Ask Alyssa: How To Start A Career In Writing By Trying Really Hard

CREDIT: AP Images/Mark Lennihan

Because I get a steady stream of emails asking for writing advice, I finally decided it was time to set up a way to collect all those inquiries in one place. The initial response was, if not quite overwhelming, voluminous. So I decided to start at the beginning: with questions about how to get a writing career off the ground. I’ll continue this in a subsequent installment. And if you have follow-ups or new questions, keep them coming!

What advice would you give someone who is thinking about pursuing a career in writing/journalism?

If you’re thinking about a career in journalism, the first step is to explore that impulse so you can be sure it’s the avenue you really want to pursue. When I’m talking to students, I always tell them that journalism has a lot in common with academia, the military, and the priesthood: all four are vocations, and if you can be happy doing a different kind of work, you might be better off doing that other thing.

But to be sure that journalism and writing are the only things you’d be happy doing, you have to try them out. If you’re still in school, go out for the paper, and try a number of different tasks, because figuring out that you want to be a journalist or a writer is just the first step in a long process of narrowing things down. Do some reporting, especially on an area outside your expertise or interest! Write columns! Learn layout! Help on the copy desk! There are an enormous number of ways to be a journalist, and some may resonate with you more than others. If being, say, a sports reporter, doesn’t resonate with you, that doesn’t mean you’re not cut out to be a writer. So think comprehensively.

If you’re not in school, there are other ways to try this out. Your local or regional paper, Patch or other local news site, or state magazine or alumni magazine may need either volunteers or freelance contributors. See if you can act as a stringer, covering things these publications don’t have full-time staffers dedicated to. And see if you can get inside the office, meet the editors, and see how the place works.

Once you’ve done one of these things, intern. I know internships can be financially abusive. I know that if you’re working or in school already, it can be hard to find the time. I know they’re insanely competitive and frustrating to get. But interning won’t just get you connections. Being inside a publication is absolutely critical to figuring out if you want to be a journalist or a writer, because it’s one of the best ways to get to know other journalists. Journalism is a profession that attracts a certain kind of person, and lends itself to the development of certain kinds of workplaces. If you don’t like journalists–I happen to love them–or find newsrooms uncomfortable places to be, that’s a critically important thing to know before launching yourself down a career path. Doing an internship isn’t just an irritating hurdle for you to jump over. It can be a real service to yourself. I wasn’t sure I wanted to be a journalist before I interned at The Atlantic, but after a summer working with my fellow interns, and getting to know the writers and editors there, I was convinced. And the editor I worked for there helped me get my first job in journalism, as a fact-checker at National Journal.

Would you suggest working on your own blog first, or contributing to an online publication?

Both! A blog is a place where you can play with your writing, trying on different tones and styles, and experimenting with new approaches to the basic forms of whatever kind of writing you’ve chosen to do. It builds your muscles and tests your commitment to the subject you’ve chosen.

But it also serves another function. I think pitching is critically important, because you want to get as many clips and as much editing as possible. But your pitches won’t always be accepted, whether because someone else’s was stronger, or because someone else’s was first. Even if your pitch doesn’t get in the door, writing it anyway gives you practice. And it means that when an editor asks you for your take on a subject to see how you’ve approached material in the past, you can show them, instead of explaining what you would have written. A blog can be great proof of your dedication and worth ethic.

Hi Alyssa. I’ve been writing for a few months now & sometimes feel overwhelmed trying to balance my writing with work, school, etc. How did you manage to balance it out once you made the decision to become a writer?

Honestly? It was not easy. In college, I wrote a weekly column for my school paper and some freelance pieces. And the school I went to offered some writing and reporting classes that let me do projects that could kind of count as features, if anyone was going to ask to see them.

My first job wasn’t a writing job: it was a fact-checking job, a sort of position I can’t recommend enough to anyone who wants to be a writer. I got to spend a lot of time with writers talking to them about their relationships to their sources, where they did research, and seeing how they piled up evidence to build arguments and narratives. And after I’d been there for a while, I started pitching my own stories and reporting them when I could. But the things I’d been hired to do always came first. That could be frustrating, but I recognized the necessity of it: the editors I was pitching to would have been–and should have been–insulted if I came to them before finishing the work I needed to do to help them.

I think the point in my career when I switched from being a trade reporter to a critic may be most helpful to you, though. At that point, I had a journalism job, and a terrific boss (hi, Tom Shoop!), who was hugely supportive of my professional development. I knew I didn’t want to be a trade reporter forever, and I thought that culture writing might be what I wanted to do, especially after a couple of guest-blogging stints, but I wasn’t sure. So I told myself that if I could write three blog posts per week day about culture, that I was serious. And I did it. Sometimes that involved coming home after work and writing. Sometimes it meant sacrificing my whole weekends. Sometimes it meant writing on my lunch break. But I made big sacrifices of my leisure time and in my personal life (which, to be fair, wasn’t extensive: I was a single workaholic at the time) to make the transition. Given the vocational nature of writing and journalism, I think this can be a good test of whether it’s something that you really want to do.

This isn’t to say you should give up everything else, or neglect your prior commitments. Writing is a career that demands a lot of mental and emotional energy, and staying right in other areas of your life is critical to doing it in a sustainable way. But if you want to write, you’ll have to look at areas where you might be able to build out writing time. And that can end up meaning replacing leisure with work.

I’m a procrastinator who wants to write but feels as though the idea will lose its relevance too soon, I really wanted to write about Dennis Rodman and North Korea, Jonathan Martin, NFL, and bullying, but feel as though the opportunity flew past me because these are issues no longer current?

If you’re trying to present yourself as someone who can respond in a timely fashion to big cultural debates (or breaking issues), procrastination is not a luxury you can afford to have on a regular basis. That said, you can sometimes find a new hook in an old story, or jump into an intellectual debate that’s unfurled around an issue. Richie Incognito’s Twitter tantrum might provide you with a new hook to write about Martin, for example. And though I didn’t get to see Frozen when it came out, the debate over Princes Charming that developed around the movie gave me an occasion to weigh in on the movie several months later. The key is to not look late, or not to look like you’ve procrastinated. You can’t just note that Dennis Rodman went to rehab and write the argument you would have written months ago. You have to have a fresh and relevant take that accounts for recent developments and intellectual debates.

On a meta level, I’d sit with your procrastination a bit. What did you do instead of write those pieces? Why did you procrastinate? Were you unsure about your arguments? The ability to cut through the noise around those issues? Asking these and similar questions may help clarify other issues you’re having with writing. Procrastination doesn’t tend to come from nowhere.

How do you find readers if you’re just starting out?

Social media and good manners are your strongest tools. I’d think of Twitter in particular as a writing exercise. One of the best ways to get noticed is to jump in productively when a debate you have something to add to, or a good question to ask, is available before you. Building your credibility on Twitter, and building a following, gives you a platform to distribute your work. And it makes folks much more likely to click on the links you’re distributing, whether they’re to your writing or to someone else’s.

That said, I think good manners are critically important to building these kinds of relationships. I get a lot of emails asking me to look at blog posts, and lots of Tweets asking me to just check something out. I wish I could do that, but I often don’t have a lot of time. The emails and tweets that do a longer look, however, are ones that readers have flagged to me as relevant, helpful, or responsive to my own writing or the subjects I work on. They make me feel like the person sending them my way knows me, has some respect for my time, and is genuinely interested in engaging. When someone contacts me out of the blue, particularly when they’re asking me to share, promote, or otherwise signal-boost their work, I know they just see me as someone with a follower count above a certain threshhold. And I tend to treat those requests with prejudice.

Relationships are time-consuming. Promoting other people’s work in a mix of your own can feel like it’s taking away from the core project of promoting your own writing. But being an interesting, serious person who other people feel invested in is the best way to build a durable audience, and a durable corps of promoters for your work. It’ll also help people understand your taste and interests, which will make them more likely to check out what you’re doing.

And I should have said this at the beginning, but work on the work. If you’re doing all of these things and developing connections, but they’re reluctant to boost your signal, take a hard look at what you’re writing. Was it late to the conversation? Similar to other things on the subject that other people wrote? Could the prose have been sharper? Better-modulated? If something’s getting a response, treat the silence, however frustrating it might be, as a kind of market research. I stopped posting trailers, for example, because I was never going to be fast as industry blogs, or as funny as I Watch Stuff and Vulture.

If a person who has never written for tv before, create, write and showrun an excellent new show on HBO, True Detective, what are anyone elses chances to do something like that?

Well, Nic Pizzolatto didn’t just come from nowhere. He’d published a novel and a collection of short stories, and he was a writing professor before creating True Detective. He’s also working with Cary Fukunaga, an experienced director. So I don’t think HBO is going to go looking for people with no writing experience whatsoever to create the next big thing. But I do think they might begin looking for folks who have strong writing or directing credentials in other areas who might bring something new to TV.