How Do Freelance Writers Get Started?

Dear ‘Lena,

For my career planning course, we’re supposed to reach out to someone in our chosen field. It’s my dream to be a published writer, but I’m already 35 and worried that it’s too late. I still feel clueless about how to get into print, even though I love to write and do it all the time. How did you get your freelance gigs? Can a freelance writer make a comfortable living, or is it more of a stepping stone? On my favorite TV show, Crazy Ex-Girlfriend, the main character has all her standup videos on the internet: whether good, bad, whatever—and you can see her get better and better. I’d like to do the same with my writing, just put it out there, but how do I begin? Is this an impossible dream?


Dear Dreamer,

If you just want to put food on the table, you can make plenty of money as a freelance writer by editing corporate marketing materials. Here’s the bad news: if you want to write nonfiction—articles for magazines and newspapers, blog posts, or a memoir—then it’s tough to make a living, even if you make your way up to writing for the New York Times and GQ. Check out this survey on how much writers make. It’s a few years old now, but print publications keep collapsing and more and more writers are churning out content online for free. So get a day job, for now at least.

Here’s the good news: it’s easier than ever before to get published.

Start a blog. This helps you to find your voice. Write about what you know about. You might be thinking: yeah, there are already a million blogs about food or fashion. So specialize. Write about your adventures in urban foraging. Write about making your own lingerie from re-purposed vintage doilies.

If you’re lucky and you work your butt off, you’ll attract enough readers to sell advertising. If not, blogging will make you a much, much better writer and provide evidence of this to show editors. Back in 2006, I had a blog about my life, which focused on my twin interests of having dinner parties and analyzing all my friends and their behavior. An editor saw it and offered me a job writing an etiquette advice column that paid my bills for five and a half years. But don’t wait for an editor to find you. Once you’ve got your blog going, you can start pitching articles.

I’m not going to rehash the rules of pitching, because you can find them anywhere online, such as here. Here’s what I wish someone told me:

Network. As with any job, this is paramount. If you have any connections at all to an editor, ask to take them to coffee to “pick their brains.” If they’ve met you, they are ten times more likely to take your pitch seriously.

Look for adventures. Don’t wait for ideas to come to you. Investigate.I went out partying with the Red Hat Society and I went to cardio strip classes—and then I pitched and sold the articles.

If you have a good story and/or you’ve met the editor, then they will take you seriously. You probably won’t get rich. But you’ll love what you do.

What Should I Leave In and What Should I Leave Out?

Dear ‘Lena,

I’m confused. My writing teacher gave me the feedback that I should make my writing “more detailed,” but then I added in a lot of details and she said that it was crammed with “unnecessary detail.” Help! – Flustered

Dear Flustered,

I can tell you about one sort of detail that always earns its keep: a character-building detail. Beginning writers don’t always realize how much a single detail—like what kind of sandwich they pick—can say about a person. Think of Harriet the Spy’s tomato sandwich (the same one every day without fail) or the comforting Swiss cheese and malted milk Holden Caulfield orders after a terrible date.

A student of mine once wrote a piece about a woman doing a nighttime stakeout. She sits in her parked car with “coffee and sandwiches.” So generic. I asked my student to tell me all about her. Then I said: “So what would this woman pack herself to eat?” Without hesitation, he replied, “a foldover”: one slice in bread folded in half around the filling. Now, with a single detail, we start to know her. She has simple tastes (she grew up in the rural Midwest). She was in a hurry when she got ready. And maybe this simple snack is something she made to comfort herself—she’s nervous. Now that foldover is even creating suspense: what’s she nervous about?

The detail in question doesn’t have to be a sandwich. It could be your character’s boots or the inside of their car or even the way they blow their nose. Think of the difference between dabbing with a lace hanky and closing one nostril with a finger and doing a “farmer’s blow” into a ditch.

Don’t be hyper-specific about everything. That would slow your story down. Just pick a few good details to focus on. Bonus: with these details working for you, you can now skip that boring paragraph where you introduce your character and tell us all about him/her, including information about their age and hair color.

That characterizing detail is especially important early on, when you’re trying to pique your reader’s interest. That’s why, when I introduce people at a party or whatever, I don’t say “You both went to law school.” I offer a detail, like “Mikayla always knows where the best food trucks are.” In stories, as in life, the kind of sandwich someone likes is way more interesting than the information on their driver’s license.

This doesn’t really answer your bigger question, which amounts to “What should I leave in and what should I leave out?” I’m afraid it takes years of practice and many drafts to figure that one out. But in the meantime: use your sandwich.



What’s the Best Writing Advice Ever?

Dear ‘Lena,

What’s the best writing advice that you ever received? The worst? -Curious

Dear Curious,

In my first college writing class, the professor said: “Write the book you want to read.” He had a sonorous voice and said everything with such gravitas that it seemed incredibly profound. Later on, when I read my notes, his advice often seemed a bit obvious. So I forgot about it.

Years passed. I published a literary novel for adults. I became a writing teacher. I was working on my next adult novel, but I couldn’t stop thinking about an idea for a different story: a girl wakes up from a dream about being able to move things with her eyes, and is disappointed to discover she’s still just her plain old ordinary self. I didn’t know how to spin this beginning into a novel.

Then someone said: “Write a paranormal romance! That’s what’s hot in publishing right now.” This was back when the lines for the Twilight movie were still circling blocks. It sure did seem like a lot of teens wanted to watch the hot vampire duke it out with the wolf boy for Bella’s affection. And heck, I could certainly do with a six-figure advance. So I dashed off a book in a frenzy. Gorgeous but standoffish hero with a dark secret. Check. Doormat heroine: Check. Gratuitous love triangle. Check.

But by the time I got the book into shape to show my agent, she responded by emailing the link to a Publisher’s Weekly article about how paranormal romance was out. In: contemporary realism, preferably featuring teens with cancer. Thanks, John Green. My stomach dropped. Much as I’d admired The Fault in Our Stars, there was no way I could turn Sparked into that kind of novel. I’d been a fool.

I learned the hard way that chasing a trend is never a good idea. Predicting what’s coming next in publishing is as impossible as trying to guess the new cut of jeans. How many times have you been duped by a book billed as “the next Gone Girl“?

So, back to my agent’s scathing response. I spent a few days despondent. Then I remembered that bit of advice: “Write the book you want to read.” I liked to read books with complicated, flawed characters, dark humor and sense of mystery. I realized that I found my own hero intensely irritating. His leather jacket. His curling lip. His disdainful treatment of my heroine. And why were his green eyes always flashing?

And I also saw that it wouldn’t be hard to take out some of those paint-by-numbers plot points I’d put in (goodbye, love triangle) and reshape my characters into three-dimensional human beings. But I could still preserve the parts of the book I loved—the parts that made writing that first draft such fun. I spent over two more years on rewrites. But because I was writing about characters that I wanted to spend time with, I enjoyed every minute.

If you write the type of book that is hot this year, it will be out of style by the time you’re ready to publish it. So here’s the best ever writing advice: don’t write a book you think will make a million bucks. Write the book you want to read. Chances are, if you do this, other people will want to read it too.

Should I Finish My Book?

Dear ‘Lena,

Answering either one of these questions would help me out a lot:

1) Is it a normal part of a writer’s life to be surrounded by a great deal of flammable material, or should I be worried? I have several tons of worthless drafts on paper, plus a mountain range of books by authors who actually can write, baffling research materials and what-not laying around.

2) Do you know of any writers whose death-by-spontaneous-combustion was linked to daily fears about mass humiliation? – Burning With Insecurity

Dear Burning With Insecurity,

It’s totally normal to feel intimidated by the greatness of other writers. A friend of mine once tried to escape from this feeling by turning all the books on her shelves around – so their well-chosen titles weren’t “taunting” her. Of course, all this did was create a creepy vibe.

So what can you do? Stop comparing your rough drafts to published work. It doesn’t make any sense because you’re comparing two different stages in a process. It’s like comparing lumpy, pasty batter to a triple-layer strawberry genoise.

That pile of “worthless” drafts you have? Far from being an embarrassment, it’s actually a sign you are a true writer. Most authors write dozens of drafts. I once went to a talk by famous children’s author Jack Gantos in which he claimed to write one hundred drafts of every book. Working your way through even fifteen drafts might seem challenging, but bear in mind that only a few of these drafts will be major rewrites. Many of them will just involve sentence-tweaking.

And don’t think that “real” writers always enjoys this process. Just as writing can give you amazing highs, it can also make you experience terrible lows. One very successful writer I know can only finish a book by plastering himself with nicotine patches and locking himself in a closet with his laptop. He usually has scratched off his eyebrows by the time he emerges with the final draft. My point? Your angst is totally normal.

So when you pull a book from your shelf, remind yourself that you’re actually reading the 100th draft of a novel that could have been turned into kindling early on. One of Steinbeck’s original titles for Of Mice and Men was Something That Happened. Before he chose The Great Gatsby, Fitzgerald considered calling that book The High Bouncing Lover.

As for your fear of publication, the reason you feel afraid is that you’re imagining people reading your work as it is now. But remember that cake metaphor? I didn’t use it just because I’m obsessed with food. Writing a novel is much like baking: the end result often bears little resemblance to the beginning. Somehow a mass of bad writing, flat characters and clunky coincidences becomes a story with character arcs, resonant metaphors and thought-provoking themes. It might feel hard to believe now, when your raw ingredients are scattered around your work area. But when you do publish your book, you will have transformed these ingredients into something you are proud of. With any luck, you’ll still have your eyebrows too.


Should I Toss My Embarrassing Journals?

Dear ‘Lena,
I’m fourteen, and I’ve been keeping a diary since second grade. Recently my mom told me to go through everything in my room and throw out whatever didn’t make me feel “joyful” (her word–weird I know). I started reading my old diaries, and was horrified to find that the writing is truly horrible. The middle school ones are the worst, all about crushes on guys I can’t stand now, and girls being mean. I want to be a writer, so this was really depressing. I kind of want to get rid of my diaries and start over. It’s not like I expect biographers to come knocking, but if they did, I would NOT want them to see anything in this “early work.” Is there any reason to keep them?

-Not Anne Frank

Dear NAF,

First off, don’t be so hard on yourself. A diary is meant to be a place to write without censoring yourself, to vent and muse, record observations and feelings. It doesn’t have to be literature.

By her use of the word “joyful,” I suspect your mom read a book by this Japanese organizer who promises that a life without clutter will be more serene. She might be right—but you’re fourteen. You’re supposed to have a messy bedroom and record your crushes in a diary with a teeny lock that doesn’t work, resulting in your “friend” reading it after you fall asleep one night during a slumber party, and spreading the stories of your unreciprocated crushes all around middle school.

Oh wait, that’s me I’m writing about. I too kept a diary, and the writing in it was truly awful. I know this for a fact because my own mother recently moved to a new house and sent me my old diaries. While I wasn’t thrilled by their (sub)literary quality, it was interesting to see these records of my bygone thoughts and feelings—like rough drafts for the person I am now.

And while most writers would probably shudder at the thought of their journal being published, a writer’s journal is the mine from which we dig up treasures that make our real writing sparkle. In Sparked, the mom has a boyfriend who wears skull rings, and he likes to squeeze his fist to admire them. I got that detail when sitting next to a menacing guy on a bus who was doing just that, and I remembered it because I jotted it in a notebook.

Your journal can also help your writing in another way–by giving you insight into how we feel at different ages. Let’s say you wanted to write about a nine year-old. You could go back and read your diary from third grade, to remind yourself of what mattered to you back then. Remember how you pined for the friendship of that one popular girl so much so that you gave her the crepe paper flower you were supposed to make for your mom for Mothers’ Day, and when she took it from you she looked at it blankly and said, “What am I supposed to do with this,” before throwing it away?


Oh wait, that’s me again. That was humiliating at the time, but maybe I’ll use that detail some day. Or maybe I won’t–that’s OK too. Writing a journal trains you to observe other people, to remember details and dialog. So throw out your old stuffies, if you must. Get rid of board games with missing pieces. But keep your journals–yes, even the middle school ones.


Do I Need to Write Every Day?


I really want to be a writer, and I love to write, but I heard that if you want to do it for a living and get good, you need to write every day. I don’t always have time to write every day, and I worry that I don’t have enough to write about. Do you think that it’s essential to write daily? How often do you write?

– Wrist Cramps

Dear Wrist Cramps,

Writing is like working out—you don’t have to do it every day but you do have to do it regularly. That means you don’t sit around and wait until you feel like writing, because that will probably never happen—any more than you will just feel like putting on your running shoes and going for a 5-mile jog. (Congratulations if you are the kind of person who can’t wait to lace up her running shoes, but you are not normal.)

The key to getting fit—and to becoming a writer—is to put it on your schedule. I mean this literally: put it on your Google calendar. Set a reminder on your phone. Write it in your diary if you are an analog person. When and how often? There’s no one-size-fits all answer. Maybe you like to write when the house is quiet, so you write four times a week from 6-7 AM. Maybe your imagination is most active in the evening, so you put in a couple of hours between 8-10 PM.

Whatever your schedule, if you’ve already made the decision to write, then you don’t have to use your willpower to psych yourself up every time you write. It’s a habit. You just do it, the same way your CrossFit sessions or cook dinner or take out the compost.

You may be wondering why I am comparing penning the Great American Novel to dumping out a container full of banana peels, globs of oatmeal and other gunk. It’s because writing isn’t always fun. In fact, it can be downright unsatisfying and unpleasant. But if you’re a real writer, you just sit down and do it, even when you would rather lick the bottom of that compost container than pound out another word.

But here’s the good news. You know the “runner’s high”? Writers get a writer’s high: you enter the magical world of your own creation and everything else falls away. I call it being in “the Vortex” and it’s one of the best feelings there is. You won’t get that high the first few times. You have to put the practice in. And then one day you’ll realize that you’ve written far past your allotted time and your bedroom is a mess and you haven’t had a shower for three days and your last two meals have been stale tortilla chips eaten out of the bag. Congratulations: you are a writer.