Typewriter at the flea market

How Not to Succeed As a Freelance Writer

I’ve been freelancing on and off for more than 15 years. While I’ve been lucky to land some decent-paying projects with a few well-known publishers and online outlets, I’ve always wondered whether there is a secret formula to getting more work.

In fact, there is a secret formula to getting more freelance assignments, just as there is a secret formula to getting a fitter body: do more, work more. In both cases that’s easier said than done. I know what I should be doing but often I lack the motivation and stamina to get to the next level.

This is why I’ve been thinking about how to approach this issue from the opposite direction. I am not sure how one succeeds as a freelance writer — success is subjective and hard to define — but I do know what it takes not to succeed.

With the hindsight of 15 years, here are the things I should’ve done to get further as a writer. Consider it anti-advice from someone who knows better.

Don’t Pitch

Freelancing without pitching can be done. This has been my M.O. almost exclusively. For years, I have waited for projects to come to me rather than pursuing projects that I want to do. Part of this has been a lack of planning, which wasn’t a problem during the years I was freelancing for the fun of it, for pocket change. But the main reason I haven’t pitched is out of fear—fear of time spent working on a query as well as fear of rejection of that same query. “Why spend so much time working on something that may not get picked up?” I thought. My aversion to pitching early on in my career, when I didn’t have kids and had so much more time, has meant that I am under-practiced now, when I am trying to freelance full-time and need to be more aggressive in order to get more paying work.

Pitching is one of the most important elements to freelance success. Learning how to do it is essential. Try these resources:

Don’t Network

Freelance writing may seem like a solitary affair, but it is also like any other job or perk: who you know is as important as what you know. If an editor knows you, he is more likely to take a chance on you than someone he doesn’t know. Likewise, the more people you know, the more likely you will be able to find and reach an editor who may want to publish your work.

This is Freelancing 101. But it is another facet of freelancing that is easier said than done, at least for me.

I recently had a conversation with a friend who graciously offered me query advice and an editor contact, even though I already knew another editor at the publication fairly well. “I’m not sure I shoud try him since I know him,” I said, knowing that this thinking was counter intuitive as well as counter productive. “Yeah, I get it,” she replied. “You don’t want to feel like you’re using, or taking advantage. But I say pitch to whoever you’ll have the most success with!”

Pitching and networking go hand-in-hand, so it is important to make connections. But it also important to know how to use them.

I should note here that women, more than men, are less inclined to use friendly connections for business pursuits.

Don’t Have A Point of View

So much writing these days is done for the internet and the internet loves debate. Having a strong, even outrageous opinion, on an issue typically brings in readers and sharers, especially those who have the exact opposite opinion as you. That results in increased page views which results in pats on the head from your editor, name recognition, and, possibly, subsequent assignments.

A few years ago, I wrote a piece called Why I Hate the Amazing Race. While I feel that my argument was measured and solid, I still cringe when I read the title. I don’t really hate the Amazing Race; I just kinda sorta don’t like it. But “Why I Kinda Sorta Don’t Like The Amazing Race” isn’t the kind of title that brings in readers.

I don’t hate many things, but I do hate the current system of Internet metrics that rewards outrage over nuance. And I realize that there are plenty of stellar sites that do not (or rarely) peddle in this kind of clickbait. But having an opinion, a point-of-view–convictions–will help guide you as you look for stories and write. This applies more to essayists and travel writers, for example, than it does to those who consider themselves objective journalists. However, NYU journalism professor Jay Rosen argues that even journalists need a point of view: “Intellectual honesty is a more reliable basis for trust than a ritualized objectivity. A clear voice is more valuable than a nonpartisan veneer.”

Don’t Keep a Schedule

One of the best things about freelancing, making your own hours, is also one of the worst. Having an open schedule makes it easy to say, “I’ll work on that tonight while the kids are asleep” or “I can finish this over the weekend.” But just like with exercising, if you don’t make time for writing, if you try to squeeze it into the bits and pieces of time that’s left over, you either won’t get it done or you won’t get it done well. Honor your work enough to make time for it. This is definitely “do as I say, not as I do” advice because I fall into this trap a lot — both with writing and exercising — and it doesn’t feel good.

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These are just a few of the things you can do to stagnate in your career as a freelance writer. What advice (or anti-advice) do you have? I welcome your comments below.

Your Thoughts?