A Q&A with Charlotte Wilder of SB Nation on her climb up the journalism ladder and writing about the “fringes of sports.”

Every week we will run a Q&A with a wonderful reporter to talk about what’s right and wrong with journalism, their interests and random other stuff. Some are friends. Some are just people whose work we really respect. Some cover sports. Some don’t. Hopefully all will be interesting.

This week, it’s with Charlotte Wilder of SB Nation. Charlotte is something of a Renaissance woman. She’s a fantastic writer, an excellent photographer and truly versatile journalist perfect for the modern media landscape. Unlike many of our guests, she didn’t necessarily aspire to write about sports, but we’re all lucky that she wound up covering them. Here, we discuss her unusual career path, the stories she chooses to pursue and how to take a great food pic for Instagram.

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The questions are in bold. The answers are not.

1. We start all our Q&As in the same way—at the beginning. So: How did you break into journalism, and what led you to where you are now?
I’ve always known I wanted to be a writer. My mom was a journalist and used to bring me on reporting trips with her. She took me to a dog sled race in Wyoming, to see how churches in Venice get restored, to watch dancers from the wings of the New York City Ballet. I grew up watching this badass woman ask questions and tell stories in a male-dominated field. I never questioned whether it was possible.
I had to take a circuitous route to do it, though: I went to Colby College, which I loved, but it was limited in terms of connections to the media world.  When I went into the career center, the Very Important Career Man asked me what my dream job was. “On staff at Esquire,” I said. He goes, “Hmm, well we don’t know anyone in that world, but we do have a ton of connections to the insurance world in Portland, Maine!”
I also didn’t do myself any favors because I was focused on poetry and photography in college; I thought I was going to be a poet or get my MFA in fine art until I was like, “Wait…how does one be a poet? And why can’t I remember how to use Photoshop? And why am trying to do either of those things when all I want to do is go places and meet people and write about it?”
But I hadn’t had any summer jobs in media or been the editor of the paper or done any of the things you’re supposed to do if you want to work in this field. So during an internship I had at a literary agency right after I graduated, I’d finish my work by, like, 10 a.m., and then post on my blog that I’d started during my junior year of college — photos, essays, interviews — five times a day or so. It makes me cringe to read now (and it’s not online anymore so don’t even try to find it), but I loved doing it, people read it for some reason, and it got me freelance jobs at Boston Magazine. The catch-22 about breaking into this business is that no one gives you a chance if you don’t have clips, but it’s hard to get clips if you don’t have clips. My hope was that my blog would show I could write and was obsessive enough to do it on my own.
The landscape has changed so much that I don’t know if this career bushwhacking approach would work today, but six years ago it did — based on my blog and freelance work, America’s Test Kitchen hired me as a web editor for its TV show and its two magazines, Cook’s Illustrated and Cook’s Country. I was there for about two years, then Boston.com hired me as a general reporter in 2014. USA TODAY Sports became aware of me and hired me away from Boston.com in March 2016 (when I officially became a sportswriter, I guess), and then SB Nation hired me away from USA TODAY after seven months. I’ve been at SB Nation since November 2016.
It’s been kind of a wild ride; I had three different jobs and lived in three different cities last year. But I haven’t taken a single day at any of these positions for granted, and I try to go as hard as I can, because I know it could all go away. I remember what it’s like not to have this career and desperately want it.
2. You do a lot of experiential, first-person work, which is awesome. Your story on going to the Kentucky Derby earned wide applause. It was great. We also liked other stories, like you watching WrestleMania for the first time. We enjoy them because you’re not lying to the reader that you’re some kind of expert or trying to fake your way through something you’re doing for the first time. Fresh eyes are a great way to explore a topic. Do you ever worry about reporting and writing about something you’re not familiar with? How do you balance the story being about your experience and about the issue itself?
Thanks, first of all, for the kind words. That means a lot, because I know that when I do a “stranger in a strange land” type of piece it’s a very fine needle to thread. My nightmare is coming across as though I think I know someone’s home better than they do or sounding condescending. I think that’s why I turn to humor a lot with my work in general. I find making jokes a much more effective way to cut someone powerful down or expose something than standing on a soapbox.
When it comes to writing one of those pieces, though, the first thing I do is assume that I know absolutely nothing. I research the hell out of what I’m covering before I get there (except WrestleMania — went in totally blind to that for the effect of being totally blind). I read everything on the Derby that I could find and talked to a lot of people from the area and some folks involved with the race before I went there. I always want to honor the places and people I write about by being as well informed as I can be, and, once I get there, by asking as many questions as possible, even the ones that seem obvious. Asking obvious questions is, I’ve found, when I get the most surprising answers.
I think writing about subjects I have no expertise in is effective because it makes me question certain things that people who do know them have taken for granted. I also try not to have an agenda or a preconceived notion of what I’ll find when I go somewhere — I’ll have an idea, of course, about where the story will go, or what the themes will end up being, but I’m always thrilled if I get somewhere and find out that I was completely wrong. Being willing to scrap an idea and pivot depending on what you find is a the key to being a good and honest reporter, I believe.
I don’t ever want a story to be about me; I’m not the point. I try to use my lens and my experience of attempting to figure something out as a way to bring the reader along on that discovery process. I hope that’s how it comes across. I don’t know if it always does. I’m sure there are people out there who think I’m a hack who writes about herself, but fingers crossed that it lands more often than it doesn’t.
3. A quick Google search for your name shows that you’ve worked at and written for a lot of places before reaching SB Nation (including America’s Test Kitchen — what was that like?!). Is it fatiguing to have spread yourself across so many outlets? Also, our sense is that journalism’s business model will leave fewer full-time jobs available and lead to much more freelancing, leaving writers to be much more self-sufficient. What is the freedom in having more versatility and the difficulties in not having a true home that gives you benefits and a set salary?
Well, I do have benefits and a set salary. I only freelanced full time for about six months when I was fresh out of school — other than that I’ve been full-time on staff at every outlet I’ve worked at, for which I am beyond grateful. I know that’s rare these days. I haven’t felt fatigued, though; if anything it’s been invigorating to get to write about so many different things at so many different places and work with a variety of editors.
I feel so lucky to work with so many people I love at SB Nation,and to feel like they believe in the stranger things I try to do. They send me around the country so I can tell stories. It’s my dream.
4. You’ve written a lot about non-sports stuff — art, food, trains — which makes me jealous. How do you think writing about different topics and issues improves your writing? Do you think that kind of variety should be encouraged? Especially for sportswriters — to get their head out of writing about transactions and games and try to see the world a little? 
Well, until I worked at For The Win, I wasn’t a sportswriter. They kind of took a chance on me — Nate Scott, who’s a fantastic editor, was there at the time, and he vouched for me, even though I don’t think I even knew who James Harden was at that point. My background is in culture writing and general reporting; I wasn’t really a huge sports fan before I entered this world. I liked sports, and I understood sports, and I played sports, but I wasn’t immersed in the news cycle. I didn’t really pay attention or watch that many games, to be honest. It was kind of a leap of faith to make the jump into this field.
Learning the characters, the narratives, the storylines of this insane industry was like drinking from a fire hose those first six months; it kind of felt like getting a master’s degree in sports. I’m up to speed now, but at the beginning I was like… who the hell is D’Angelo Russell and why is Nick Young mad at him and what does this have to do with basketball? My editors at FTW were very patient with me as I Googled every single person in the news hits I had to write. And I’m sure I still sounded like a total moron early and often in the beginning.
Veering into sports has been, hands down, the best decision I ever made. I love sportswriting because it can encompass so much. I joke that “____ is sports” on Twitter a lot, but it actually came from a pretty earnest place. Sports isn’t everything, but it is a lot: I mean, look, I get to write about “The Bachelorette,” I got to go cover the Super Bowl, I wrote about Kentucky Derby… I’m working on a story about fishermen in Maine right now. The stories in this world can be as silly or as serious as you want them to be.
When it comes to subject matter, I’m not picky; I just want to write about things that people care about, or take them into a world they don’t yet know they care about. People always care about sports, and they’re often a huge part of the national conversation. I always feel like I’m in the mix.
But, to answer you question: Yeah. I think there’s a lot of value in writing about something you don’t know because it forces you to really dissect something and make an effort to understand it. If sports is what you know, maybe get outside it for a story, or write about an aspect of the games you cover that you normally wouldn’t. Sports still surprises me that way. For example; the NBA draft lottery rolled around and I was like, “Wait, that’s how this works? That’s so dumb.” And my coworkers were like, “Ha, we just accepted it because it’s what we’ve always done, but you’re right, it is dumb. Write about how dumb it is.” So I did.
Get outside your bubble every once in awhile, because when you go back into it, it’ll make you look at the things inside with a different lens.
5. So, apparently, you worked at a job for literally one day then quit. What was the job? What were the circumstances? What do you consider when you’re switching jobs?
Ha, oh man, where did you find that? Did I say that publicly somewhere? Guess I did. Man, I can really run my mouth. Well, here’s the story: After my internship at the literary agency, I was like, “Hmmm maybe I should get a job so I can, you know, move out of my parents’ house and feed myself.” So I convinced an email marketing startup to create a position for me — me! A 22 year-old kid! I showed up on the first day and spent the whole time posting on my blog. I realized I didn’t give two shits about email marketing as I sat there — I was almost blacking out because I got so panicked, thinking, “I’M SUPPOSED TO BE A WRITER!”
My boss called me into her office and was like, “I’m so glad you’re here, and I hope you’ll be just as passionate about email marketing as I am.” I looked up and there was this big-ass word cloud above her desk that said, “Do what you love” and “Live the dream” and all of that. I remember calling my mom and being like, “You need to meet me at this bar after work because I need a drink.”
I got there and my mom had a glass of wine waiting for me and I was like, I can’t go back, I need to be a writer, I really think I can be a writer. She was like yeah, I agree. So I sent the company an email saying I didn’t want to waste its time. The company was like … are you serious? It’s been a day. And I said, “Yeah, goodbye forever.”
From there I convinced a few small businesses to pay me to do their social media while I worked on my blog until I eventually got hired by America’s Test Kitchen (the social media stuff was such a racket — I’d, like, schedule tweets on TweetDeck and call it a day). Oh, there were also three weeks at a PR firm in the mix there, but that’s a whole other story. Basically: I was kind of a con artist in my early 20s, but hey, it all worked out in the end.
6. You said once of your career that “my story is one of privilege.” You lived with your parents after college in pursuit of a writing career, worked on your personal blog and tried to get everything up and running. Obviously, that worked out well for you. Breaking news: Going back to living with your parents after college kind of sucks, especially if your friends have jobs and apartments. But it seems like that’s kind of normal for young writers, especially since jobs are hard to come by and salaries keep getting depressed. What was the calculus you made in choosing how to pursue your career and the financial toll that would take? Any advice you’d offer to people just out of school or about to graduate who might need to figure out these same decisions?
Yeah, mine is definitely a story of privilege. My parents let me live at home and eat their food for a year while I got my career off the ground. It was a huge help not to have to pay rent as I scraped together clips and worked on my blog. I was able to devote all my time and energy to getting where I wanted to go because my family was financially able and willing to support me.
I often tell people who reach out and ask for advice about doing this job that this career is more of a compulsion than it is a choice. You can make so much more money doing something else. Almost any industry is more stable than media right now. This is something you do because you love it so much that you can’t see yourself doing anything else. Because you start blacking out when you try to take another job in email marketing. I think you  have to be a little bit nuts and a whole lot driven.
So if you have that drive, and you’re determined to do it, go for it. Sure, it’s a shitty time in the industry, but there are jobs, and if you’re multi-faceted — and can do stuff like video editing, podcast editing, social, in addition to writing — that increases your chances of getting hired. But you have to work your ass off, and it will become very clear to you very soon if you’re willing to do that.
This is such a competitive field. That said, talent does rise. I’d suggest developing your voice and making what you do very clear. I write about the fringes of sports and have kind of found this strange lane, which helps differentiate my work, I think. That’s been helpful for my career.
I hate when established writers tell kids “Don’t do this,” because a ton of people said that to me when I was trying to get my foot in the door, and I was like … no, I’m going to do this. Telling me not to do this isn’t going to stop me, it’s just going to make me determined to prove that I can.
So I say: Do it. Try your hardest. But know what you’re getting into, and that it’s probably going to require a ton of work for not a ton of money for a while.
7. It seems like you have real photography skill and have invested time and money into it. But also, you have a vibrant Instagram account. I’ve read you talk about food photography and especially the food pic on IG. Let’s try to settle this once and for all, because I think Jared and I have had this conversation before: Is the food pic pretentious? Even if it is, what’s the key to a great food pic? And what’s the most shame you’ve ever felt while taking one?
Yeah, I thought I was going to be a photographer for a while, and I still take a lot of the photos for my features. But in terms of food pics, I don’t know…I think they’re pretentious if you’re a douchebag. If you’re a nice person and you’re like, “Hey, check out my avocado toast!” then who cares? (But I guess that’s how anything works…if you suck I’m probably going to hate your Instagram). I don’t know, man, I guess I just generally don’t really care what other people do if it isn’t harmful to anyone else. If you want to Instagram your Pumpkin Spice Latte, go for it. Do what makes you happy. Am I going to make fun of that photo of your acai bowl? Yeah, I am. But don’t let that stop you.
Yes, I feel like a total asshole when I stand up at a fancy restaurant and take an aerial shot of a goddamn pizza. I post fewer food pictures now, but the key to a good one? Probably good light. But the key to a good picture of anything is good light. Maybe, like, an array of plates. Some runny egg yolk. A big ol’ piece of bread flanked by wine glasses. Go nuts.
8. You wrote a fantastic story about the Patriot’s Trump problem. What was the feedback you received for that story, not only on Twitter — I’m sure I can guess how that went down — but also from your friends, family and your community? As a native Bostonian, what was that story like to write and also to put the place you represent under a microscope?
Oof, that was a doozy. I actually don’t like to talk about the fallout that much because it all came from one radio station in Boston and I don’t want to start the feud back up again. But it got really nasty and personal and definitely felt like it had to do with the fact that I am a woman. I think I’ll write about it someday, because it got at a lot of things that drive me crazy about this industry and that I think are worth exploring. For now I’ll just say that I got a barrage of garbage on Twitter, and my parents got hate calls from angry listeners at their house in Massachusetts and had to go to the police, and it was truly awful.
The more rational reaction aside from that, though, was mixed. I had some friends in Boston who were like, “Yeah, I agree, the team’s connection to Trump is a problem for me.” But I had others who were pissed that I wrote it, who felt that I was accusing them of being bad people if they still liked the team, which I wasn’t. What bothered me the most was that some people took it as an opinion piece rather than reported analysis, even though I never said how I felt about all of it. Sure, I hate Trump, but I didn’t include my views on the team’s connection because I was really conflicted; I still loved the team through it all.
But to answer the second part of your question: When it comes to writing about a place I’m from, that’s the only time I feel like I know what I’m talking about from any point of any expertise. You asked earlier about writing about stuff I don’t know, and I honestly feel that way with every piece that isn’t about the culture of Boston, or Maine, where I lived for a while. Or the boating world which I worked in from the time I was 15-22 in the summers. Or Boston sports, or poetry, or hot dogs. I have a few things I know, and writing about them allows me to really get in there and root around in the psyche of the people who live in the place or do the thing, because I have the context and shared experiences to be able to understand it from the inside out rather than the outside in.
The stakes can feel higher when I write about what I know. There’s as much pressure to do what I know justice as there is with writing about something I’m unfamiliar with, but this time, if I mess up, my friends and family are pissed rather than strangers. You only get to write about home so many times and I care about home more than anything. I don’t want to fuck it up.
9. What, if anything, do you think should change about the way sports is covered?
I wish there were more positions for writers doing ambitious, big work that takes time. I also wish it didn’t feel like the industry were burning down around us; every day it seems like writers I’ve admired forever are getting laid off or fired because people high up are making stupid decisions that don’t make sense. I know at some point in my career I’ll be laid off — I just hope that there will be a job for me somewhere else when that happens. Or maybe I’ll just say to hell with it and become a lobsterwoman in Maine.
I am so, so, so, so lucky to be in a feature-writing position. But most jobs come with quotas, or a certain amount of requisite blogging, to drive traffic.There are a lot of young writers getting ground down by the blog mines and the daily churn of the content factory who aren’t getting a chance to develop storytelling chops, or to work on more ambitious projects because places won’t fund them.
You gotta drive traffic; I get that. I just wish it weren’t so grueling for so many people (and that so many spectacular people didn’t keep losing their goddamn jobs). I certainly put my time in doing that, but it kind of turns you into a shell of a human after you put 5,000 on the internet that you wrote in the span of eight hours and then go home to work on a feature because you want to show people you can, and if you don’t do it when you’re not blogging, when are you going to do it?
That’s not sustainable. This industry needs to be better at supporting development for writers more. Editors matter. Don’t cut those positions.
10. You’ve done several tag-along stories with athletes as they do some kind of promotional appearance and you get some time with them. With David Ortiz. With Noah Syndergaard. Whatever the hell JD & The Straight Shot was going for. How do you get these guys to break down a little? And what’s your approach when you know they’re just trying to sell product (or give the impression they definitely don’t know who the Knicks are drafting)?
I said earlier that I use humor a lot to try to upend a situation and make people think about something differently. I definitely do this with athletes, too; I’ll make a joke off the bat, try to make them feel comfortable with me. They’re usually so guarded, and rightfully so. I want to make it clear to people that I won’t ever actively try to screw them over. I will, however, report the truth, so if you end up screwing yourself over, I’m not going to save you. I try to call it like I see it.
In terms of promotional things, I get that this business, when it comes to access, is often based on PR stuff. So if I have an opportunity to hang out with Ortiz and it’s because of a book signing, fine. But I’m never going to write the, “buy Ortiz’s book” piece. I’m going to write the “here’s what I think I learned about Ortiz by tagging along to a book signing.” And I usually turn down blatant product pitches — the only reason I did the Syndergaard thing is because I thought it was so funny that he’s sponsored by Cholula. Who gets sponsored by HOT SAUCE? It cracked me up, so I went to try to figure it out. And it turns out the dude just loves hot sauce.
I also think I have a knack for getting people to play along with me, if that makes sense. Once someone realizes I’m not out to get them, they’re more willing to joke around and have a fun conversation. I love talking to people and figuring out what makes them tick, so spending time with athletes is kind of a challenge; can I get this person to open up? And if they do, can I do justice to what they say? And if they don’t, can I at least get something funny out of it, even if it ends up being, “Hey, look how silly I was for thinking I could get this person to talk to me.”
I believe in being self-deprecating. Self-awareness is key in this business; if you’re willing to make yourself look silly and laugh at yourself and have fun with the work, I think people are more willing to listen to you on the occasions you ask them to take you seriously.
Bonus question: Who is the most famous Charlotte Wilder? Any relation to the poet?
Ha, yeah. The playwright Thornton Wilder was a relative somehow, and his sister Charlotte was a poet. She’s who the Wikipedia page for Charlotte Wilder references, which cracks me up, because the last sentence is “Charlotte Wilder suffered a mental breakdown in 1940, the repercussions of which lasted until her death.”
I’m like…yeah, sounds about right. If I ever get my own Wikipedia page I’m going to edit that same line in.
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