Welcome to another installment of the Drinking Coffee With Writers series! We’re featuring writers from our community who have insight to share on their unique freelance journeys.

This week we’re chatting with Austen Tosone, a fashion and beauty writer and the founder of Keep Calm and Chiffon. She carved out her own freelance path after being laid off from full-time jobs at two major magazines. If you’re feeling a bit down this week and need some inspiration to make your own rules, don’t miss this interview!

Keep scrolling for Austen’s top tips for fellow freelancer writers, including why you should be celebrating your those dreaded rejection letters…

Freelance Writing Cafe: What was the #1 reason you decided to start freelancing?
Austen Tosone: Curiosity! I had always wondered what it would be like to write from cafés instead of offices.

Can you tell us how your freelance writing journey began?
I was laid off from a full-time job at Interview magazine and had previously been laid off from my first job at Nylon magazine. I was still interviewing for jobs and started freelancing on the side. I made a list of every editor friend I had and reached out to let them know I was around to take on freelance assignments and I began to jot down any ideas, good and bad, that I thought I could pitch.

I started cold pitching the day after I lost my job and landed my first piece in Fashionista. It was actually inspired by a blog post I wrote for myself (I’ve had my fashion and beauty blog Keep Calm and Chiffon for 8 years!) about what working in retail taught me about fashion. The piece involved me interviewing other fashion editors who got their start in retail. I didn’t have a connection there, but I emailed the editor who sent me feedback on a few pitches (which were rejected) before she agreed to commission this one.

What is the most important lesson you’ve learned so far?
Rejection is actually a good sign. If you sent a pitch and received a “no” from an editor, you have the opportunity to ask for feedback and land more pitches next time. Also, include a kill fee in your contract. You never know.

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What is something you still struggle with as a fashion and beauty writer?
Coming up with ideas that are relevant and haven’t been covered 900 times already.

What advice would you give to freelancers who are just starting out?
No publication is too small to start out with! Start with local newspapers or indie blogs with paid assignments and work your way up to national publications. It’s also helpful to have samples to send editors, so even self-publishing a blog post or two can be good to send along with pitches. When you do this, the editor can get a feel for your writing style.

What is your favorite thing about freelancing?
I was full-time freelance for 1.5 years which gave me tons of flexibility in terms of what projects I would take on and now that I only freelance occasionally on the side of my full-time role at Jumprope I can be even more selective with any assignments I want to take on.

What is your favorite app, tool, or tip for productivity?
I actually wrote a whole blog post about my favorite tools for organization and streamlining my content. I would definitely say to put placeholder deadlines in your calendar a day or two before the real deadline in order to stay on track.

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Do you have a go-to mantra or quote that keeps you inspired?
Just start!

What’s your favorite hot beverage to sip while working?
Black coffee—so boring!

How do you find the motivation to work when you’re distracted or having a bad day?
I do any small task that can move me forward. Momentum can build from that.

What is your favorite place to travel to?
When this is all over I’d love to go to Portugal!


Check out Austen’s writing website and be sure to follow her on Instagram to keep up with her latest adventures!

☕️ 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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