All Things Entrepreneurship & Freelancing with Austen Tosone

In kicking off 2020, I really sat down to think about what I wanted more of on Blondes & bagels and what I wanted less of. One thing became incredibly clear to me…

I am not the expert. I’m really not an expert at much of anything. 

What I am is insatiably curious. I also really value connection and collaboration.

I knew I wanted to add more collaborators, contributors, and conduct more interviews here on B&B. Honestly I want B&B to be less me, and more for you – full of content that is valuable and useful to YOU. The readers. I want you to find answers and inspiration in all the content here – and I want to bring on the experts to do it.

There are so many things I know ya’ll want to know – from busting beauty myths to tapping into the wisdom of other badass women.

Which is exactly what brings us here today – one powerhouse of a woman that I’ve personally been following for years at this point:

Austen Tosone.

Austen is the content creator behind Keep Calm and Chiffon – both a blog and a YouTube channel. Austen spent years as a magazine editor, has flourished as a freelancer and entrepreneur, and now as a Beauty Content Director at Jumprope.

Austen is truly the expert at all things content creation, blogging, freelancing, entrepreneurship – and honestly navigating the waters that come with it all.

I shot over some burning questions I had for Austen and am super excited to have her on B&B to dig into, well, everything.

Former magazine editor, current blogger, Youtuber, and entrepreneur Austen Tosone dishes on all things digital marketing, owning your own business, and what it takes to work for yourself.

Tell B&B readers a little about yourself – what’s your Austen elevator pitch?

I’m Austen Tosone and I’m a content creator and fashion/beauty writer based in New York City. I’m the beauty content director at Jumprope, an app for creating and sharing how-to videos. I’ve been creating digital content for over seven years and my goal is to help people create better and get paid for their work. 

How did you get started in writing? How did you end up in the magazine industry?

I loved writing, and more broadly storytelling, as a kid. My mom was a magazine editor so I grew up in a house full of magazines and we’d make trips to our local Barnes & Noble once a month to stock up on new issues of everything from Glamour to CosmoGIRL! I did a lot of theater growing up and originally thought I’d pursue acting but I ended up transferring colleges to attend Barnard so I could be in the thick of the fashion and publishing industries in New York.

I interned at four magazines throughout college in both the print and digital departments and when I graduated I was hired on at Nylon as an assistant editor for print. It was absolutely my dream job and I couldn’t get over the fact that I actually worked there since I had grown up thinking it was the coolest of cool magazines. One of the reasons I actually started my blog in 2012 was because I wanted to practice writing and I even submitted a Keep Calm and Chiffon blog post as one of my writing samples when I was first applying to intern at Nylon.

You’ve been incredibly open about being laid off during a really tough time for the magazine industry. There is a lot of fear out there about being laid off, leaving that more corporate security and branching out on your own. Can you tell me how you processed the news? Was it an instant motivator or was there fear to overcome?

When Nylon folded it was honestly heartbreaking. I was saddened both by the fact that one of my favorite magazines would no longer be in print and also that I lost a job I loved. I wanted to take a week to just lay in bed and process but since I was laid off during fashion week I gave myself one day to cry and be sad and then I got right back out there attending shows and networking. It was really hard but I was glad that I did that because I was only out of work for a month before I started a new job at Interview magazine.

When Interview folded eight months later, I handled the news much better, but that was because I had seen it coming. That was in May 2018 and the day after we folded I went to a coffee shop and started pitching editors who I was friends with at other publications, created a summer schedule for my blog content, and planned how I could start uploading two YouTube videos a week. I was still looking for other full-time work but I figured that one silver lining of getting laid off was that this was my chance to test-drive freelancing and see if it was something I wanted to explore.

How did you come to the decision to freelance for a bit instead of immediately jumping back into a more corporate role?

Part of it was because I had genuinely always been curious about entrepreneurship and doing my own thing and the other part of it was that roles that were available in fashion and beauty publishing were few and far between and almost all of them paid less (like, way less) than I was hoping to make considering the experience I had. I figured if I could at least match my salary from Interview, it’d be worth it to stay out on my own for the flexibility and freedom to take on projects that I was truly passionate about.

This meant I had to step up my pitching game and strategy for blog collaborations and juggle lots of freelance articles and deadlines all at once. I’d say it took me about six months to really find a flow of constant work and feel financially comfortable. 

Former magazine editor, current blogger, Youtuber, and entrepreneur Austen Tosone dishes on all things digital marketing, owning your own business, and what it takes to work for yourself.

How the heck did you get started freelancing? There are a lot of women out there that would love to start freelancing or blogging, but just don’t even know where or how to start.

I completely understand this! Since I no longer had a full-time job as a safety net, it was really a sink or swim moment for me. While I think that some people need a more dramatic shift or a push to really go after what they’re passionate about, I’d advise anyone out there who is thinking about freelancing or blogging full-time to really picture what life would be like if you were your own boss. Try taking a personal day off of work and act out what you would do if you were self-employed. Think ahead and find out how much your paycheck to set aside for taxes (probably 20-25%), what you’ll do for health insurance, and where you can go to work if your apartment or home isn’t somewhere you can work from.

If you think you might like to quit someday, start building relationships now with potential freelance clients so that the day you quit you already have connections who might be interested in the services (content creation, writing, etc.) you have to offer, or better yet create a passive revenue stream for yourself like a digital product to start making money without trading dollars for hours. 

Without invading your privacy too much, do you have any income reports you can share from your time freelancing? Did you diversify or was most of your income from a specific part of your business?

So glad you asked! I have this blog post where I talk about all the ways I was making money as a full-time freelancer where I share percentages so you can see that some months one source of income was more profitable than another, which is why I highly recommend diversifying your income.

I also just posted a YouTube video talking about my blogging income from 2019 since this was the first year I made five figures blogging. My blogging income was one third of my total income for 2019 and I break down what percentage came from sponsorships, digital products, affiliates, and ad revenue as well as which platforms were most profitable. 

What “type” of personality do you think is necessary in order to freelance or be a solopreneur? Are there traits you think make or break someone in surviving on their own?

I actually think lots of different personality types can work well in the world of freelancing. I was a freelancer who was up at 7 am every day but I know for most people the benefit is creating your own schedule and adding flexibility to start your day later.

I think that the trait that was most important for me as a freelancer was organization. I was solely responsible for meeting all of my deadlines, tracking payments and business expenses, and attending important events and meetings and finding a system that worked for me so I wasn’t overlooking an email or double-booking myself was something at the top of my priority list. I think lots of freelancers probably exist in some kind of organized chaos but honestly it’s whatever works for you! When you’re freelance you always feel like there’s something more you could be doing for your business so being super passionate about your work is helpful for all the hours you’ll end up putting into your business, especially at the beginning. 

Congrats on your new role! Tell us about it.

Thank you! I am the beauty content director at Jumprope, an app for creating and sharing how-to videos. Jumprope is empowering creators to make high-quality video content from their bathrooms, kitchens, and garages by simplifying the production process with step-by-step editing. On Jumprope you create once and share everywhere so once you make a video in the app it will generate exports that you can share to IGTV, Instagram stories, your feed, YouTube, your blog, etc. so there’s no extra editing, cropping, or re-sizing on your end.

This was literally a life-changing discovery for me as a content creator and I feel lucky to be part of the team shaping what the app looks like. I oversee all of the beauty content on the app and I act as a community manager helping onboard new users and help them create great content on the app as well as a liaison between brands and media companies who may be interested in utilizing the platform for their own websites and social media channels. 

Former magazine editor, current blogger, Youtuber, and entrepreneur Austen Tosone dishes on all things digital marketing, owning your own business, and what it takes to work for yourself.

What made you decide to join a company vs continue to work for yourself?

As much as I loved life as a freelancer, I did fall into self-employment without much of a plan in place. It wasn’t as though I had left my job to start my own thing, so because of that I wasn’t able to put in place systems that would have helped me freelance in a sustainable way so that’s something that I always had in the back of my mind.

I was obsessed with creating my own schedule and choosing assignments I was really passionate about, so I knew that if I were to ever go work for another company it would have to be a pretty exceptional one that I was genuinely excited about and Jumprope ended up being the perfect fit. There’s a lot of variety in my days so sometimes I’m in meetings with brands and sometimes I’m helping our creators make their first video. I feel like in this role I’m able to flex a lot of different creative muscles.

What are/were the biggest challenges of working for yourself?

The fact that often you are solely responsible for all of the aspects for your business—you’re the accounting department, the marketing team, the HR department, and so on. If you can automate any of this with a software for invoicing or hire a VA to help with areas you struggle with it can make a world of difference. Also self-employment taxes and figuring out health insurance. 

What are/were the biggest rewards of working for yourself?

A truly overwhelming sense of pride and self-confidence when you’re successful. When you land a new client you can celebrate knowing that they want to work with you because of what you’ve built and that’s an amazing feeling. 

Is there anything you wish someone had told you before working for yourself?

Set aside at least 20% of your income for taxes. Always have a contract. You have to be both a good boss and a good employee. Hustle doesn’t equal success. Know your worth and charge accordingly. 

What’s the one piece of advice you’d give to someone who is looking to take the leap into working for themselves?

I would try to have at least 3-6 months worth of money saved up for you to live comfortably even if you didn’t make a single cent. It will give you peace of mind and freedom to fail a bit in the beginning.

Kelsey here again! Austen is seriously a gem – one of the “real ones” if you know what I mean. You can find Austen on all the below channels.







Photography by Victoria Saperstein

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