How I Redefined Career Success as a Freelancer

Stepping away from an expected career trajectory hasn’t always been easy.

“It would be a full-time job in the office.”

These were the words I had been waiting years to hear, and yet they were filling me with a slight sense of panic, not excitement. I graduated from journalism school in 2010, and newspaper jobs were coveted. They were the gold standard of success in a dying industry. Yet, I knew exactly one person in my prestigious, big-city journalism program who worked in a newspaper office.

In the two years since graduation, I had started freelancing, supplementing my growing writing business with nannying. Although the situation was very different from what I imaged when I started college, I was fulfilled, enjoying working on an array of writing projects while maintaining control over my hours and interests.

Now, however, that old expectation of success had come back full circle. I was sitting across from an editor for whom I had freelanced regularly, and she was offering me what had once been my dream job.

“I’m going to have to think about it,” I said, quickly adding, “but it sounds great.”

The unfortunate truth, however, was that it didn’t. I would be taking a pay cut working at the newspaper, even though I would be working more hours. I would lose the flexibility to travel (one of my great passions), as well as simple pleasures like working outside on a sunny day.

Yet the pull of expectation was too strong to resist. I told myself that the job would be a learning experience, but really I only accepted the job because I felt I should accept it. I thought of the generations of women who had fought to have their voices heard, and I couldn’t pass up the opportunity to do just that.

I did learn a lot at that job: about office politics, the editorial process, and producing publications on a shoestring budget. However, my biggest lesson was much more personal. I remember looking at my editor, whom I admired greatly, and thinking, “I never want her job.” I realized that I valued flexibility and self-direction over a full-time salary and a leadership position. When I had my first child a year later, I quit in order to go full-time freelance. And I’ve never looked back.

Stepping away from an expected career trajectory hasn’t been easy, especially for someone who was always the teacher’s pet and known for making the “right” decision. But I’ve learned that the right decision is whatever works best for my family and me. Some of my most tightly held values are independence, self-determination, and family. Being self-employed as a full-time freelancer is the career option that aligns with those values most fully: I am able to spend time with my child, make enough money to support myself, and maintain a flexible schedule that accommodates impromptu summer trips to the lake.

Although I’m now fully confident in my career choice, I’ve had to accept that many people don’t understand it. Friends and family members don’t realize that I contribute as much to our household financially as my husband does with his traditional job. People often ask me to do something on a whim during the week, and I have to remind them that, although I have flexibility, I also have deadlines, clients, and a real business.

Of course, I don’t need other people’s validation, but sometimes it is nice to have. In a traditional career, family and friends would help you celebrate milestones like promotions and raises. My career doesn’t fit those molds, but that doesn’t mean I can’t celebrate my successes.

Last year I surpassed my income goal, and I celebrated that with my parents, in-laws, and siblings. I used to shy away from bragging about my success. But I’ve realized that my career is just as legitimate as anyone else’s, and if I want that to be recognized by the people I love, sometimes I have to help them understand. I also want to show my siblings — especially my younger sister who recently became a mother — that we are empowered to choose whatever career we want. Yes, women are now able to succeed at every level of business, but we’ve also fought for the right to step outside social expectations and plot our own course.

Last week, I was once again offered a full-time newspaper job. I still hesitated, but not for nearly as long as I did five years ago. Then I said confidently, “I appreciate that you thought of me, but that doesn’t align with my current career goals.”

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2 Responses to “How I Redefined Career Success as a Freelancer”

  1. Sarah

    Is there a way to be self-employed and afford health coverage that will cover my type 1 diabetes that is a reasonable cost for the insurance? I feel like I have always been tied to working for big corporations because of my chronic illness.

  2. Dana Leavy-Detrick

    I definitely have been in Kelly’s place where you’re dealing with people’s (particularly close to you) perspectives on what it means to be fully self-employed and successful, especially as a woman. Part of the reason I love working for myself is that I highly value that freedom to adjust my [sometimes inflexible] schedule, choose the projects I want to work on, and build something I’m proud of – but often, others see that as perpetual summer Fridays (every day), flexible calendars, and no obligations. This article is a good reminder to shut out the noise and focus on building a career and life that fits your rhythm, and the needs of your family.