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Behind the Business: Freelance Writer and Content Creator Austen Tosone

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Photo by Jessie Alcheh

Austen Tosone is a woman who wears many hats. She’s a blogger (she started her blog Keep Calm and Chiffon in 2012), an editor, a content creator, an influencer, and a freelancer just to name a few. In a world that seems to be rooting for the death of print media, Austen found her way into freelancing amidst experiencing industry layoffs and has never looked back.

Austen is a cherished member of the Social Sunday team, working as editor of this blog along with being our resident copywriter, but you can also find her byline in several popular publications such as The Cut and Fashionista. One of the greatest things about Austen is her willingness to share her knowledge on the industry along with what it’s really like to live the freelance life. Her real approach to sharing her life with the world (check out her Instagram stories), makes her extremely relatable. This relatability has helped foster an audience that not only enjoys taking fashion advice from her, but also career advice. Read on to learn more about Austen’s informative e-book, the challenges of being your own boss, and the exciting things she has planned for the rest of the year.

Q: For those reading who are new to you, can you tell them a little bit about yourself?
A: I’m Austen, a New York City-based freelance writer and fashion and beauty content creator. I write stories for publications like Fashionista, Refinery29, and The Zoe Report among others, and I create fashion, beauty, and lifestyle content for my blog, Keep Calm and Chiffon, as well as my YouTube channel every week. I also serve as Social Sunday’s blog editor and copywriter. I’m also a lover of cycling classes, craft beer, and long walks along the NYC waterfront.

Q. How did you first get your start freelancing?
A: I originally started out in editorial, working as an editor for both Nylon and Interview magazines, and after experiencing industry layoffs decided to give full-time freelancing a shot. I was still applying for other full-time positions but after getting a few repeat clients, I became confident that I could actually make freelancing work for me.



Q. We know firsthand that the life of a entrepreneur means an ever changing schedule, but if you had to describe a typical day in your life, how would you?
A: It’s true that every day is different but there is definitely more of a routine to my life than people might expect! I’m up by 7:30am every morning and there is always a list of things that I have to do each week. For the blog I know I have to create one post, two videos, and my Sunday newsletter, for Social Sunday I’ll have two blog posts to edit, some email copy to write, and maybe a few product descriptions—so already anticipating a set amount of work each week is really helpful for scheduling. Then I have to factor in other one-off projects like campaigns for social media, creative consulting, writing an article for a national publication, and other types of content creation.

Since I work alone, I like to try to schedule coffee with a friend or something after work to add some human interaction to my day. I definitely work some weekends depending on my workflow, but have been trying be good about being done with what I have to do when my boyfriend gets home from work so we can go to the gym, cook dinner, or just hang out. You have to learn to be both a good employee and a good boss.

Q. Can you share an aspect of your job that might be surprising to others?
A: I think that the biggest hesitation people have about freelancing is giving up consistency—in terms of both routine and income. One thing that I’ve learned from other freelancers is that many have clients on monthly retainer, meaning they have a set rate and scope of work for each month that they’ll be expected to complete. I think having more long-term clients allows you to get to know a brand really well, and not to mention it gives you a good base for your monthly income so that you at least know you can pay your rent, buy groceries, etc. You can also set up systems to help automate your business so that you spend more time on things that matter and less time on the smaller, administrative work. Plus, I’ve learned the power of passive income by releasing my e-book Right on Pitch. It’s a digital guide to pitching publications and brands that I created for my audience that I could sell over and over again that will generate revenue without me trading dollars for hours.

Q. What is the most challenging aspect of owning your business? Alternatively, what is the most rewarding?
A: The most challenging is definitely being a one-woman show and learning to step into different roles that I’m not necessarily comfortable in yet (such as accounting and advertising) but the most rewarding is being able to make this work and do it in New York City. I love when I get great feedback from a client or when I hear that someone was able to use my tips to get a pitch accepted in a national publication. I want to help other women in any way I can so whether it’s giving them a lunch recommendation in SoHo or actually changing the course of their career, doing what I do makes me very happy.

Q: What are some of the lessons you have learned just working with brands and putting your own touch on certain projects?
A: For my freelance copywriting projects, I’ve really been able to adapt my voice to certain brands that I work with, but when it comes to projects I work on for my own social media accounts, I always try to get the best of both words so that the brand is getting what they ask for but I’m not compromising my creativity or point of view. Brands are starting to understand more and more that if they’re hiring an influencer to do work, they’re hiring them because of their aesthetic and distinct voice. If they wanted to create a traditional advertisement, they could hire an ad agency. My most successful branded content collaborations have definitely been the ones where brands have really let me take control of the assignment and trust me to create what I think my audience wants to see.  

Q: If you could share any exciting things coming up for the rest of the year. 
A: After launching Right on Pitch, I’ve been inspired to continue to create materials and products that can help others fine-tune their skills and get paid for their work. I’m going to be launching a separate career newsletter in addition to my weekly blog newsletter and I’m in the early planning stages for an online course! I’m so excited to continue to grow and scale my business in 2019 and beyond.

You can keep up with Austen by visiting Keep Calm and Chiffon or following her on Instagram @austentosone

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