electric Literature, Darling Magazine, Bustle, and Create & Cultivate.

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In grad school, I had an amazing opportunity to work with the literary magazine The Believer. They were amazing, and I had the chance to be a fiction reader and even publish some pieces in the magazine. During this time, I also taught college composition, business writing, and worked in a writing center while I was taking classes. This got me used to working with other people and workshopping writing.

When I graduated from my MA in English in 2018, I knew I had lots of writing experience but wasn’t sure how to go full-time. Up until that point, I had done a lot of free writing and internships but hadn’t truly made it into a career. I pitched publications and started reaching out to people in Facebook groups who needed copywriting.

Before I knew it, I was networking on social media, which is where I found many of my clients. I’ve had my business for two years now. It started out as a personal brand but then I evolved it into a copywriting studio. Right now, it’s just me but I’m loving being a business with an LLC.


What is the most important lesson you’ve learned so far? 
Don’t be so hard on yourself. Keep learning. When you get started, there’s going to be a lot you don’t know. The best thing you can do is keep reading, practicing, and learning from others.

What is something you still struggle with as a freelance writer?
Imposter syndrome is a huge one for me! I’ve been writing for 6 years and been full-time for two but still worry that clients won’t like my work! It can be intense sometimes to worry about what I perceive to be others’ expectations. Most of the time, though, it’s imagined. As you get more experienced, you’ll get more freedom to choose your clients so you don’t always have to worry about this.

What advice would you give to freelancers who are just starting out? 
Get your writing out there. Even if you’re not quite sure what it is you want to write, just start writing. If you want to get your feet wet before submitting to publications, post on Medium or create a blog. Then reach out to online magazines, publications, businesses, etc, to start expanding your reach. I’d also recommend growing your community on Instagram. That’s where everything happens! Finally, get an LLC if you’re serious about going full-time. It will protect you and also make you look legit.


What is your favorite thing about freelancing? 
I love choosing who I work with, creating inspiring content that helps people, and getting to write from my own workspace every day.

What is your favorite app, tool, or tip for productivity? 
I use Asana, Google Calendar, Honeybook, and Calendly in my business. They are HUGE time-savers because they keep my to-do lists organized, help me plan my week, keep my contracts & payments in order, and make scheduling meetings super easy.

Do you have a go-to mantra or quote that keeps you inspired? 
“That dream in your heart was planted for a reason.” I used to resist the idea that we can do the things that we dream of. I’ve felt negative in the past and worried that the things I wanted to accomplish in my life were too unattainable or always out of reach, where if you begin to change that mindset and believe things are possible for you, you can make those first steps a little lighter.

What’s your favorite hot beverage to sip while working? 
Peach green tea



Be sure to follow Kayla on Instagram and check out her website: theliterary.co

Want more inspiration? Read more from our Drinking Coffee With Writers series.


☕️Drinking Coffee With Writers is here to give you a dose of inspiration and actionable tips for the week ahead. We’re showcasing freelance writers who are designing their careers and living life on their own terms.  Want to be our next featured writer? Drop us a line at info@freelancewritingcafe.com


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