For Part 2 of our Q & A with writer Will Leitch, we got a bit more philosophical. Leitch and I discussed how to get ahead in an industry saturated with writers, but we also discussed the state of modern discourse.
Leitch is known as a fairly centrist figure in a world that is very extreme on each side of an issue. Whether it’s political, sports, or culture, you can trust that Leitch isn’t just going along with the extreme crowd on either side.
Here’s our discussion about being organized, keeping things in perspective, and being ready when the opportunity arises.
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SB: How do you keep up with all of the different publications that you write for?
WL: I’m very very organized. A fundamental thing that nobody realizes that will get you far in life: Just be organized. And if you have a deadline, turn it in on time. The average person is busy as hell all the time and just wants someone to make their job easier. If you make life easier for people then they will want to keep working with you. I turn stuff in early and it’s clean and the changes that they make are minimal and I’m not a diva about them and because of that I’m able to get a lot of opportunities. People want to work with me because I’m not a jerk, I trust my editors, and I turn stuff in on time. To quote Woody Allen again, “90% of life is showing up.” I think I’m an OK writer and I’ve figured out my voice a little bit, but I’m not a genius. I have to hustle and make life easier for people.
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SB: The internet has turned into this world of extremes. It seems like every piece is either extreme to one side or the other. You tend to be one of the few centrist voices left. How do you remove yourself from the vitriol and extremes of the internet to be able to form your own opinions?
WL: One advantage that I have is that I don’t spend a lot of time on Twitter. It’s not because I don’t like Twitter, I actually think it’s great and has a lot of utility. But, I’m not on it all the time. Some people’s entire news source is Twitter. Inevitably, you can’t help but get caught up in the same thought process as everyone else and then everyone compares to each other. I try to remember that everyone in the world is trying and I think it’s helped me get a perspective where I’m able to take a step back and think about where things land in a larger context.
Part of that is an old newspaper mentality. The idea that something is a big story today and tomorrow is birdcage liner. We get caught up in the idea that the thing that is happening right now is the biggest, most important thing that will ever happen. And we tend to focus on that thing and everyone gets riled up and reacts to it so strongly. We literally have a hard time remembering things that happened a week ago.
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SB: What’s it like being a centrist in a world of extremes?
WL: Everybody hates a centrist now. Everybody hates someone that doesn’t take really strong stances on one side or the other. Both sides are wrong by definition. The extremes on every side of every issue are wrong because that’s not actually how the world works. We convince ourselves that’s the way it works because now we only talk to people on our extreme. But that is not actually the way things are. To me, the more important part of things is getting the emotional truth of things correct rather than having some big stance that people would sell in a headline.
You have to not trust yourself in a lot of ways. Everybody has just decided that whatever view they have on something has to be right. I try to be as skeptical of my own views as I am of everybody elses.
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SB: One of the things that bothers me about the internet world, and especially Twitter, is that it seems like everyone is waiting to destroy you. For example, baseball player Torii Hunter just signed with the Minnesota Twins and in his press conference he said something about his dislike of Sabermetrics (advanced baseball stats). Immediately I had four or five people in my Twitter feed bringing up that years ago he also said something negative about homosexuality. To me, those things are so disconnected, but to Twitter they prove that he’s some kind of monster. Personally, I’ve never watched Torii Hunter play because of his religious or political views, nor do I care about his views on Sabermetrics. I watch him because he’s a great hitter and fielder.
WL: The idea that everything is constantly this referendum or this stance on something is wrong. We’ve turned the entire culture of people talking to each other into some sort of weird oppo-political research experiment, where if someone says something that you disagree with, you start looking to see what else they’ve done. It’s so strange, because, of course, I disagree with you on a lot of things, we don’t share a cerebral cortex! There’s been this weird weaponization of disagreement that, while I understand why people find it cathartic, I try to fight against it whenever I can.
We act like we know these people and we don’t. That was the idea of Deadspin from the beginning is that we don’t know these people. There was this hero worship where some were at the top of the mountaintop and others were just terrible and needed to be destroyed. We don’t know anyone at all. We know our family and our loved ones. The idea that we know something about Torii Hunter because he has a problem with gays and said something about Sabermetrics is crazy. Listen, I disagree with him strongly on both points, but I don’t think he’s a monster. I’m sorry, I don’t. I feel like sometimes that gets you in trouble. The idea that someone holding a viewpoint that’s different than yours tells you something profound about them is not how we actually operate in our life. Actual, non-online life, people don’t actually do that. We see people all the time in our daily lives that we disagree with. It happens constantly, It happens when you go to the grocery store. We are not doing this constant judging and bastardization of people with viewpoints different than ours in normal life.
Everything is more complicated than we could ever possibly imagine. The idea that you could somehow capture a human soul in a tweet when you couldn’t capture a human soul in a 90-volume encyclopedia just shows that the format gives the illusion that we understand something and we just don’t.
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SB: Right, and continuing the baseball thing: There are nine guys on the field and I would say none of them totally agree on everything and it doesn’t affect the way they play or the way they interact with each other.
WL: I think people actually know that. Maybe I’m being naïve. Deep down in their hearts people know that, which is why they don’t act like that in the real world. It’s why you don’t see people constantly running up to people and calling them A-holes. People paint it as a courage thing, but I don’t think so. If someone walked around the world speaking the things they are saying online we would think they are a psychopath or a murderer. In the real world we recognize the banality of normalcy. We know the person we are buying our sandwich from, or the person next to us at a ballgame, or the parent of one of my kid’s friends has views about certain things that I personally find abhorrent, but we don’t actually get in fights with those people because that’s not actually how the world works. For me, I try to bring the real world to online interaction, which is not always the easiest thing to do, but I feel like it’s important.
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SB: What’s the biggest factor to keeping that in perspective for you?
WL: I started writing online in 1997. When I was writing online there weren’t that many people online and this internet thing was this amazing place where you could write what you wanted. I remember life without an email address. When I got my first email address you had to go to an internet café and you would write to your friends across the country like you were writing a letter from the front in a war. And you would respond to a person a week later. I feel like that helps my perspective a little bit because I remember when there weren’t that many people writing online and that it was a gift and it would change your life in this very positive way.
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SB: You’ve made a career out of writing and specifically out of your opinions in writing. What’s your main advice for someone who wants to follow in your footsteps?
WL: You have to make sure you want to do it. When AJ and I started The Black Table, each of us had jobs that we did not enjoy. We had to make a decision to commit to this. We said, ‘If we turn out to be 40 (like that was 90 years away) and are failures are we going to keep doing this?’ And we said, ‘Yeah!’
You have to really make the decision to do it no matter what. It’s how you end up answering phones at the doctor’s office when you’re nearly 30, because you want to write. I was so committed to it that I wrote a bunch on the side, I wrote when no one was reading me, and that made me a better writer. It helped get my name out there, and I figured out my own voice. It’s basically muscle memory now. I figured out what I was good at and I figured out what I liked and what my voice was, so that when opportunity did arise, and it took a while, I was ready.
It wasn’t just me who moved to New York to try to make it was a writer in 2000. A ton of us did it, and some of us washed out because they only kind of wanted to do it, or decided they didn’t want to fight for it. Some people said, ‘Screw it, I’m going to Law School.’ And that’s fine, there’s nothing wrong with that.
You don’t know when the opportunity is going to come, if ever. It’s work done in private, it’s work done alone, and it’s work that you have to be your own worst critic. I think that’s the key for any field. You have to know what you want to do, and you have to know that you’re good at it.
For Part 1 of our discussion, click here.