This week’s conversation is with Shea Serrano, an author and journalist.
His books include The Rap Year Book, Basketball (and Other Things), and Movies (and Other Things), all three of which were New York Times best-sellers
Two of them were number one on the list and one was picked by Barack Obama as one of his favorite books of the year.
Shea is also known for his work with the sports and pop culture websites, The Ringer and Grantland.
This conversation is as real as it gets.
Shea used to be a teacher and he loved it — but he couldn’t afford to take care of his family. He had to figure out what else he could do and that led him to writing.
Shea’s story is about perseverance.
It’s about outworking the competition so he could provide for those closest to him.
It’s about pushing fear aside and going for it.
In This Episode:
What is he pursuing in life?
Money. Money is like the answer here. That’s not necessarily the main thing, but it’s what I need to get to the main thing. The main thing here is I just want to take care of my people. That’s all it is. I’ve got like a very close group around me, a group of family members around me and I would like to be responsible for them having a better life. That’s been the whole goal with all of this stuff. And it starts out small.
Why is money important to him?
Before I was a writer, I was a teacher. I did this for nine years. I taught at a middle school in South Houston and I loved it.
It was one of those jobs where you start doing it and you go like, oh, this is what I’m supposed to be doing with my life. It was one of those. And then life started to happen for me and for Larami. And you realize, oh, you can take care of a family of four or a family of five on a teacher salary, making 40-something thousand a year, maybe. $1,100 every two week was the paycheck. And I couldn’t do it anymore. Writing was paying me way more than teaching so I had to move over to writing.
How did he get into writing?
I was teaching and Larami was teaching. She got pregnant with the twins. She couldn’t work anymore. All of a sudden, we only had one salary to live on and you realize very quickly these numbers don’t fit. We have too much in the bill column and not enough in the income column. I need to like float us until she can get back to work, about six months later. And she was like, all right, I need to make $400 extra a month. How can I do that? I started applying to work like, can I work at target? Can I work at a grocery store? Can I be a waiter at a different restaurant? And I went on a few interviews and each of the interviews they were like, “Oh, we can’t hire you because you already have a full time job. You can’t work when we need you to work. So this isn’t going to work out.” I’m like, “All right. Well, that fucking sucks.” So I’m at home, Googling work-from-home jobs. Writer was one of them. And I click on it and I’m reading through the list and it was like all you need to be a writer is the internet and a computer and then you can be a writer. There you go. So I said, well, I have both of those things. Let me try to do that.
What gave him the confidence that he could make it as a writer?
Once you get into the rooms, you realize that people who are in there, you sort of build them up in your head. They’re just like these mythic creatures who have some sort of a unnamed talent or skill that you don’t have. And then you get in the rooms and you talk to the people and you realize like, oh, there are definitely people in any industry who are just innately more talented than everybody else but that’s a small, small percentage of the people who make up the writing industry. All of the rest of them, we’re all working with the same skillset. It’s just a matter of, who’s going to knock on the door the loudest? Who’s going to stand there the longest? Who’s going to try the hardest. And once I realized that’s all that this is, this is just like a straight up endurance challenge, oh, I’m fucking good. I can’t run fast, but I could run for a long time. You know what I’m saying? And that’s what it felt like.
How he structures his writing process
It starts out very clearly, this is the point I’m trying to make so every sentence that I write should help me arrive at that point. If it doesn’t help me arrive to that point, then I just delete it and keep moving. I’m just like carving, carving, carving until I get to where I’m trying to go. It’s the same thing with anything that I write. There’s always a central thing that I’m writing my way toward.
What’s the most important step to close the racial divide?
I think a lot of the onus here is going to fall on white people, honestly. And I don’t know if that’s like a sacrifice most of them are willing to make, because the other side of it, we can fuss and make our points known and tell you all of the things. Here’s a sloppy metaphor. If you’ve got like two kids playing and one kid has nine toys and the other one has two toys, ultimately the kid with nine is going to have to decide to give some of the toys away to the other one. That’s where we are I think with things. We are being very loud and very clear about the injustices that are occurring. And now is the time for some of you all to hand over some of your toys
What’s his approach to life?
All I want to do is just make some cool shit with people I like. Professionally, that’s like the whole thing that I want to do. If I meet somebody, “Oh, you’re cool. You want to do a thing?” Professionally, that’s my whole thing. I think outside of that, just like as a general mode of existence, I want to try to do as much stuff as email from the agent and the agent is like, “Nuh, they decided they’re going against it.” And then I get sad because I’ve been working on this thing for three months. And then I go in my bedroom and I lay in the bed for a few minutes. And I look at my phone and I just sort of scroll endlessly and don’t do anything at all but just be sad, for however long that lasts, two hours, three hours, whatever it is. And then I take a breath and then I get out of the bed and then I go find Larami. And then I started talking to her and then I realized we’ll just try another thing. This happened. Well, let’s figure out what the next thing is and you just go do it again. And it’s the same thing with life stuff. A sucky thing happens and you feel bad about it for a bit. And you let it sit with you. And then you’re like, all right, what can I do so that this doesn’t happen again? And usually it’s a very predictable or an easy answer to find. Sometimes it’s not. The stuff that really gets me is the stuff that I can’t control.
Allow yourself to feel emotions
You got to allow yourself that airspace to feel whatever it is you’re feeling because, oftentimes, the emotions that you’re having, even if they’re not correct, they’re usually like not supposed to be correct. They’re just things you’re feeling and you just got to get them out of your body, if that makes sense. And then once they’re out, then you feel better.
What’s the key to success?
It all comes down to grit. A percentage of the people, a small percentage, super talented. You’re never going to catch them. You’re never going to be as good at basketball as Lebron James. But all the rest of them, you got a shot. You got a chance. Just fucking outwork them. That’s what I’m going to keep coming back to. That’s my only trick. That’s my only real skill.
What three words describe him best?
If you ask Twitter to describe me in three words, the three words you’re going to get, shoot your shot, which is like a phrase that we say all of the time. And it’s just like, just try to do the thing you want to do. But that’s been like a running theme for years at this point. I stole it from a student of mine. I mean, not even a student of mine. I stole it from a student at the school when I was teaching. It was like the most inspiring thing that I had ever seen.
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- Finding Mastery 135: Michael Rosenbaum, actor & comedian, on Caring Less What Others Think
- Finding Mastery 095: David Epstein, Bestselling author and investigative reporter, on His Writing Process and How to Tell a Compelling Story
- Finding Mastery 043: Ryan Holiday, Bestselling author, on the Destructiveness of One’s Ego
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