Writing Practice #1: Charley Locke

Charley discusses idea generation, “networking,” and turning to poetry in overwhelming times

Hello and welcome to the first installment of Writing Practice, an interview series about the interplay between embracing creativity and earning a living.

I’m honored to have Charley Locke as my first guest! Charley is a narrative journalist, editor, and story producer. She often writes about what it’s like to grow up and grow old, though she’s also explored the utility of the Notes app, immigrant families on Martha’s Vineyard, sports gambling, and more.

I love that Charley’s work reflects her interests at a given time and doesn’t follow a narrow beat. She’s a contributing writer at The New York Times Magazine and writes features for publications including Bloomberg Businessweek (my alma mater), The Atlantic, and Vox.

Charley and I first met in October of 2023, after I came across a tweet (on her now-deleted profile 🫡) about her journey to becoming a freelancer. At the time, I was beginning to contemplate my own career as an independent writer, and when I emailed to ask if she would chat she kindly agreed. On a rainy day that fall, I called her from the Capital One Cafe at the base of my office building so my colleagues wouldn’t overhear. Our conversation gave me the confidence to seriously consider quitting to do my own thing.

We caught up again in January about the ebbs and flows of freelance work, making connections with new editors, and our shared habit of sewing in the middle of the work day. Our interview has been edited and condensed for clarity, and I’ve included some footnotes throughout.

OR: What launched you into freelancing initially?

CL: I started freelancing because I got laid off during the pandemic. The magazine where I was working — Pop Up Magazine — which was a live magazine for the stage, didn't work during the pandemic. Pop Up downsized a lot during the pandemic, and I got laid off in October 2020. I started freelancing, just as a stopgap to figure out how to make money and what to do next. To my surprise, four years and change later, I still really, really like it. It continues to work out really well for me, and like, be the best job I've ever had. I never would’ve had the confidence to step away from a staff job unless I had been pushed out of it by being laid off, but in the end, I'm really, I'm really grateful.

OR: In the early days, did you rely solely on journalism, or were you doing other copywriting and editing stuff too?

CL: For the first probably eight months that I was freelancing I had one kind of halftime contract gig where I was working on this podcast 70 over 70.¹ It was something like 20 hours a week. That was a really helpful anchor gig for me. And then I was writing for the New York Times for kids a lot too.

Now, the balance shifts every few months. It's different. A big portion of my income now comes from non-journalism stuff, whether that is writing case studies for companies or editing blog posts. Sometimes I edit speeches or performances and help people figure out how to tell their stories on stage. One thing I really like about freelancing is that it feels like I can move the lever on how much I am doing non-journalism, work which often pays well, and journalism work, which is the stuff that I really love.

There are seasons where I take on a bunch of copywriting and non journalism stuff because I want to be investing a lot of my time in working on a journalism pitch that isn't assigned anywhere yet. In those cases I need to just like bankroll myself temporarily. And then there are periods where almost all my stuff is journalism, and it's assigned shorter features or projects for different editors who I've worked for.

There's so much conversation about how dire the state of the journalism industry is, which is true in many ways, but I think that to me, freelancing feels like more of a safety net. It helps me plan for a wide future of different kinds of work that I could do, because there are probably going to be times in my future when I care about making more money and maybe there are times in my future when I really need to have great health insurance and benefits, and then I’ll want to try and get a staff job somewhere again. The days of being handcuffed to a staff writer job for 25 years feel a bit archaic.

OR: What has been your strategy for meeting editors? What's the balance between cold pitching versus being like, I know this person from that guy who knows this person?

CL: Cold pitching is so, so hard. I have not had a lot of luck with doing that. So much of getting your stories accepted, in my experience, is when the editor knows they can trust you. They know you’re someone who is going to be a conscientious reporter, turn in clean copy on time and, work on edits with them, give an annotated draft to the fact checker, and basically, be someone who is pleasant to work with and makes their working life easier.

I’ve had to figure out my own version of networking that feels good to me. That word feels so gross. When I read something that I admire, I write to the person who wrote it, or write to the editor who organized a project or worked on a package or whatever. I tell them why I think it's great. It's not that I'm writing text with the editor being like, ‘Hey, I liked your package, I'd love to get you this idea.’ It's more like, ‘Hey, this is amazing. I thought you tackled this aspect of this challenging story really well.’ I'm not doing this in a calculated way. But then, a year later, if I have an idea that is a good fit, I’ve introduced myself in a way where I just really admire what they do.²

I don't live in New York.³ When I go to New York once or twice a year, I reach out to a bunch of those people and ask if they have time to get coffee with me and talk about ideas. For example ‘I wrote to you four months ago when I loved XYZ thing you did, and I've been thinking about ideas along the lines of XYZ. I'd love to talk to you about it if you have time to get coffee.’

OR: Would you say that you work a full 40 hour week? Or do you build it out differently every week?

CL: It really goes through enormous ebbs and flows. I have periods where, if I'm working on two different features for different magazines and doing whatever other little work in terms of editing blogs or whatever other stuff I'm doing for companies, I am working way more than 40 hours. There are also plenty of weeks where I'm working 15 hours or something, and also spending a bunch of time — I don't know if it really counts as working or not — where I'm reading nonfiction books and thinking about what other stuff I want to write. Or I’m reading a bunch of fiction and going on a walk, talking to friends about ideas to try and figure out whether there's a story there.

This is definitely my slow period, these months at the beginning of the new year. I think it’s really nice to be able to lean into that in the winter. I do a lot of reading and thinking about stories I want to do. I’m looking for interesting subjects, I'm doing sewing projects, and I go skiing a lot. And then, for me, because of the subjects I cover, the months before back to school are incredibly busy.

What about you? What does it look like for you?

OR: I try not to work more than 35 hours a week in terms of time that I'm at my desk writing stuff, or, like, sending emails, or whatever it is. That basically means I work every weekday and stop midday Friday. But I'm also in grad school on the weeknights, and that is a lot of writing which might eventually be commercialized.

I'm kind of working all the time, but not in a way that I'm overworked, which is such a different feeling than when I was a staff writer. Even though I might work more hours, it feels so much freer, because I’m on my own time. Sometimes I make a schedule, and then I decide I want to go to yoga, so I'll do a little task on Saturday instead.

Do you do other personal or creative writing that you fit into the week as well?

CL: Not a lot. When I'm done working, it’s not really what I want to do. In some ways, I miss doing that kind of writing. I do it sometimes, but it's more when it just feels urgent to write. But I do other kinds of creative stuff. I've been sewing a bunch. A funny thing about freelancing is when I realize it's 2 p.m. and I've just been sewing all day. ⁴

OR: You mentioned earlier that you sometimes talk to a friend about a story idea. Do you have a kind of method to the madness when it comes to coming up with ideas or honing a pitch?

CL: I keep a lot of weird strings of things that I should look into on my Notes app. And then I also have a big piece of paper next to my desk where I'm just constantly jotting stuff like that down.

One of the scary things about freelancing for me at the beginning was this idea that you're totally isolated on your own, and then you send an idea out into the void to an editor. I work really hard to have that not be what it's like.

I have a bunch of friends who I really think of as colleagues. Some of whom I've worked with at other places — like either when I was on staff or people who I've worked with or for as a freelancer — and some of whom are just kind of friends who I've met through other journalism, press and stuff like that. Every week I talk to at least one of those people where I'm just talking through ideas. It's enormously helpful. The more you can do this in community, the better. It’s a lonely and hard job if you don’t lean on other people.

And when you have established relationships with editors, you can be like, ‘Hey, I remember you mentioned that you have a special issue on education that'll come out for back to school in September. Do you have 20 minutes to talk on the phone about a few different ideas?’

OR: I know you've written some stuff that has your first person perspective. How do you determine when it’s the right time to put yourself into the story?

CL: Ninety-five percent of the stuff that I write is straight reporting. I'm not in it. Maybe once a year, every two years or something, I have an idea for something like that percolates for a really long time inside and it feels like it just wouldn't work as a non-personal essay.

For most stuff, I prefer straight reporting but my personal life comes up in my work all the time. It helps me establish an argument or perspective. But in general, I really parse the world through thinking about other people's stories and other people's perspectives. I don’t have that much to say about my personal life.

OR: Do you feel like you have a specific beat these days, or do you just follow your interests?

CL: I write a lot about older adults and kids. It feels sneaky to call that a beat because those are two populations that are basically experiencing everything. ⁵ I am really a generalist in terms of my interests. I just like writing about meaningful stuff people are going through and what feels urgent. The one place a beat is really helpful when you’re pitching editors. When you put yourself in their shoes, you need to prove that you can pull the story off. But if you do a good job, then you can write about anything.

I like writing about what it’s like to grow up and grow old because a lot of journalists aren’t covering them as stories. There’s not as much writing about being a kid from a kid’s perspective or what it’s like to make friends in your 90s.

OR: Do you feel financially secure as a freelancer?

CL: I do feel financially secure and it’s been really clarifying to see how freelancing basically means having a bunch of jobs with different percentages of my income. I think anyone who’s been in journalism for a while has been burned or knows a lot of people who have been burned by layoffs and how hard it can be. Even if any of the places I write for fold, nowhere is more than 30% of my income.

Good Content by Charley

Read

• Diary of a Void, by Emi Yagi: Absurd, sharp. It feels like she opens a trapdoor under the impossible expectations of being a woman in your 30s

• Reboot by Justin Taylor: The rare book that makes me genuinely laugh aloud, so smart and full of heart

• Mating by Norman Rush: A brilliant, challenging delight, a book that you can spend a whole weekend subsumed in while also googling words like "carking" and "vitiate"

Poetry

CL: When the world feels overwhelmingly insane (like now), I also often read poems, which can hold my focus more.

• “The City Limits” by A.R. Ammons

• “Proof” by Tiana Clark

• “When I Tell My Husband I Miss the Sun, He Knows” by Paige Lewis

P.S. Check out Charley’s great NYT Letter of Recommendation on poetry here.

1. Max Linsky, the creator of 70 Over 70, was also on the team that made Longform (RIP), one of the inspirations for this newsletter.

2. I asked Charley after our chat how she finds the editor on a particular story, since they’re not usually listed: Social media! Editors often post a package they worked on, saying something like, "New package on TK thing! Loved working with writers including TK, TK, and TK. Read now for TK!" Writers also often tag/mention the editors who worked on their stories when they post stuff.

3. Charley currently lives in Portland, Oregon, but she travels and works around the world. Read more about her adventures on her Substack here.

4. Charley and I both have this habit. Sewing is the one thing that can suck me in deeper than a writing or editing project, though often out of frustration over enjoyment…

5. Check out Charley’s incredible stories skydiving seniors and teenagers growing up in the climate crisis.