Diana Kelly Levey

How I Turned My Freelance Side Hustle into a Full-Time Career

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December 16, 2019

This is a guest post from freelancer Jenn Sinrich. Read more freelance writer guest posts.


Jenn Sinrich is an experienced writer, digital and social editor and content strategist in Boston, Massachusetts. She’s written for several publications including
SELF, Women’s Health, Martha Stewart Weddings, Reader’s Digest, PureWow, and many more. She covers various topics, from health and fitness to love and sex. After a decade-long career in New York City working in the magazine industry and at a myriad of digital publications, Sinrich returned to her hometown just north of Boston to pursue a freelancing full-time. Check out her portfolio and follow her on Instagram.

Advice On Turning Side Hustle Into a Full-Time Career


1. How did you get started freelancing?

I started freelancing right out of college. In fact, I was still in college when I started freelancing for money and used my internship connections to get work. I stopped freelancing on the side once I started my first job so that I could focus solely on my work, however, I picked it back up a few years later when I felt like I could better balance my bandwidth. I started freelancing truly out of passion for different topics than I was covering in my day job. I was working in the parenting and pregnancy sphere as an early 20-something. I wanted to write about the things I was experiencing in my day-to-day in the areas of beauty, love, relationships and more. Here’s how to start a side hustle while working full time.


2. How do some of the freelance rates you earned while starting out compare to now?

Freelance rates varied greatly then and still do today. What has changed drastically is my willingness to accept a low-paying gig. Now I have firm rates and do not waiver on them. When I first started out as a freelance writer, I was willing to write for any publication that was willing to pay me just so I could gain the experience even I knew I needed to demand more money. 


3. When did you determine that you wanted to freelance full time and how did the idea that come about?

I was in a job I wasn’t happy with—it was in the marketing industry. I decided to try freelancing as a side hustle out but it ended up fueling a desire in me to run home and let my creative spirit run wild.


4. How did you transition from freelancing on the side to doing this full time?

I started amping up my time spent freelancing on the side until I started pulling in enough money to support myself solely on that income. That’s when it dawned on me that I could really do this thing for a living. It took about a year of solid freelancing on the side to build enough income so that I could pay my bills (rent included) and actually save each month.  I decided to quit that job I wasn’t happy in almost three years ago and it was the best decision I’ve ever made. 


5. What are your favorite parts of being a full-time freelancer

You have so much more creative freedom and independence as a freelancer. I loved the mentorship I got from working under an editor, but it made it so I didn’t have the final say in what I worked on or what I wrote. I wanted total creative freedom to write what I wanted to write and when I wanted to write it!


6. What are the most challenging parts of freelancing full time?

You never get “time off” when you are a freelancer. In this business, you can try your best to arrange your deadlines so that you have days off, but it’s almost impossible to travel for a full week without checking your email and staying in constant contact with your editors who are trying to reach you. That can put pressure on your lifestyle and outside relationships too. (Learn how to side hustle without losing your mind.)


7. What would you advise others who are freelancing on the side and want to make the leap to full-time freelancing from home?

You have to be willing to work really, really hard to set yourself up. It will get easier, but it takes a lot of hard work. Stick with it and you will see the fruits of your labor pay off eventually.


8. What advice would you share with freelancers who plan to work from home that you think is important to your success? 

Your ability to do this weighs heavily on your personality and work style. I love working from home and am way more productive as a freelancer than when I work in an office environment or at a cafe. I’ve tried working at Starbucks and all I do is weigh whether or not I can get one more article in before I want to go home. 


9. Is there anything else that you think has been the key to your success as a freelancer and making this work?


Network, network, network. Do this with other writers, journalists, publicists, you name it. Be open to learning as much as you can from others, whether they’re doing something right or wrong. 

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