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The Writer’s Mindset: Inside the Head of a Successful Freelancer
by Kelly James-Enger

Picture a fulltime freelancer. What do you imagine? A person who sits around in pajamas, stopping now and then to write when the muse hits? Someone who’s more worried about their artistic vision than making a living? Someone who’s committed to writing fulltime even if it means surviving on peanut butter sandwiches?

That’s the common stereotype, but I’ve found that it’s unfair—and untrue. The fact is that successful freelancers are likely to be organized, professional, and deadline-oriented. Surprised? Most of the successful freelancers I know—and I’ve interviewed dozens of them—have a number of personality characteristics in common, and I don’t think that’s a coincidence. In fact, I think there’s a certain personality type that thrives on freelancing. Do you have what it takes?


Many people think that freelancing fulltime is a great career because you can set your own hours and work when you want to. While that’s true, it also means you don’t have a boss standing over you to make sure you’ll get your work done.

The reality is that it takes a certain amount of drive to freelance successfully. If you miss deadlines at your job, when you have a boss to answer to, how will you force yourself to work when it’s gorgeous out and you feel like taking a long afternoon off to golf? Successful freelancers are motivated not only by external sources like deadlines, but from within.


It’s great to have a plan when you start out. But you have to be willing to change that plan if conditions dictate. For example, when I started freelancing, I only pitched ideas that interested me. But I quickly realized that if I was seriously about making money, I’d have to accept that not every assignment I took would thrill me.

Sometimes I do write about subjects of personal importance or interest, but much of the time, I’m writing about subjects I find somewhat…dry. That’s part of the gig when you write fulltime. I’m not saying you must take on work that you detest. But if you’re going to make a living as a freelancer, you need to accept that plenty of what you write won’t excite you the way your novel or screenplay or personal essay may.


Forget the writer toiling away alone in his garret. To succeed in this business, you need to be able to build relationships with your clients. That means having some degree of people skills.

Sure, if you’re dripping with talent, you can get away with some prima donna behavior. But most editors and clients want to work with writers they like. I’m not saying you have to be best friends with the people you work for, but it doesn’t hurt to have a friendly relationship with the people who write your checks.


Want to be a successful freelancer? Then act like it. Confidence means that you’re secure in your abilities. It means that you’re willing to negotiate for more money when you know you deserve it. Confidence isn’t about having a big ego (although that’s certainly OK!) Confidence is appreciating your unique set of skills and what you bring to any writing project—and letting clients see that.

Not feeling confident? Fake it. Believe me, I have bad days where I worry about making enough money or that my writing won’t measure up. But I don’t share those feelings with potential customers! To the outside world, I always act as though I believe in myself and my abilities—and guess what? People buy it.


I’ll tell you—you’re going to face some hardships as a freelancer. Story ideas you pitch will be rejected. You’ll contact potential clients who will shoot you down. A story you’re slaved over will be killed. Bad things happen to freelancers all the time. But the ones who succeed simply don’t get derailed by failures or mistakes. They learn from them and move on.

Several years ago, I decided I want to branch into writing nonfiction books. I’d been a magazine journalist before, and spent three months toiling over my first book proposal. It was a great idea with a built-in audience with few competing titles. I was certain it would sell.

Guess what? It didn’t. All that work—down the tubes. I could have given up on my book writing career right then. Instead, I moved on to the next project and pitched another book idea—which sold. I’m working on my fourth nonfiction book now.

Freelancing has ups and downs like any business. Your ability to tough out the rough times and keep going will help ensure your success as a fulltime writer.

© Copyright 2004, Kelly James-Enger

Kelly James-Enger has authored more than a dozen books, including Writer for Hire: 101 Secrets to Freelance Success (Writers Digest, 2012) and Goodbye Byline, Hello Big Bucks: The Writers Guide to Making Money Ghostwriting and Coauthoring Books (CreateSpace, 2010). Check out her blog, Dollars and Deadlines, for practical advice about how you can make more money in less time as a nonfiction freelance writer.

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