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Making the Leap From Full-Time to Freelance


Summer is knocking on your front door, begging you for attention. Living in New England, where summer never lasts long enough, it’s hard for me to say no. But with a full-time job and my freelancing work, saying no means procrastinating. It’s hard to enjoy yourself in the summer sun when you know there is a heap of work waiting for you.

I have recently told my boss that I will be going from full-time to part-time starting in October. It was a hard decision but one that, ultimately, I had to make if I wanted to stay sane.

It’s a risk—leaving your full-time job for freelancing. But this is a risk I was comfortable taking. I had two big reasons for deciding to make the leap: I am now the co-owner/publisher of a twice-annual publication and my husband and I are expecting our first child this summer. Cutting back my hours at my full-time job just made sense for us.

I started wondering how other people came to the conclusion that it was time to back out of their full-time jobs and focus on their freelance careers or small businesses. I found two women who have made the switch and thought I would share their stories. Perhaps they’ll inspire you to think about taking the leap.

Hailey Tash

Hailey Tash was asked by a friend of a friend to take some engagement photos of her and her fiancé in November 2010. Photography had been a hobby and passion of Tash’s for years, but up until that point she only took photos on the weekends of her friends, family, and nature. She had no idea that accepting this portrait job would change her life.

“I started a Facebook fan page and started posting some of the stuff I had been shooting on the weekends, along with those first engagement photos,” she says. One of her mother’s friends saw her page and hired her to take photos of a wedding, even though she knew Tash had never photographed one before.

Through word of mouth, Tash started picking up more wedding and engagement portrait work. She started a website and started building a portfolio.

During this time, Tash was working 30 as a behavioral health professional. “I longed to do photography full-time, but I was in a panic,” she says. “I graduated college in August 2011 and knew that I’d have student loans soon.” Along with all her other bills like her car payment and rent, Tash was planning her own wedding. “I had a lot of expenses, and while my business was growing, I knew it couldn’t support me.”

So she stayed at her job. “It was incredibly tough,” she says. “I’d work most of the day and then stay up late editing photos. I took longer than I should, which wasn’t fair to my clients.” When she started booking weddings for the 2013 summer season, as well as engagement sessions and senior portraits, Tash saw a light at the end of the tunnel. “I followed an international wedding photographer’s advice on how to keep your prices competitive based on your number of bookings, and eventually raised my prices enough to survive.”

When her boss asked her to increase her hours for the summer, she knew there was no possible way she could work as a behavioral health professional and handle all her photography work. “I knew those hours at home working on marketing and answering emails would benefit my business and help me grow—so I took the jump,” Tash says. “I knew if I didn’t, I would just keep waiting and waiting and it would never seem like the right time.”

This was last month, and Tash is now working full-time at her business, Hailey Tash Photography.

Courtney Balestier

Courtney Balestier has been a full-time freelancer for just over a year, hopping on the freelance bandwagon in April 2011.

“I had been on the editor track for about five years and had always wanted to eventually freelance full time and focus on writing,” she says.

Soon after graduating with her master’s in journalism, Balestier took a full-time job at Every Day with Rachael Ray magazine and soon realized that a full-time gig usually meant leaving the best writing assignments to someone else.

“I started to get frustrated assigning out fun stories that I wanted to do myself. It was still quite early in my career, I hadn’t risen far enough up the ranks to get invested in a high-stakes editorship, and I wasn’t making so much that the temporary hit in income would affect my lifestyle.”

Balestier still writes regularly for Every Day with Rachael Ray and is still on the books part-time while they make some new hiring decisions. She’s 100% happy with her decision and can’t imagine her life any other way. “Making the leap, cheesy though that expression is, is the biggest mental hurdle to get over,” she says. “After that, it comes together. Of course you have to work hard to make it come together, but it’s the most satisfying work.”

For Tash, it was the desire to open her own business and follow her passion. For Balestier, it was the desire to write the kinds of stories she was interested in writing. For me, it’s a new business and a new baby. What are the reasons for you to ditch the full-time job and go freelance?

Photo credit: Some rights reserved by xilius.




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