Redefining Success: Freelancing on the Path to an Alternate Destination

I am a writer with big dreams. A little over a year ago, I quit my full-time job to become a full-time freelancer. I pick up a few editing and marketing jobs on contract to help pay the bills, but I’m pushing hard after the writing career I’ve always dreamed of.

Chasing a big dream for me, however, means struggling with a mindset of “never good enough.” If I am doing the writing I want to do and making the money I need to make, why am I still going after more?

In her book Rumors of Water, author, publisher, and entrepreneur L.L. Barkat talks a lot about the importance of thinking small as writers. In one chapter called, “Can You Find a Small Audience,” she talks about writers who seek too large an audience too early in their careers.

“I’ve heard it said that most successful writers put in about fifteen years of small-audience writing before they begin to work with larger audiences,” she writes. “There are exceptions of course, but if every writer with a publishing dream thinks he is the exception, the math doesn’t work out.”

Then in a later chapter, she offers more math that often doesn’t work out for the writer who is dreaming big: 80 percent of titles tracked by Nielsen Bookscan sold fewer than 99 copies and the average book in America sells only 500 copies. How does that add up to success?

Maybe by redefining success. A few years ago, Kevin Kelly first wrote about the concept of 1,000 true fans. He said if a painter, writer, musician–anyone working in the arts–has 1,000 true fans (someone who will purchase anything and everything you produce), he could make a living.

The idea may not have been entirely original, and in fact, he said many artists he knew were already following the principle without calling it by any name. But here’s his point: “You don’t need a hit to survive. You don’t need to aim for the short head of best-sellerdom to escape the long tail. There is a place in the middle, that is not very far away from the tail, where you can at least make a living. That mid-way haven is called 1,000 True Fans. It is an alternate destination for an artist to aim for.”

As a freelance writer and editor who is exhausted by the crowded, high-speed superhighway of “never-good-enough,” I am on the lookout for the path to that alternate destination. It may not exactly be “1,000 True Fans” or some other cleverly labeled strategy, but it will have the following characteristics:

1.)   Allows me opportunities to write. There will always be more, better, and bigger writing assignments to go for. Always. And I don’t think there’s anything wrong with occasionally taking a risk and attempting a big sell. But if I’m already doing the kind of writing I enjoy on a regular basis, that’s a gift I don’t want to take for granted. The opportunity to write is why I quit my job in the first place.

2.)   Provides a real audience. My potential audience will always be larger than my actual audience. But those engaged readers who already have found their way to me through my writing? I want to hang on to them. Having an audience means getting feedback, having conversations, and getting to know a lot of great people. Having a real audience (not just a potential one) is an important element of being a successful writer.

3.)   Supports the rest of my life. I may have spent a lot of time working on my identity as a writer, but it’s not the entirety of who I am. I am married; I have stepchildren; my parents live nearby; I attend a local church; I tutor at the library. A successful writing career is not just one that allows me to make a living, but it’s one that lets me have a life. I can always find more assignments or take on additional clients or pitch more books with the hope of making more money and achieving bigger success. But I have only so many hours in a day and so many years with my family. Having a writing life that gives me time to work and time to play and rest is crucial to my long-term success.

4.)   Gives me satisfying work. Every week, I get to work in my primary genre–essay writing. Just because I also write newsletter articles and edit other peoples’ books doesn’t take away from the enjoyment I have in doing that creative non-fiction work. And having the time to do my own writing gives me the motivation to help others with their work. Especially when most of the clients and projects I take on are ones that I really believe in. Doing the work I enjoy is a key element to my success. If I enjoy the work I am doing, I am less likely to feel the burden of “never-good-enough.”

5.)   Allows me to make clients, editors, and readers happy. Chasing after dreams of big-time success for me often means trying to do too many things at once. Then, I get careless with the work I already have, and my chances at even small success are sacrificed. Treating every essay, every book, every blog post, every newsletter article as if it is the most important one helps me keep clients, editors, and readers happy. And that’s a big part of my success as a writer: making positive connections with those who interact with my work.

There’s nothing wrong with big dreams and big-time success. For some people, those things happen overnight. For others of us, they never happen. But that doesn’t mean we can’t find another path toward a satisfying writing career, one where meeting our goals looks a little different than we once imagined. That’s the path I want to walk on.

Originally published at the Grubstreet Writes Blog on July 29, 2015.

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Charity Singleton Craig

Charity Singleton Craig is a writer, author, and speaker, helping readers grow in their faith and experience true hope in the middle of life’s joys and sorrows. She is the author of My Year in Words: what I learned from choosing one word a week for one year and coauthor of On Being a Writer: 12 Simple Habits for a Writing Life That Lasts.