Playing the Freelancing Long Game

To many, freelance writing sounds like a fast, easy way to make good money. (Admittedly, “good money” looks different for everyone). Unfortunately, many would-be freelancers find out quickly that it’s hard to make “good money” in a “fast, easy way”. This realization often causes frustration and disappointment.

Sure, freelancing for a local newspaper or doing a few articles here and there for online job sites is a great way to earn extra cash as a side gig. For a real, sustainable career, think of freelancing as a marathon, not a sprint.  It’s very much a long game.

Veteran freelancers still remember the thrill of those first few acceptances from editors. Each one validates your choice to go the freelancing route. Never take those acceptances for granted. For most of us, there are more “This idea isn’t quite what we’re looking for” or “We’re not in need of writers right now” kind of responses than “I love this idea—let’s work together” or “Yes, we are looking to add to our roster of writers.”

It just doesn’t work that way. It helps to form a thick skin and not take each rejection personally.

Like any other relationship, it takes time to connect with editors. I’ve been fortunate to develop strong working relationships with several over the years, but it’s taken a lot of legwork. I’ve researched more sites and studied more mastheads than I care to think about.

As I’ve explained in previous posts, LOIs have been an effective way for me to start conversations with editors. Follow up emails have been the single most effective way I’ve landed work. Being a reliable writer with strong self-editing skills has helped me continue landing work, often for the very same group of editors, for years.

But it takes work. It takes persistence. And it takes a willingness to cultivate those relationships.

It can take years to get an editor to say yes. I’ve had it happen. Here are just two examples:

·         Scenario #1: A trade magazine. The trades have been good to me, and I didn’t expect this one to be any different. It was. I found the editor’s name, sent my usual LOI, and waited. And waited. I sent a follow up. I waited some more. He finally responded but didn’t have any assignments right then. He might have something in the new year…a few issues away. I waited some more. I responded professionally and enthusiastically each time. I let him know I was available for whatever writing assignments he needed covered (my standard response). Finally, finally, something came up. I wrote product round-ups for the publication for about a year.  It turned out to not be a good fit for the long term. As other steady clients have gone in different directions in the past year, I looked up that publication once again. They have a new editor, so I reached out and started the relationship building process over again. We’re talking.

·         Scenario #2: A university publication. I’ve been fortunate to write for nearly a dozen alumni magazines for colleges and universities of various sizes. These publications have been tougher to break into, mainly because most of the writing work is done in-house.  I send a round of emails out to higher ed mar comm folks every so often. One local-ish university has been especially difficult to reach, but I was determined. First, I went down a rabbit hole of contacts. I tried the usual folks—mar comm, development, etc.—but no luck. With nothing left to lose, I reached out to the communications director for one of the university’s colleges (many larger schools have smaller “colleges”—College of Education, College of Business, etc.). Finally, I received a positive response—he was revamping the website and needed writers for several profiles. I just wrapped up my first piece a few weeks ago. I’ve reached out to several different marketing and content folks at the school over the last two or three years.

I never stop sending LOIs, even if I receive a positive response. Any assignment might be your last.  It’s unwise to rely on one or two potential clients, and always, always follow up.  I recommend having several irons in the fire at any given time, as it were. Some of my regular, bread-and-butter clients have taken their work in house or changed direction in other ways, but I’ve built enough of a network that I’ve been able to stay afloat through follow ups and referrals from other writers.

It’s a tough time to try breaking into freelancing, but it’s not impossible. With persistence, a little creative thinking, and a willingness to network, you can set yourself up for a satisfying long-term writing career.

Writers, how have you set yourself up for the “long game” of freelancing? What advice or experience would you add?