The freelance life, redux

10 lessons from my first year of freelancing

This month I celebrate my one-year anniversary as a full-time freelance writer. I’ve managed to more or less maintain the lifestyle—granted, it wasn’t lavish—that I had when I was employed full-time on staff. “How do I make it as a freelancer?” is far and away the most common question I get. When I first attempted to tackle it, just a few months into my freelance career, I was perhaps rightly excoriated by commenters for presuming to think I had some answers. Now that I’m a bit more seasoned, I want to take another stab at it. Here are the most important things I learned in my first year as a freelance writer:

1. Have a staff job first. One reason I’m able to be so productive as a freelance writer is that my years of editing experience trained me to write a thesis graf quickly, to pitch and outline big features effectively, to revise, and to write a draft headline before I submit a first draft. In other words, editing helped me earn a reputation as a writer who submits clean copy. It also taught me respect for the editor’s point of view, which can be a great asset. If you understand just how many assignments and writers your editor is juggling at any given time and what sort of communication she needs to do her job effectively, chances are your relationship will be a relatively smooth one.

2. Go out with a bang. Other than my editing experience, the fact that my colleagues and I were fired together was a great boon to my writing career, especially in the early months. These days, as so many journalists are pushed into the realm of freelance by taking a buyout or suffering a mass layoff, which means that other journalists are aware of your plight. When you get those friendly emails that say, “Let me know how I can help!” ask each person for personal introductions to three editors who accept freelance pitches. These are the contacts that will make your freelance career feasible.

3. Be prepared to write. A lot. This is not to say that quantity is more important than quality, but productivity is key to making it. Every word matters. You’re gonna work really, really hard.

4. You are now the CEO of a corporation of one. Act like it. You’re not just a writer. You have to worry about things like finances, branding, and market research. Get your personal website in tip-top shape. Promote the hell out of your work on Twitter, Facebook, Tumblr, Pinterest, email, all of it. Get an accountant. Make a budget and keep your paperwork in order. Think about how all the assignments you take are adding up to a professional narrative—if editors have a clear sense of what you frequently write about, you’ll be more likely to leap to mind when they’re looking for a writer on those topics—and make both a one-year and a five-year plan for yourself.

5. If a pitch is really good, it won’t work for more than one publication. This is why cold pitching is so exhausting. The best pitches are tailored to a specific outlet and editor—ideally someone to whom you have a personal connection. A great pitch is a perfect match between the idea and the outlet, with a time hook that forces the editor to say yes or pass right away. That said, you can take some ideas and reframe or repackage them to work for a different publication. Use every reporting trip at least twice.

6. Get a column or a recurring gig. If you can’t land a weekly slot, make a serious effort to develop regular relationships with editors. Send the next pitch as soon as your previous piece has run, so it becomes a continuous cycle. This benefits both of you: Editors like regular, reliable writers whose strengths and shortcomings they know. You’ll get better editing, be able to make a more reliable budget, and probably have an easier time dealing with the accounting department about your payment. It’s because of my regular columns that I’ve spent far less time chasing down checks than I thought I would. And productivity-wise, it’s nice to be on the hook for a certain amount of work every week. On that note…

7. Love your editors. They are your lifeblood, your direct employers, your internal advocates in case that check hasn’t come. Also, they’re now your coworkers. Treat them as such. Always be gracious about edits—even if you disagree with them. Never hit “send” if you’re angry.

8. Ignore your haters. Anyone creating anything of interest or value is going to attract a few people who disagree. Separate productive critics from basic detractors. If you must pay attention, use your haters as motivators.

9. Ask for more money. You’re not an asshole for asking for more more—let’s be real, you’re not exactly Scrooge McDucking it. You’re just getting by, and your life and finances depend on you squeezing a few more dollars out of every assignment. Just ask. But also be willing to do some things—things you’re passionate about, that open up your work to new audiences and editors, that you would have written/created anyway—for little or no money. For a long time, I made pie charts for The Hairpin for free. That led to a paying gig with Los Angeles magazine, and eventually a little bit of money from The Hairpin, too. But it took awhile. Also, be unwilling to do some things, even for a lot of money. I turned down a very plum assignment from a magazine that wanted me to write something negative about women. That is not what I’m about. (See “personal brand.”)

10. Put the ‘freedom’ in freelance. Go on walks in the middle of the afternoon. Skip town and work from a friend’s porch on the other coast. If you’re not being productive in your house, get out and try a new coffee shop or the library. Set up random daytime activities—shadow a friend at his or her job, take a tour of the local power plant, whatever. All of these things can spark story ideas. Choose to work alongside your friends, or alone. Switch it up. Don’t spend all day every day hunched, Gollum-like, over your laptop. One of the best things about this job is that you aren’t tied to a newsroom.

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Ann Friedman is a magazine editor who loves the internet. She lives in Los Angeles Tags: #Realtalk