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?

-Dreamer

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.

Warmly,

‘Lena

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.