I switched from being a staffer at Entertainment Weekly (where I worked for almost ten years) to being a freelance writer in 2011. Believe it or not, I had dreamed of being specifically a freelancer since I was a little girl. I had always wanted to be a writer, and I loved the library. I spent a lot of afternoons there looking up stuff that interested me in the card catalog, then reading all I could about it. When I read books about writing, I learned the word freelance. I was 8. I thought it sounded so wonderful: Freedom! A lance! Writing! So when I was finally able to make the transition 27 years later, the move was long overdue.
I made the transition as I do most things: responsibly, and with a lot of forethought. And yet I also made lots of mistakes along the way, and found that the transition was even harder than I had expected. I hope I can share a few of the things I’ve learned so I can help others who share my love of freelancing and my aversion to avoidable mistakes.
This Ultimate Guide is for people genuinely considering going full-time, for-real with their freelance writing. Freelance writing can be a great little side gig for some pocket money, and/or a lovely hobby. But what is below will help those who want to make it their main life’s work. The first thing you need to do is realize that this is a business. When you become a freelancer, you become a CEO of a one-person company. You must start acting like it. You will have bills to collect and bills to pay and marketing to do. You must take all of these things seriously. You aren’t just some artiste for whom the rest will just fall into place. That was advice I got when I first started, and it was critical.
So. Let’s do this. This guide is organized by subject area, with some Q&A format thrown in occasionally — me answering some questions I got when I asked for them in a previous post. If you have other questions that aren’t answered here, leave them in the comments, and I’ll add them in (with answers!) when I can. Let’s start with a question, since this one is a great place to start.
Q: I’d like to know more about the transition from part time freelance work to full time writing. Like… when would a writer leap from “don’t quit your day job” to “I totally quit my day job!”? (from Chrissy Layton)
A: I’ll share my experience first, then add some thoughts based on what I know of other successful freelancers. I’m not the best with money, so I wanted to make sure I had some sort of safety net in place before making the leap from regular paycheck to … not. So my plan was to sell a nonfiction book, and I had a minimum price in mind that would allow me to quit my job. I had written one book at the time, and I had done that while holding down a full-time job, and I swore I’d never do that again. (I wanted a personal life.) But I also felt like I needed a six-figure deal, given that it would be broken up into thirds and dispersed over a year or two of payments. (When you sell a book on proposal, there are various methods of payout, but mine is fairly common: I get a third on signing, a third on manuscript acceptance, and a third on publication.) The point of all this is to say that I did get the deal I wanted, so at least I knew I’d have some five-figure checks to count on showing up at certain points. (Please see this post for a further exploration of why I could think this was a reasonable price to expect.) These would allow for a solid eight months or so of living expenses to give me a running start; during that time, I hoped I could build my business up enough that I could keep going. So far it has worked, though with a few pretty dire dips in income. We can talk about that a little later.
I do know others who make it work without book deals from major publishers. The most basic advice I usually hear from them is similar to the book deal idea, from a different angle; they like to have at least one “regular” gig. This is a client that uses them consistently, usually with some kind of commitment: say, an actual contract to pay you a certain amount per month for a certain amount of work, or a regular column. One of the most impressive freelancers I know is Jen A. Miller, who has been making it work for ten years now. Check out her website; she sometimes writes about freelancing. (She also gave me a bunch of great advice when I was still struggling.)
So, bottom line: Get some regular stuff lined up that you can count on. Or save an absolute ton of money before you make the leap.
Get experience! That’s seriously the whole game when it comes to being a published writer. You need what we call “clips,” which we call them because in the olden days we actually clipped out our little pieces and kept them in little scrapbooks and made copies of them to send out with our query letters. Now it’ll just be links to your published work in an e-mail query letter (more on that below). You need clips. Get as much work as you can when you’re starting out so that you can show it to potential clients. This usually means working for free or very cheap for smaller websites and publications. Find a website that takes submissions but doesn’t have the budget to pay writers; you come in to save the day, and you get a nice clip out of the deal. When I ran SexyFeminist.com, we often worked with inexperienced writers; we didn’t mind giving them the extra editing help, given that we had no money to pay them. This allows you to get real experience and samples of your work so you can eventually move up to the bigger places that pay better. I’m also a fan of local newspapers (or news websites), if you can find them. They’re a dying breed, but I started my career at local newspapers and got invaluable experience. Those were the worst, most stressful years of my life, but I’m glad I did it now. I haven’t been clip-less since I was 17. And if they let a 17-year-old wearing her mother’s clothes work for them, they’ll probably let you.
Q: I would like to know which websites are the best for finding freelance work. (from sahmoun2778)
A: I don’t love this method of finding freelance work, but it can do in a pinch or if you’re just starting out. The one place I’ve found work that paid decently and didn’t end up being some sketchy gig is Mediabistro. It’s worth the small membership fee to join. There’s also an amazing section called How to Pitch that I will talk a bit more about later. I did dabble with Elance, which requires that you sign up, then sends you jobs that match your skills; it seemed decent, though every time they sent me something I was swamped with higher-paying work. (I know, high-class problem. Funny how this never happened when I was desperate!) All the others I’ve tried — when I was desperate and just searching for anything to fill my bank account — didn’t pan out. That said, I haven’t tried this a lot or consistently, so if people have had good luck somewhere, feel free to let us know where in the comments.
Also, FreelanceWritersOnline has a terrific list with pros and cons for each, suggesting they’ve done some serious investigation.
You’re going to start out doing a lot of this. I want to break it down to the basics.
One way you get assignments, especially when you’re first starting out, is to pitch your ideas to editors who might want to buy them. This often serves as a kind of “audition” for writing for the publication. When you’re more experienced, you’ll still want to pitch sometimes; you might be getting more direct assignments from editors (i.e. they say, “we need someone to interview so-and-so, will you do it?”), but it’s fun to execute your own ideas sometimes. This happens with a pitch letter. Really, these days, almost universally, a pitch e-mail.
How do you make one of those? Here’s a step-by-step guide:
1. Study publications. Narrow your targets down to just a few perfect places where your pitch might be at home. Do not send out a form letter to 55 publications. They’ll notice. Aim for three to five, tops. Hone each pitch to that individual publication. Even within certain categories, every publication is different. A Glamour pitch about, say, in-vitro fertilization is different from a Cosmo pitch about IVF, which is different from a Marie Claire pitch about IVF. If you don’t see the differences, it’s not the right category for you, or you need to study more.
2. Figure out whom to contact at each of your targets. Some publications, especially smaller websites, have very thorough instructions about contributing right there on the site for anyone to see. Follow their instructions. Others, especially bigger publications, can be tougher to crack. First, I recommend sending to a real human whenever possible (as opposed to firstname.lastname@example.org or whatever). Second, if you can’t figure out the exact right editor (i.e. you have a health-related pitch and they have a person called the “health editor”), maybe just pick one who sounds nice. Seriously. It’s better to get it to the wrong human, who can send it to the right human, than to send it to a generic account no one of consequence every checks. Aim for the middle of the masthead (that page where they list the staff) if it’s a large staff. (In other words, don’t send it to the absolute top editor, who’s often more of a figurehead than a day-to-day editor, and don’t send it to an assistant. People like “senior editor” or “features editor” or “articles editor” are often good bets.)
Don’t worry, there are some great resources to help guide you through some of this. The classic is Writers’ Market, which has been around since the dawn of time in book form and is now available online as a database. Of course, you have to pay a small fee. But it is extremely comprehensive, even if its listings are fairly brief. You’ll get a little info on the publication and some kind of contact.
I absolutely love Mediabistro’s How to Pitch. I mentioned this before. You have to sign up to get this part of the site, but it’s so worth it. The listings aren’t as comprehensive as Writers’ Market — they don’t have every single publication here — but they are quite in-depth. For each publication included, Mediabistro actually interviews the editor most likely to take freelance submissions, and gleans all kinds of detailed information — what they’re looking for, what they hate, which sections are best for newcomers, what specific freelance articles they’ve accepted recently. They also usually include the pay rate and, miraculously, the e-mails for the appropriate editors.
3. Now write your pitch.
This follows a basic formula. It usually goes something like this:
LEDE PARAGRAPH: An attention-getting way into your subject, similar to what you might write as the first paragraph of the actual piece.
NUTGRAF: An overview of your story. Why should we care about this? Why now? Why is this right for this audience?
PROPOSAL PARAGRAPH: How will you execute this story? Whom will you interview? How many words do you envision? Which section do you think it’s right for?
YOU PARAGRAPH: A brief bio. Emphasize your qualifications for this particular topic, as well as your writing experience. Mention that you’re including links to your published work below. Include those after your sign-off.
SIGN OFF. INSERT CLIPS. SEND.
Here is a pitch I recently wrote that resulted in an assignment for Mental Floss. Please note that I know this editor personally, so I get a little casual toward the end — I didn’t have to send her my clips or sell her on the idea of me.
Hi Abbey —I’m a chronic Googler of almost all problems in my life, so I inevitably run into WikiHow with some frequency. (“How to Hard-Boil an Egg,” “3 Ways to Cure the Common Cold Naturally,” “How to Be Like Beyoncé” … I’ll take them all.) What has struck me, however, is that, unlike, say, “Yahoo Answers,” WikiHow is often dead-on, thorough, and helpful, even if it’s written as if explaining the world to an alien. (From How to Edit a Book, step 1: “Find something to edit. To edit a book, first you need to either write the book or get a book you want to edit.”) The How to Be Sophisticated is startlingly on-point, with advice about posture, haircuts, grooming, fashion (scarves are key), and conversation topics (museums, good wine, and travel are go-tos). I was shocked when I looked at How to Become a Writer and realized that if you did every one of the steps mentioned, you really would be in great shape (and probably wouldn’t need to take any of my or anyone else’s writing classes). Oh, and the animations, with their dreamy pastel colors, are gorgeous and distinctive. I’ve been threatening to make How to Become a Writer into a poster for my office, and there is a Twitter feed dedicated just to WikiHow art appreciation.I thought it would be fun to do something on how WikiHow works, perhaps similar to your recent piece, “19 Secrets of UPS Drivers.” WikiHow now has nearly 200,000 entries (including such gems as: How to Make a Goldfish Live for Decades and How to Break Up With Your Boyfriend If You Are in Love With Him) and is seeking more on some of the craziest topics you can imagine (How to Drill a Hole in a Glass Bottle …?). They are currently building versions in 13 languages and are read by a million readers per month. They’re still headquartered in a house in Palo Alto. And WikiHow is still entirely funded by its founder, Jack Herrick, instead of Venture Capitalists.I would love to talk to the folks at WikiHow HQ as well as some of the writers of the weirdest/most popular/best entries about why they do this, how they became “experts” in these things, how entries are policed, how the editing process works, and how the illustrations come together. This girl, for instance, has created 108 entries (How to Paint a Rock Using Toothpicks, How to Make a Monkey out of Clay …). As you can probably guess, they’re not paid, so something special is driving these folks. I could also put together a few WikiHows of my own to explore the process further.Let me know if this is something you’d be into; I’m happy to reach out to a few of them to suss out some details if you’d like.Thanks,Jennifer
Q: Besides cold queries/submissions how can a writer connect with publishers — i.e. blogs, talks, workshops, etc.? (from BajaMotoQuest)
First, I want to mention that queries can be a way of connecting. I mean, in the obvious way, sure: You ask them if you can write this story for them, and they miraculously say yes. But as I said above, I like to think of queries as more of an audition. You’re showing them you can think like their publication and write in their voice. If they like your query enough, they may invite you to pitch them again even if they have to reject that specific idea. I’ve spent years courting some magazines this way, before eventually either getting an assignment or finally landing a pitch. (Glamour, O, and Women’s Health worked for me this way.)
But you’re right to be wary of this method. It sounds magical — send off your ideas, and boom! you’re suddenly published! — because it is, in the sense that it is so rarely successful. Having personal connections to editors before pitching makes all the difference. The vast majority of my work comes from editors who used to be my coworkers at Entertainment Weekly. The second most likely source of work for me? People I mentored who are now far enough along in their careers to commission me to write for them. Personal connection is everything. Some ideas for making those connections:
1. Online networking. A lot of people are skeptical of this, but I believe in it. I’ve made several real, meaningful connections this way. You need to build it organically, though: commenting regularly on someone’s blog, sharing their posts, possibly dropping them a complimentary note via email if that seems right. You can use Facebook’s feeling of community to connect on a personal level, enough that you eventually feel you can direct-message the editor and ask about pitching. (One friend-of-a-friend and I found ourselves routinely “liking” each other’s comments, saying the same things, and laughing at the same stuff. We became “real” virtual friends. I didn’t even realize she was an editor. Then one day when I posted about looking for freelance work, she invited me to pitch her.) Same goes for Twitter: If you can become genuine buddies there, and you’ve had several exchanges, a “cold” pitch to that person is no longer cold.
2. Talks and workshops. I love this idea! I teach and give talks, and I never mind if someone figures out a way to get in touch afterwards. Again, start with a complimentary note and ask if you can join this person’s mailing list or somesuch. Follow him or her online. Then, over time, it could feel right to pitch that person.
3. Readings. This is slightly different from the talk/workshop idea, but it’s one I always mention to my students. If there are smallish literary readings in your area, go to them. Not the big blockbuster ones, like Stephen King at Barnes and Noble. More like mid-list authors at local indie bookstores and bars. Here’s why this can work, especially in a media-heavy town. (I admit, it probably works best in New York, but a Seattle or Chicago might do.) The same people are always going to readings. We are sick of them. We groan, at least inwardly, when we realize we have to go to another one. All of our friends are always having damn readings, and all the same people will be there. We are so excited if someone new shows up! We welcome this. And many of us weary souls happen to be writers, agents, and editors, because we all hang around each other. You won’t likely leave with a major assignment. But if you play your cards right and make some friends — definitely go to the party at the nearby bar afterwards! — you will come away with friends. Nice, literary friends. Nice, literary friends who can publish your work or know someone who can.
I’d like to note these all work best as long games. No one likes the person who shows up at the reading or the talk or the class with a manuscript to shove in the talker/teacher/reader’s face. We are generally paid for our services, and, no, dear total stranger, we would not like to read your manuscript unless a check is attached. If you become our genuine friends, however, we may, in the long-term, be more than happy to help you. You have to earn your way in, though. Think of ways you can help the person in question, even if it’s small stuff like helping spread the word about his or her next independently published chapbook.
We’ll next tackle subject that couldn’t be more crucial to freelancing (alas) …
I’d love to tell you that my drought days behind me, but I still have them. In fact, I just survived one that ended yesterday with a giant check in the mail. (Naturally, the other past-due checks have now begun rolling in, too, when I don’t need them nearly as much anymore.) You will have ups and downs, financially, no matter what you do. Your regular gigs will disappear with a switch of editors or a closing magazine. Your checks will never show up as quickly as they’re supposed to. I read it a thousand times between when I first learned the word freelance and when I actually became a freelancer: You will have ups and downs. I understood it. I prepared for it. I prepared so much that I wrote an entire book proposal and sold a book and refused to quit my day job unless I sold it for enough. And yet I still don’t think I fully comprehended how down those downs could be. So I’m going to say it a few more times, and you’re still not going to totally get it, but you may get a tiny bit closer. Ups and downs. Ups and downs. Ups and downs. They are very, very real, and they will keep happening. For real. Did you get that? Ups and downs. Most importantly, downs.
My first advice is to think about your love life. Yes, that’s sort-of a joke, but sort-of not. Are you single? That’s awesome, and you are fabulous, but this is definitely a con of single life: You have no backup system. You have freedom, and the ability to eat cheese and crackers for dinner for a week, and the sense not to settle down with just anyone. But you do not, my friend, have a backup financial system. You’re going to have to plan even better than the cohabitators. It is not an exaggeration to say that my first big freelancing down expedited my partner and I moving in together and becoming official “domestic partners.” (It was before Obamacare, and my COBRA was also ending, so insurance was a priority.) I’m not saying get married just so you can freelance, but you need to be aware of what your situation is. And if you are coupled, you should probably have a talk with your partner about what your freelancing will mean. How will you handle the down parts? We have something of a “lending” system in place, and percentages of living expenses calculated by the relative amounts we make. Is it romantic? Not intrinsically, no. But I think not killing each other over money is super romantic. Figure out whatever works for you.
You’ll also have to figure out how much you need to make per month to live. It can be helpful to break these amounts down into weekly, daily, and hourly amounts. This way you always know, ideally, what you need to make for an assignment to be truly worth it. You’ll also know when you’re falling behind, and what you need to do to make it up. The brilliant Seth Godin says you need to make twice as much as a freelancer as you’re comfortable making at a full-time job. Keep this in mind.
Maybe you’ll want to consider side jobs on occasion. I’ve known people who had “secret” freelance gigs writing pharmaceutical catalog copy, writing other boring corporate stuff, working at bookstores. I don’t really consider teaching and coaching “side jobs,” but they’re not writing, and they have saved my bank account many times.
Be prepared for the down times. Figure out what makes you feel better during those times. I get really, really dark because I feel so out of control of my life. I feel like I’m working and working and working with no reward, and this makes me despondent. It’s not pretty. If you know yoga or meditation or exercise or reading or walking or skiing or knitting or whatever helps you when you’re in a funk, reach for that when you see a downturn approaching. Those checks will show up. I swear. I started to think mine wouldn’t. Then they always did.
Which brings us to …
ASKING FOR MONEY
This is my second-least-favorite part of freelancing. Sometimes it feels just short of panhandling. Sometimes I wonder if panhandling is more efficient. Here are the times you’ll need to ask for money:
1. When you first get the assignment. Yes, as soon as they say they want something from you, get the price straight. It’s not impolite to ask. You need to know upfront so that: a. You can turn it down if it’s too low; and b. You can know what your efforts are worth. Of course you want everything you write to be a sparkling jewel. But when the chips are down and you have to prioritize assignments, the $8,000 one is going to get more attention than the $50 one. If editors want more attention, they need to pay more. If the $50 one doesn’t like this, they should have thought about that when they decided to pay freelancers $50.
2. When your editor asks you for too much work for the price. This can feel so uncomfortable because everyone wants to pretend to be making art. In the best scenario, it’ll turn out that way. But I’ve had more than one editor who essentially tried to sneak a piece from an 800-word, one-source story to a 1500-word, seven-source story. Sure, the more words and sources would make the work “better,” and we all want “better.” But my bank account wants better, too, then. You can say these things nicely, like, “This seems to go beyond the scope of what we originally discussed for the price.” But you should say something. You’ll most likely get at least a little more. Be warned: This has burned bridges for me, too. I don’t really mind them being burned, though. They were cheap. No one was hurt.
3. When it’s time to collect. Yay, your piece is in and edited! Make sure to follow up and file all the necessary paperwork. Just email them and ask what they need from you to process payment. Easy.
4. When it’s really time to collect. Okay, you did all of that, and you filed all that crazy paperwork more than a month ago, and still no check. It’s follow-up time! Drop them a line and inquire as to the status of your payment; I usually soften this with some business about making sure it didn’t get lost and/or there isn’t any other paperwork they need from me.
5. No, seriously, you’re living on peanut butter over here, you have three bills past due, and for some reason the multi-national corporation can’t manage to send you the couple hundred bucks they owe you, even though you sent your invoice three months ago. If you haven’t done this already, make sure you find the actual person who is closest to the actual cutting of the check. Editors are usually just middlemen here. They take your invoice and forward it to some person in accounting they’ve never met, then hope everything is magically resolved. You need to trace that chain of command back to whoever gets the job done. I did some of this last week, and it was miraculous. They were apologetic and sent me the official confirmation they get from, like, the machine that prints the checks, as soon as they got it.
Finally, here’s some bonus advice from my friend and colleague Bob Sassone, who has been freelancing for 30 years (basically his whole career):
Don’t be afraid to get another job, even a non-writing one, while building your career. A lot of people think they’re not a “real” writer if they don’t write full-time, which is a bad way to think. There’s nothing romantic about being a poor writer.Spell the editor’s name right, be nice, and get your articles to them early.Start your own publication/site in the field you want to specialize in. I started a homemade TV newsletter in the 90s which led to writing about TV for over 20 years.Don’t edit as you write. There’s time for that later.Reading great writers is more important than reading “how to write” books (and I’ve read over 200 of them).If you can, marry someone rich.
That’s it! This is everything I know about freelance writing as a career, or at least close to it. Have more questions? Let me know in the comments below!