Transcript
Speaker: OACNFers, don't forget, Saturday, October 24th at Gratitude Brewing at 1 p.m., Chuck Klosterman is coming to town for a live recording of the podcast. We'll be talking about his new book, Rock, a mainstream alternative history of alternative mainstream music. And his book, Football, maybe. And writing in voice and style. And he is singular. And you can see him in person.
Speaker: How to do it. ah RSVP with a free ticket at the link in my newsletters, and my Instagram profile, at Creative Nonfiction Podcast. The place will be packed. Secure your free ticket. It's free and open to the public, but securing that ticket gives us a sense of what the headcount's going to be so gratitude doesn't get blindsided by Klosterman fanboys.
Speaker: You don't need to show the ticket. Again, it's just for the head count. Come see us, come join us and have a great time. October 24th, 1 p.m. Gratitude Brewing, Eugene, Oregon. po Well, you know, and it just speaks to the creative process, you know, I mean, it's messy. And, you know, there's times when it's incredibly efficient and perfect and beautiful. And, you know, you're like, OK, I've got it now.
Speaker: But, you know, every time you're starting over.
Speaker: OASian Efforts is the Creative Nonfiction Podcast, a show where I speak to tellers of true tales about the true tales they tell and the art and craft of telling said true stories. I'm Brendan O'Meara with apologies.
Speaker: Today we welcome back Seth Wickersham. You know him as a senior writer for ESPN.com and ESPN the Magazine, RIP, which I believe this podcast appearance is his third trip.
Speaker: He has achieved anthology status. His best work over 26 years at yeah ESPN is in 480 tidy little pages titled Beyond That Hill, stories from the summits of sport with a foreword by his buddy and colleague and master in his own right.
Speaker: Wright Thompson. It's published by Hyperion Avenue. I should add right off the top that I should have in the coming week or two Neiman storyboard annotation of Seth the Mammoth profile on Denver Broncos head coach Sean Payton titled the second season. Well, his feature titled the second season. I don't know what the storyboard annotation is going to look like. i don't know. Talk to Mark.
Speaker: Talk to Mark Armstrong over there. It's a 15,000-word feature that is a stunning piece of work. In any case, pay attention to this space for news on that thing.
Speaker: But yes, Seth is the author of It's Better to Be Feared, his Patriots biography, if you will, for their 20-year dynasty, and American Kings, a biography of the quarterback.
Speaker: And let me be the one to tell you that he is one of the good ones. Just a great person on'm being on top of being a tremendous writer and reporter. I think that comes across in how he speaks, in his generosity of spirit and willingness to share his vast experience with you.
Speaker: I mean, take these blurbs, for instance, from Jonathan Eig, Pulitzer Prize winner. Wickersham stands with Plimpton and Halberstam among the finest sports chroniclers.
Speaker: Okay, she chew on that one for a bit. And then Peter King, longtime Sports Illustrated writer. Wickersham's terrific prose and storytelling are buttressed by his tireless and insightful reporting.
Speaker: Damn. Show notes to this episode more at brendanamero.com. Hey, okay, listen, here's why you want to visit the show notes. I don't know who does. I don't look at analytics. I have links to past episodes that I think you'll enjoy based on the current one. So yeah maybe if that rhymes with this one, that way you're like, oh, cool. I like this one. So maybe I'll try this. It's my own algorithm, if you will.
Speaker: I also have links to 500, 400, 300, 200, and 100 episodes ago. so you can just get a taste of the full bounty of the backlog without having to go hunting. Though you very well can hunt if you'd like.
Speaker: And you can always subscribe to please actually subscribe. I'm begging you to subscribe to the monthly newsletters. Of course, there's Pitch Club. If you want to get better at selling stories at welcome to pitchclub.substack.com or the embed form in my website. And the Rage Against the Algorithm if you want to rage and get some cool recommendations.
Speaker: There's always becoming a patron over at patreon.com slash cnfpod to throw a few dollar bills into the kitty to help keep the lights on here. You know, I don't take ad revenue, so this is a listener supported. Very punk rock. Very metal.
Speaker: And if you don't want to part with that sweet, sweet burrito money and don't I know, leaving reviews and ratings for the podcast or the frontrunner, Or Six Weeks Saratoga, too.
Speaker: They're free and take you less time than you think, and the additive effect of all those is worth more than money in a lot of ways. But we like money, too. What a treat. What a ride you're in for with Seth here. His work can be found at ESPN.com, and you can visit his website, SethWickersham.com, and click around. It's worth it.
Speaker: It's worth the browse. And follow him on Instagram at Seth.Wickersham. In this episode, we talk about, did I just vocal fry? God damn it. That's not cool.
Speaker: I hate that. I hate that fry. i'm so sorry. In this episode, we talk about, yeah, there you go, from the gut B.O., getting beyond access porn for his patent profile, having an idea of where you want to end a story, the messy creative process, each time you're starting over, shades of grayness, not being dissuaded by lack of access, lucky that people were invested in his success from the start, breaking through creative plateaus, the benefit of being a young writer, oh, that naivete,
Speaker: Everything in a story is a reflection of you. Needing a crew, that was a cool part of this. How your writing voice can adapt, that's also a very cool part of this. And the notes he has taped to his computer.
Speaker: You might want to pair this episode with Pamela Koloff's appearance, Tony Rahagen, and Justin Heckert's. I'm blanking on the episode numbers, but that'll be in the show notes. See, there you go. Go to the show notes. Parting shot on the struggle of embracing my own path, even all these years later, when I like the paths of others so much better.
Speaker: Grass is always greener, am I right? But it's high time we hear from a modern master in Seth Wickersham. Thanks for coming back, man. Here we go. Am
Speaker: I allowed to swear, by the way? Oh, yes. Oh, okay. Are you just fucking insane? Just kind of a sloppy person. No, I'm still such a fuck up. I'm going to be a fuck up probably for the rest of my life. but This is going to have to interest somebody somewhere other than me.
Speaker: So you're so deeply embedded with Peyton and the Broncos for those weeks. And then, you know, you're getting all that material, filling up your recorder, filling up your notebook, all this stuff. and So when you come up for air, what what are the first steps that you're doing when you're out out from the maelstrom that was that time?
Speaker: Yeah, you know, it was sort of like, um you know, you had to get your feet back under you, you know, because I had really been disconnected from my life, from my family's life or for 15 days. um You know, i I was in Denver that long, but it wasn't like I was driving around Denver. I wasn't hiking in the mountains. Like I was at the facility all day and all night. And so it was a very limited existence.
Speaker: And, you know, so I think that like after i got home and started to sort through things, you know First of all, I think that there was always a question of like, do you know do we try to do this quickly? And once I think the editors were like, look, this is a special story.
Speaker: Broncos aren't in the Super Bowl. There's no reason to get it out. arbitrarily quickly. So yeah let's make sure that we do, you know, right by this material. um i think that like doing two books helped me quite a bit because I could have done a book on this. I mean, I never really thought about it, but I could have, I had enough material to do that.
Speaker: And, you know, I easily could have written the story, you know, five times longer and that would have been a book, but yeah, I think that like, and you know this too, but when you're doing a book, you're just, the challenge with doing a book in a lot of ways is not just getting new reporting, it's keeping everything straight in your head. And we all have different methods that we have of doing that. But having done a couple books helped me do it for that story because
Speaker: I was sort of in good shape you know of you know being able to keep um you know a lot of moving parts in my head at the same time and to think about how to deploy them best in service of the story I was trying to tell. So that's kind of what I did. And you know it took a while to do.
Speaker: And then you know I really started writing and I wrote it like I would write a book. you know, a thousand words a day. And I really tried to think best about, you know, you have a natural arc with that story in the sense that you were embedded with them for the playoffs, but I didn't want to tell it every day for two weeks. I didn't want that to be the structure of the piece. And so when i actually got to writing it, I had kind of an interesting structure that I decided to do for it.
Speaker: And, you know, I wanted to see how that felt and it ended up feeling pretty good. How did you arrive at this structure? Well, so football teams are very scheduled and regimented and, you know, they're all about routine. And so I didn't want the reader to be thinking, okay, here we are another meeting. You know, this is the 1030 full staff meeting on a Tuesday. You know, I didn't want readers to feel bored by the routine. And so what you know What I decided to do was ostensibly tell it as the arc of the story leading up to the AFC Championship game, Monday, Tuesday, Wednesday, Thursday, Friday, Saturday, Sunday, with a big deviation in the middle of it when i tell the story of the Buffalo week the week before. And I didn't do that Monday, Tuesday, Wednesday, Thursday. I kind of took the best stuff of that week
Speaker: the stuff that I thought was the most interesting, the stuff that I thought added to the story I was trying to tell the best. And then I picked up and finished that AFC Championship game week. And so I guess it was a little risky in terms of how I told it, but I think it felt right and hopefully it resonated well.
Speaker: Oh, for sure. it's a It was great to get um get a sense of that. you know part Part one kind of sets up those and sets up the the stakes in that way and also just the the timber and the mood because he obviously loses his starting quarterback on the cusp of the Super Bowl. Uh, but then, yeah, then you kind of backtrack to do some of that more biographical stuff, uh, in that part. But then there are all these grace notes that harken back to part one, but then foreshadow part three. So there's a lot of moving parts that you're working with. And you talked about a moment ago, just the method of like keeping it all straight, be it for a book or a magazine piece. But given that there are all those elements, how did you keep all that stuff straight?
Speaker: I mean, what I did was I printed up all my notes and I had them bound. So I kind of had uncle a bound book of my notes. Like a bound chronology too. Yeah. And it was several hundred pages. And, you know, I just went through it and I highlighted things that I wanted to use, you know,
Speaker: I picked the best things that happened on Monday and I wrote to them and then I ended up cutting some things later, whatever it was. But I knew that there were moments and I almost kind of going through my notes, I noticed them in real time when I'd star things where i knew something important had happened. Now, what it meant in the big scheme of things, I didn't quite know.
Speaker: But that's where, you know, the benefit of having time on the back end helps because, you can think about what matters and what doesn't and how best to deploy that reporting and how best to set it up and kind of you know have a story that, number one, isn't just access porn. It's not just showing off that I was there.
Speaker: you know You're telling a story and it's about this one person trying to do something interesting. And you know then you have all these little microlarks in it that hopefully add to the picture you're trying to tell. And so you know i don't think that there's anything magical. I know all those people, you know people have all kinds of different methods for how they organize an outline, if they organize an outline.
Speaker: And with that story, I kind of knew what I was writing to for better, you know, and so I kind of felt like I always had some creative momentum behind me. Like Chris Jones, one of my friends, you know, he writes endings first and I've never been, I've been,
Speaker: you know, there was that explosion of all these kind of long form websites and message boards. I want to say like 06 of 708, something like that. It was very fashionable gang gray. And um people would talk about their process and Jones always kind of wrote endings first and then, you know, wrote to that. And even though I don't do that, I think that like there was a lot of virtue in that because, know,
Speaker: You know, my buddy Tom Junot says, if you have an ending, you have a story. And so knowing how you think you want to end the story is really important because then you can, you know where you're going.
Speaker: You know, you can take detours, but you have an end point. And I think that that's especially, no matter what story you're doing, but especially with these kind of complicated multi-thousand word stories that have all of these different themes in them, that is really, really vital.
Speaker: Writing an ending first, I feel, would, um yeah, to each his own with that practice. But maybe sometimes I can, like, paint you in a corner. But I do find that when the ending materializes, no matter where you are, and it feels, like, resonant, like, oh, that's going to be in tune. like Then drop it there because then it's like a lighthouse in the distance. And then suddenly you're like, oh, you're rowing towards this thing. And that's exactly what you were saying. is Then everything every word feels in service of that destination.
Speaker: sorry. Absolutely. and And again, you don't have to end it that way. It's to have an idea of how you want to end it yeah And you can write it up or you can kind of thematically know what how it is you want to end, however it is. But I think that like that's really important.
Speaker: And I think it's more important than, well, for me or for me at least, than, you know, the writing for story types who outline everything to the T. Because I think you can, be you know, sometimes you can maybe be a little bit too wed to your outline,
Speaker: But if you know your destination, then you can color outside the lines a little bit until you get there. Yeah. Yeah. I was helping a friend with a flash essay the other day, and it's an essay that he had wrote, you know, years ago and submitted it a bunch of times and, you know, it rejected for one reason or another. And he's he's had it for so long. And you talk about like kind coloring outside the lines, like the stencil of this particular essay was just, you know, you write it and rewrite it so many times that it kind of ossifies in your own mind, and your own reading of it. And then I came into it I'm like, oh, this first section, they're like I would just delete this first section. And ah it it didn't dawn on him to maybe experiment with that. And then you'll he'll be cutting 250 words and it'll be 700 words instead of 950. And then now the stakes are a little bit different. And it's like sometimes you just need those fresh eyes to just shake it up and be like, no, let's you know let's kill this whole part and see if that, like a hot air balloon, like losing that weight, see if you can gain more altitude. Yeah.
Speaker: Well, you know, and it just speaks to the creative process, you know, I mean, it's messy and, you know, there's times when it's incredibly efficient and perfect and beautiful and, you know, you're like, okay, I've got it now.
Speaker: But, you know, every time you're starting over and, you know, there you have your experience to help you as a bit of a tailwind, but,
Speaker: It's not going to get it done for you and it's not going to make sure that it it accomplishes all the things you want to accomplish. it's It's hard and it's hard each time out, whether you're writing a column off of a game or a political event or long form feature or a book or something in between, whatever it is, um each time you're starting over.
Speaker: Yeah, you you write that in the in the introduction ah to Beyond That Hill. like The next piece is always a bracing reset and like nothing yeah and nothing carries over. And I'm finding that to be true, too, just trying to get altitude on another book. i'm like i I feel out of practice. I'm like, oh, my God, I like i forgot how to write. like I don't know how to do this anymore.
Speaker: ah Ray Thompson and I were talking about it because he did this big story on on Steve Kerr. And, you know, he he thought it came out um earlier this this spring. And, you know, he thought it was his he thinks it's his best profile ever. And, you know, there's a lot of great ones to choose from.
Speaker: But, you know, he spent a lot of time with Steve Kerr in a lot of different states and, you know, to the point where it wasn't stressful to get time with him.
Speaker: Then you know he moves on to the next one on Wemby and you know it's like he can't get anything going with this. and It's like, you know hey, look, I've got, you know he's probably like, you know I've got all of these stories that I've done over the years, some pretty big names in there that you know have trusted letting me into their circle and writing what I see. And then you're just kind of running into this brick wall And so that part of it is is particularly humbling. I know exactly how it feels. you know There was a story that I was looking to get going on on the heels of the Sean Payton story, and it's not going to happen for the time being. Now, sometimes you just keep doing it anyway. But there's some that you're like, hey, look, I think that you need and a level of cooperation to try to do this the way you want to do it.
Speaker: With other stories, you can be completely undeterred and still write a story that checks all the boxes that you want to check and give you a lot of confidence as a reporter, by the way, that you don't need cooperation. But, you know, some of them you kind of do like, you know, like we said, just because you do one and it turns out well, it buys you nothing for the next one.
Speaker: Yeah. Well, that degree of cooperation is so like hard these days. Gideon Nathan's amazing book, Changeover, about um ah Carlos Alcarez and Yannick Sinner. like He didn't really have access to them outside of press conferences. So he wrote the book almost like an art critic. would write about their performance. And it was his, in a way, his workaround with the access he wasn't getting. And nowadays with social media being the way it is and prominent athletes, they have, they're always doing their own some somewhat sanitized docuseries or little micro documentaries on social media or doing full blown ones on Netflix. yeah And they're like, why would I talk to a reporter? And it's like, it must how are you navigating this landscape now of trying to get access to people? out The more prominent, the harder really in a lot of ways.
Speaker: Well, okay, so first I have the blessing of having a full-time job. So for instance, I did a story on Andrew Luck years ago and it was, you know, I had reached out to Andrew in 2019 months after he retired and I wrote him what I thought was a pretty good letter explaining, you know, what I wanted to learn from him.
Speaker: And he wrote back and he said, you know, now's not the time. There might be so a time in the future, but now's not it. And, you know, i stayed in touch with him periodically. Finally, I think 2022 came around and, you know, i ended up spending a lot of the year with him and writing, you know, what was one of my best stories.
Speaker: But there was no guarantee that that was going to happen. And if i didn't have yeah ESPN paying me and I was working on other things or whatever might be, If I had to put all my eggs into the Andrew Luck basket, I would have been in trouble. And so I think that there's that. But I also think that I don't approach it that differently than I did when we had a print magazine or you know before social media.
Speaker: if anything, I kind of like that athletes or famous people have their own social media outlets to talk about things because it just gives you more material.
Speaker: And when I was doing my book on the New England Patriots, you know, I didn't have on the record cooperation from Belichick or, Tom Brady.
Speaker: And one of the best books that helped me was a book that a writer at the Boston Globe did called Fridays with Bill. And Belichick had had this thing where he on Fridays before games, he was often really relaxed and kind of at peace. The game plan was well in motion.
Speaker: And, you know, the media crowd had dissipated to a certain extent by the end of the week. And he could be really expansive and interesting and insightful on an array of topics.
Speaker: And someone realized this, and I wish I could remember the guy's name, but then he basically just put together a compilation. He organized things that Bill had gone long on and organized it and put out a book called Fridays with Bill. And I found that so helpful when I did my Patriots book, just because it was 200 some page transcript of Belichick's most interesting, insightful comment comments on everything from, you know, blocking punts to Tom Brady, whatever it might be. And it again, that stuff just helps in inform what it is you're trying to say and the character that you're trying to paint. um My old boss at ESPN Magazine, Gary Honig,
Speaker: used to say, you know, any piece of reporting works in a story depending on how you think about it. And when he said it, I was in my, you know, early twenty s mid twenty s just starting my career. And I couldn't wrap my head around that, you know, but I think now I understand what he was getting at.
Speaker: you know The more shades of nuance and gray that you can add to a portrait a person, I think the richer the story becomes. When people do their own social media posts or they appear on podcasts with their friends, whatever it is, you know they're drawing upon pieces of their of their personality. And the more raw material you can have of someone's thoughts,
Speaker: the better it helps anything you're doing. You have to do your own work. You have to like meld it with your own reporting in a book. But you know that is it's just invaluable to just have the the raw access to what people thought at a particular moment of time.
Speaker: Because even if you have you know, war and peace access to your subject, you you can't ask every single question. You just can't do it.
Speaker: you But, you know, again, the people who've been out in the public eye, they reveal themselves. And you can, and most people don't notice it. You know, most of the readers of the book won't notice it or won't remember it or won't think about it like you did. And so even if you have information that's been out there, if you can think about it differently in a book,
Speaker: it becomes new and it becomes part of the story that you're trying to tell, which ah ultimately is what makes it your book and not anybody else's. Absolutely. Yeah. That degree of interpretation. And as ah my editor for the front runner would say, like you have your thumb on the scale of this story. Like what you decide to tell is your point of view and why. And you need to be very ah discreet about ah why this matters to the reader. And that's up to you. Maybe someone else interpreting the story and the material differently would write it differently and point to something else along the road.
Speaker: But because this is your thumb on this particular scale, you get to interpret it. And even in my conversation with ah Pam Koloff a few weeks ago, this idea of... The great Pam Koloff. Oh my gosh. the bet She is, my gosh, great the best of the best, right?
Speaker: And ah the degree to which she, um the Skip Hollingsworth method of like kind of throwing away the quotes and writing your way through the quotes. Yeah, That's really, I thought that was really astute. How are you thinking of that? Especially from an investigative reporter, you know what I mean? Where it's like you you can't, obviously there's checks and balances with their process and our process, whatever it is, but you can't stray too far as an investigative reporter, you know? And, um you know, that's the blessing and the curse of investigative reporting is that like, you can imagine, i'm not saying make things up, but you can imagine scenarios
Speaker: and use them to test theories or bounce facts off of whatever it is. But you know you have you're somewhat limited. And so I think that like, but in the same sense, it's your story and and your voice needs to come through in it and you need to tell the story that reflects your curiosity, whatever it is.
Speaker: And so I think that not having quotes or not staring at the quotes and constantly checking for you know for them you know, I think there's a lot of virtue in that method. It's, yeah it's somewhat messy because you um you know, are constantly kind of going back and forth. I've tried doing stuff like that.
Speaker: You know, at the end of the day, I think that like what works best for me is just trying to internalize all of the information so that when I tell it, I'm telling it through whatever storytelling voice I have.
Speaker: And then, you know, on the page I can, improve it, cut it, tweak it whatever it might be, eliminate it altogether if it's not working. But like, I find that, and this is a cousin of of that Skip Hollingsworth method. It's not exactly the same, but I think that like you, if you're constantly staring at notes and putting quotes in or whatever it is, you lose your creative momentum. And so, you know, can you hang on to that can you ride that wave as long as it goes?
Speaker: And then later go back and, you know, verify pure accuracy, make sure things are correct in every way. But it's, um you know, again, that it's that creative process. It's, there's different methods that work for everybody else. And I think that like, as you do this type of creative long form narrative, nonfiction writing, you know, figuring out the process that works best for you is, is one of the,
Speaker: the best things you can do to give yourself a chance to like, you know, tell those stories in the way that you want to tell them. But there's just a lot of experimentation that takes place between now and then, because when you're starting out, you don't know what works best.
Speaker: Yeah, and sometimes with the ambitious stories of which that that you've been known for and write among others, getting those repetitions to write these kind of stories is is very, it's hard, it's labor intensive, it's money intensive too if you're like kind of in the freelance realm, to get those repetitions. Yeah, just to get as many at bats as possible to do this, because that's part of the that's part of the secret sauce, too, is like getting good at this means you got just got to do it a lot. And it's hard to do it a lot, in especially in this yeah media ecosystem.
Speaker: You know, I think that like that's where, you know, our group at ESPN is, again, just kind of fortunate to be in the place that we are where, you know, they'll put a ton of resources behind stories. They'll say, hey,
Speaker: we're going to send Seth to Denver for two weeks straight and send him there a handful of times before that, just to like kind of learn what's going on. So that when I was there for the real thing, it wasn't like I was in those meetings for the first time I was hitting the ground running. And so, you know, that was all in service of a written story.
Speaker: You know, what happens with our investigative stories, it happens with our profiles, other enterprise types of things. But you know, that is where we're really lucky where,
Speaker: We have bosses that really care about this work to the bottom of their soul. And ah write about it a little bit in the in the anthology, but it's like, I'm so lucky in the sense that like my entire career, I've had people who were invested in my success and invested in me developing. And I mean, man, that is, I think I knew it as a young, you know, when I was first hired at ESPN Magazine, it felt like I was in graduate school.
Speaker: you know I was learning from these great professors and getting a chance to write. And you know it was like, I felt like I had won the lottery. And then you know as i became you know a better writer and started to learn about all the things that I didn't know how to do well, that weren't even on my radar at the beginning of my career, I had editors who helped me try to achieve those things, those whatever those elements might be um that I wanted in in my stories. and you know I wanted to add new clubs to my bag and hit higher levels, whatever it was.
Speaker: When you're trying to talk about, you know, all of the elements that make a great magazine story, those were the things I was shooting for. And I've always had people who helped me accomplish my goals.
Speaker: And that is that, like I said, to borrow a phrase from before, i mean, that is a blessing beyond belief. Yeah. When I love when ah Dan Patrick asks NFL players, you know, what was their welcome to the NFL moments? Usually they're getting drilled over the middle or something, something of that nature. But as you're starting at yeah ESPN and you're, you've, you got this ambition to write these kinds of stories from, of the writers that inspired you. um What was your kind of like welcome to a long form moment where you realize, Oh my gosh, like I thought it was this, but it ended up being like so much more or whatever.
Speaker: Well, I don't know. It's a good question. i think that like I had stories that felt like breakthroughs, you know what I mean? And like, you know, early in my career, i did a story on Drew Brees and LaDainian Tomlinson when they were both at the Chargers.
Speaker: And, you know, that felt like in my, of my first few years at the magazine, that felt like, you know, a story that I did where I'm like, okay, that, I can say that that one showed some evolution for me as a storyteller reporting, whatever. And then, you know, there's all these other ones that come up along the way, ah you know, writing about a fire and some of these are in the anthology. Some, you know, writing about a fired college basketball coach as he is on the street trying to find his next job, um writing about a ah mostly gay rugby team, the San Francisco Fog in California and how that
Speaker: dynamic works. um It was very novel, you know, at the time. And then, you know, writing about, we will rock you the most played stadium anthem ever and why, and why we even have stadium anthems, all this shit, you know, then, and then i and then there's moments like, you know, a Tom Brady story I did in 2013,
Speaker: the Bill Walsh book story I did that same year, those felt like big creative evolutions for me. And then finally, those stories set up some of my better profiles like Y.E. Tittle, Andrew Luck, Alex Honnold, those types of guys. And then the investigative part of my career where I started working with Don Van Nade, you know, who's a phenomenal reporter, not just a phenomenal sports reporter, but just a phenomenal reporter. And that we first teamed up 2015, over the the in the time since. I mean, we've done some
Speaker: some big hardhitting stories on the NFL, on the NFL Players Association, on owners, on the league office itself. And um learning from him and doing those stories with him, you know, have, you know, that was ah another huge, huge evolution in my career.
Speaker: And, you know, I'm just lucky because it's, again, it's like, not everybody has those chances. You know what I mean? It's like, yeah I was lucky that I wasn't trying to tread water during those years, but instead I was kind of excelling and given the space and the time the in the repertorial and creative freedom to really go and try to get really complicated, high degree of difficulty stories.
Speaker: Yeah, like in the in the Bill Walsh piece, and you're writing about this book, Finding the Winning Edge, and there's there's a moment, too, in sort of the italicized part where you're kind of tracking this other coach who's like learning at the foot of this. And um it was a – I forget. It might have been the McDermott coach. um But he was – He was ah reading the book because he know he wanted to know what it took to be elite and thinking elite. And I made a note there, too, because in you're alluding to it by like working with Don, ah yeah among others, that ah there is a measure of what it takes to be elite in long form in magazine writing and to be ah ah an elite reporter. So what were some of those ah things as you were looking to like keep leveling up your game, break through your creative plateaus to ah to just become better and better and be thinking in those terms?
Speaker: Well, I think there's a couple things. I think that, you know, one of our editors at yeah ESPN a decade, more than a decade ago, I remember his name is Gary Belsky and he was editing Steve Wolf, the great baseball writer, and he was an editor at yeah ESPN.
Speaker: And he was like, you know, Editing Steve is hard because he's such a tight writer and his thought process in his pieces is so well woven that you can't really edit him. so you can You can tinker, but like you know if you pull something out, you're unraveling the sweater.
Speaker: And I remember thinking, like you know can can I do a story that's that creatively tight? Forget about like not wordy. you know, that's, you know, this is something different. And it's, you know, having a thought process throughout a piece, even if it's through the person you're profiling.
Speaker: So that like, you know, if it's not working, it's not going to be solved by tinkering. You have to start over. And, you know, I think that like that was something that I really wanted to try to do. It's just kind of like have a so a story that the process of reading it was that kind ah kind of an ozone element to the story. it was it was It was an experience just to read it, forget about the facts and what happens in it.
Speaker: But the the storytelling experience was part of it. So I think that that was part of it. That was one thing I was definitely trying to do. And then I think that like being in college with the friends that I had, Wright Thompson, Justin Hecker,
Speaker: and there's more, Robert Sanchez, you know, has done great work. He was a friend of mine from college. You know, reading what they've done and their ambition over the past 25 years has been really helpful to me too, because we're not competitive in the strict sense of things. But it's like, I think that we keep each other driving to the rim, you know what I mean? And not stopping short. And so I think that like that helps you because you see things that your friends do in stories that, you know,
Speaker: you're like, you know, that's something I need to work on. And, you know, it could be a piece of analysis. It could be getting out of the way when you have, you know, witnessing a phenomenal scene in a story and not stepping on it.
Speaker: It could be use of first person or use of second person, all these different elements to it. But I think that like that has been helpful also. Like Justin Hackard wrote a terrific story on Eli Drinkwitz, the Missouri football coach, want to say two years ago.
Speaker: And he wrote about him kind of being a nerd and wrote about him through the perspective of him wearing glasses. And I thought that what a fascinating thing to do And, you know, Justin was the only one smart enough to think about it and to see that, like, all of the material you can play with and all of the ways you can see someone's life within the context of being nerdy in a profession where we kind of glorify
Speaker: to be blunt, like a lot of glorified gym teachers. And so, you know, again, it's like thinking about those types of things and then, you know, trying to figure out a way to apply them to your own work, I think has been, again, something that in the course of my career, like I don't think I'd have a collection coming out if not for the people I went to college with, the people I worked with at ESPN, the people that I've worked with, you know, the past 10 or so years at ESPN,
Speaker: A collection's funny, it's a very singular celebration. But really there's like such a group of people that go into helping you accomplish something like that, that it feels like a little um foreign and incomplete to take too much credit for it. Does that make sense? Oh, yeah. Well, you write right at the start, like a published collection is massive ego trip. And if I'm being honest, kind of absurd. And i you're you're kind of talking to the absurdity of it, that it is it does feel singular as it should. You deserve that. But yes, there is this village and ah maybe even a metropolis that brought it to into fruition.
Speaker: And, you know, i i include, you know, some of the stories I have double bylines on, you know, with with Van Nata in the book, because like, number one, those are some of the stories that I'm proudest of. But number two, you just can't,
Speaker: do a collection like that, it would just be incomplete without it. And so I'm very wired to look ahead to the next thing. Like I never go back and read my old stories. By the time a story goes out in the world, I've read it so many times that like, I really you don't need to go back and read it. And then life takes over and you, you know, months pass and then years pass and then more, you know, you're just not,
Speaker: you know, there's just the reality of life in the job isn't such that you don't go back and have a ton of time to reread your old stories and see what you did. But I had to do it for this project. yeah I didn't re reread every single one, but like, you know, I picked 50 of my best stories of all different lengths. You know, so some of them i wanted to be shorter. i didn't want every story in there to be a long profile or a long feature. I wanted, you know, some of my best writing I thought was on shorter pieces. And so When I went back, you know, when you're forced to do that, it's really cool because you remember who you were back then and maybe where you were and all of these, these, these memories and influences and things that were happening at the time come back to you and you realize just how much went into, you know, that particular story and all of you
Speaker: people who helped. And it's very humbling. And I don't mean that falsely. It's just, it's incredibly humbling um because you realize just, you know, how many people assisted you along the way and how differently things might've turned out if they hadn't.
Speaker: Well, yeah, this notion of you know revisiting pieces that you you might have written 20 years ago or something, and now you're like 20 years more developed as a writer and a reporter and everything. And I wonder if if they you came across stories that you're like, oh, I kind of wish I had another crack at that one.
Speaker: Yes. There's a couple that I um you know look back on in my career that like I wish I had a little bit more wisdom you know to tell that story because you know it maybe could have just been something bigger. And you know some of that was, most of it was where I was at in my career.
Speaker: Some of it was you know writing for a physical magazine and stories have word counts. And you know especially the first 10 or so years of my career, it was hard at ESPN to get more than 3,600 words for a story. And so I became really good at writing 3,600 word story, but there's a big difference between writing a 3,600 word one and 4,500 word one and a 5,000 or And then like,
Speaker: you go beyond that sometimes and so i think that like some of the constraints of the magazine, you know, were a factor in that, but, you know, most of it was, was me and just, you know, what the, you know, the perspective that I had at that time, there's a lot of benefits to being a young writer.
Speaker: You know, you don't have, You know, you you can see things and find things super cool because you just, you're you haven't gotten that weathered.
Speaker: And, you know, as you get older, you know, a lot of the perspective ends up coming through in the story. But as a young writer, you know, you, you know, sometimes the lack of that is what makes the story super cool at that moment in time. And so there's the yin and yang with that. But like, yeah I did a story on Broderick Thomas that's not in the collection.
Speaker: i want to say 2015. He was a football player. And it was really like one of the first stories about, know, their bodies and even minds breaking down without the game. And you know that would is that's one I'd love to have another you know pass at, just thinking off the top of my head, because like I think that like if I encountered that material now, I would be able to do a lot more with it. And I love when you're bringing up um Justin's piece and his observation the coach for that nerdy point of view. yeah and I think that really gets to ah gets to voice. And what we're oftentimes with voice, we're cued into like pyrotechnical language or just ah someone's sensibility in terms of vocabulary and how they deliver sentences. But I think voice can be every bit is just what you notice too, right? Yeah. Everything in a story is a reflection of you.
Speaker: ah You know, it ends up being, you know, your line of questioning to what you observe and what you put in, you know, it's a reflection of the things that you see. And it's one of the reasons why you could send Tom Juneau to write about Aaron Rodgers and Tim Kuhn to write about Aaron Rodgers. And both stories would be awesome. And they might be completely different because they're just two different people who are so smart in terms of their observations and their style and their thoughts.
Speaker: But they're all you know, both of them have the the the confidence to see him through their eyes. And so, yeah, you know, I mean, and and Justin's so good at it. You know he's just always been, even when we were back in college at the Missourian, you know, his eye for detail and observation um was always there.
Speaker: And it was really... um Again, you're in college with these guys. And so that's just your college experience. Like, you don't know it better. And there was a part of us that's like, yeah, we're we're going to go places. We're going to be ah you know we're going to do some stuff in this profession.
Speaker: but you know, you don't know how and you don't know for sure that you're going to do it. You know, we just kind of carried ourselves like we did, but it's been, so God, it's just, it's it's a miracle that like all of us are thriving in our writing careers. And, you know, i can be proud of Justin's work or Wright's work or Robert's work or Tony Rehagen's work, whatever it is, because I know where it started.
Speaker: You know, I think that like, I really feel bad, you know, writing is such a lonely job and I feel bad for people who don't have a crew. Like, I think you really have to have a crew. i had a college crew.
Speaker: First couple years at ESPN, there was a bunch of us who were kind of young writers and very ambitious, you know, that was a crew. And then we have our group now of people who are on various text threads or, you know, Kevin Van Valkenburg, Tom Juneau.
Speaker: But, you know, you need, you need kind of a band, I think, to always kind of, know where your head is at any given time so they can help you tap into those things when you're doing your work.
Speaker: Yeah. Well, they, is speaking of like having a band and beyond that hill being such a formative lyric of Springsteen and the E street band, I mean, you talk about his big band and having that crew. I mean, he doesn't become the boss. He doesn't become who he is without that crew. And I think you've been echoing a lot of that sentiment in this conversation.
Speaker: Yeah, I mean, he's talked a lot about it. You know, he's very proud that he was signed as a solo artist. You know, he was signed as one of these next Dylons by Columbia Records, I think in 1972. But he never he you know, he was on the record label for 10 years before he released a solo album. i mean, they were all band albums.
Speaker: And he he knew that he could get to a certain place alone. but He couldn't get where he wanted without all of those people taking his ideas and giving them life and making them bigger than he could have done. And in my own way, I get it.
Speaker: I mean, you know, my career changed when I started working with Eric Neal at ESPN. He had been a friend. i never really had worked with him. he was ah He wrote a lot and he became an editor. And I, you know, he was someone who you can't get better unless you're working with people who are better than you.
Speaker: And he's somebody who is whose insight has just helped me in value in so many ways because he He knows what I'm going for and he tries to help in a sincere and earnest way to help me get there. And you have no chance, you know, without someone like that in your life. i mean, you really, you can get somewhere, you can get to a certain level on your own, but you can't really get to, i think the best level without being challenged by people and
Speaker: You know, again, i can send, I can call right and have called right at any hour trying to walk through a reporting problem or a writing problem or a storytelling problem, whatever it is, you know, Tom, ju know you know, know what I mean? All these guys think in magazine terms. And so they speak the language that you're aspiring for. And so they can help you in a way that, um you know, again, it's like, how do, how do you, i would hate to think of where my career would be without all these people.
Speaker: Yeah. Well, there's a moment you write about in the introduction where you're like, like, how will I do this? Can I do this? Yeah. And that really speaks to the doubt inherent in this. So when you've been confronted with that inevitable self-doubt, be it through the reporting or the writing. Yeah. How have you managed to not put it, put it at bay, but maybe dance with it in a way that you persevere through it Well, you have to do it.
Speaker: you know Whether you you know you can do it or not um is a question you have, but it can't be the overriding question. i mean I think that like there's some things I have taped to my computer that you know kind of the kind of help me.
Speaker: let me see here. This was from Tom Junot, and I don't remember where he got it. I don't think this is his. He got it from someone, but I thought it was really helpful. He said, first, so this is about the draft process. First, get the story down.
Speaker: Second draft, improve the prose. Third draft, get the story to tell you what it means. Because I think we always think like, hey, what does this mean at the beginning? You can be weighed down by that and you can be wrong. you know And so I think that like that liberates you to just tell the story and figure out what it means later. um Don't be deceived by life outs by life's outcomes. That's a line from a Michael Lewis speech that he gave at Princeton um where he talked about the role of luck. And, you know, I think that like we all have a story we tell ourselves. I did this book on quarterbacks because I worked hard and, you know, that's what made it unique and all these things. And there's an element of hard work.
Speaker: that's essential to any good product, but a lot of people work hard. You know my mom was a special ed teacher, she grinded. And so, you know, I think that like, you you have to acknowledge that there's some luck in your career, I think, and it helps you. um This is Springsteen, more than rich, more than famous, more than happy, I wanted to be great.
Speaker: I feel that, I still do. This is from John Harbaugh, who I have no particular affinity for, but I think during the after the pandemic, I think he he had this slogan for his team, nobody cares, work harder.
Speaker: You know, at the end of day really nobody does care. Like you got to grind through it. um This is from my dad, Kirk. Worry is optional. The only thing that makes a difference is action.
Speaker: That's obviously, can I do this? That's how you answer it. You answer it by going. And then this by Eric Neal, we got this. You know, it's very simple, but he always kind of approaches things with that affirmation, it is going to work out and we're going to be proud of this. And that's where a little bit of weathering helps you because you can understand that perspective. Whereas maybe at 25, you didn't have enough reps to maybe understand that these things work out.
Speaker: Yeah, i love you ah writing and giving voice to this idea. You say, my but my biggest professional fear has always been that I will plateau. And i when I hear all those quotes that you're reading, i i i read those as like, oh this is a good these are these are good mantras, if you will, to break through plateau and to make sure you don't get complacent either.
Speaker: Yeah, well, so years ago we had this party um and we invited Gary Smith and Tom Junot to come to it. And I didn't know Tom, was first time I met Tom and I didn't really know Gary. It was the first, but you know, they came and they talked about some of their stories and it was really, it was unbelievably helpful. But Gary was kind of, it was also interesting because you have these two great writers, like phenomenal all time writers who are very different people and have very different jobs.
Speaker: Gary was at the end of his career at Sports Illustrated, and he, at the end of his career, had these requirements for each of his stories. where he wanted to have full access to the participant to the main subject, full access to their family, and then the ability to ask follow-up questions in a, maybe in person over the phone, whatever that is. And that's a's it's a great structure for a story.
Speaker: um But he you know he was like, I write four stories a year and they have to all check these boxes for it to be worth it for me. And then you had Tom on the other hand,
Speaker: who, you know, some of the stories he does are his ideas. Some of them are David Granger's or whoever might be at Esquire at the time, but he's got to go do them get it the fuck done. And nobody cares. Just get us a story. We need we need it for this issue and get it done.
Speaker: And so like he's constantly dealing with the stress of being out of your comfort zone. Whereas Gary's dealing with different repertorial questions, but within the context of the comfort zone that he had set up for himself. And I think that like a lot of Gary's great work and I've got his collection over my shoulder. I mean, it's one of my, my favorite books. A lot of those, those stories that I love are not stories that check all those boxes. It was when his standard was different and, you know, he would do stories without access or whatever it might be. And so I think that like,
Speaker: you know, it's it's the fear of plateauing. It's the fear of kind of developing into a comfort zone where your writing voice is kind of settled and you bring it to each story. i For a long time, I struggled with developing a writing voice. Like Wright and Justin, you know they had their voices in college. I mean, you know they you know I'm not saying they were born with their voices, but they they just like they knew how to do it. And it's something I struggled with for a long time.
Speaker: And I always thought, like you know you get your writing voice and you hang on to it. yeah When in fact, I think that like it changes, has to adapt to each story. It has to be something that is malleable.
Speaker: you know I think that if you're kind of bringing the same perspective to each story, and I'm not saying Justin Wright do, but I'm saying if you you know i think that like if you settle on your perspective and you bring it to each story without room for adaption, room for being wrong, you know ah saw an assumption being wrong in a story. so Tom Junot once said, he was like, you know one of the best things you can do is have the premise for your story be wrong.
Speaker: because you learn so much more that way and it helps you as a storyteller. And so, you know, again, I think that like the more you can get out of your comfort zone and be challenged, it gives you not only confidence as a reporter and as a writer, but you also, you keep getting better and you keep improving.
Speaker: And it'll surprise your audience because you're getting these different stories each time out and it's unpredictable to them too, what's what's going to come. Yeah. Where do you see yourself like pushing yourself to next?
Speaker: um
Speaker: That's a great question. You know, I've written so much about football. I easily could have put every story in there, you know, ah football, they they all aren't. And I'm proud of some of the stories that I do that, that, and I've done that, that aren't about football. But I think that like, I think that I want to try to take some of the intensity that I've attacked football with and bring it to other sports. and you know, I think that other sports are kind of fertile for me to go in there a little bit fresher than I have been.
Speaker: Because, you know, in football, I kind of have this base of knowledge that I'm drawing upon each time. And so sometimes people will say things to me or I'll witness things that don't register like they should because I've kind of seen it or I've been there or I've been, you know, I think I know what's gonna happen. And I think that like, just again,
Speaker: Putting my feet on uncertain ground, I think is what I want to do, whether it's college sports and the, you know, the atmosphere there and the structure there or the lack of the structure, whatever it is.
Speaker: You know, I just think there's some good opportunities to, to go beyond football. You know, I've majored in football and i kind of minor in these other sports and, you know maybe do a major in the future. I don't, I don't know.
Speaker: Yeah. And Wright's introduction ah to Beyond That Hill, too. He he writes, yeah there are 28 stories by a modern master. And because he's a modern master, ah they are all chapters in one story, his story, our story. So what do you make of that?
Speaker: Well, I mean, what a compliment. um I think that, again, it's like these things reflect, you know, your interests and your curiosities. And it's why...
Speaker: it's what changes, you know, at some point you become a writer where people might see your name attached to something and maybe they don't know what they're going to get exactly, but they, they're interested in it because you kind of have a product, you know, for lack of a better word, you know what I mean? it Like Rick telling you, of my buddies. Yeah.
Speaker: Yeah. He, he once said that he goes, you know, eventually you kind of, you know, you, you write and you write and youre write, but eventually you kind of develop a product and people want, to see whatever it is through your eyes. And so I think that like, that's what Wright's getting at with that. And um it's not something I set out to do, you know, like, again, you know, that's that's kind of where those stories live.
Speaker: And, you know, he's had a front row seat to it. So it was really cool that he made that observation. Yeah, well, for sure. And like in speaking of a you know that kind of that idea of branding, it's like when you when you see a a Pam Koloff or a Tom Junot byline or a Seth or a Wright or a Justin, and you're like, okay, it's just like, I don't care what this is about, but I just know I'm in for a good ride. And I think you know through the 26 years that you've been at ESPN and counting,
Speaker: that's what we have come to expect now. I know when I see your byline come out like, Oh, oh cool. I'm going to carve out my morning for this one. And that's a testament to the body of work you've done in the, the rigor through which you've done this for a quarter century.
Speaker: Thanks, man. I appreciate that. You know, again, and I know the feeling, you know, you don't, you don't ever feel like, you know, you're at the level of those people or you don't think about it as, Hey, you know, this story is coming out and,
Speaker: people are gonna wanna read it because I wrote it. Because you can't ever, story wouldn't get published. You know what mean? If that's the mentality you went into it, it's like, what can I learn and how best can I tell it? But I know the feeling because I read those people whether was growing you know growing up Jim Murray. you know i loved you know When I was in college, i just loved reading Jim Murray's stuff. Frank DeFord, Gary Smith, Tom, Rick Riley, Rick Tallender, all those guys. Michael Wilbon, after I was at the Washington Post, I really gained ah an appreciation for his writing and his eyes. and
Speaker: I know, i know the feeling that you're talking about and, you know, Pam's book just came out and I'm reading it and, you know, nobody else could have done that book, but her. yeah And that part of it is really cool because it's never been easier to get your thoughts out into the world, but there's some people who are really special in what they do and, um, their thoughts are different and you know, that it's cool to, you know, to,
Speaker: watch them do what they've done and to try to achieve it myself. Oh, it's amazing. Well, Seth, my gosh, it's it's so great that we've been able to have like several of these conversations over the years. And I'm so glad we get to celebrate beyond that hill and the body sampling of the body of work you've built up over a quarter century, which must sound kind of weird. So like quarters. Oh my God. that's weird It's like a long time. hu Well, it's like, I'm not precocious anymore, you know? And like, it was fun to be precocious. Yeah. And now you're in the old guard. You've like crossed a membrane. um um I've passed it like twice because then it's like, you know, you're kind of, you know, you're precocious in your 20s.
Speaker: You're rolling in your in your 30s and in your 40s and hopefully into the 50s. You know, you're this finely tuned machine that, you know, can, you know, go out in the world and, you know, come back with a story that people want to read, you know, that's the goal, but it is different. It is different. Then there are benefits and um issues with being precocious, but it's a fun time.
Speaker: Absolutely, man. Well, as always, just thank you so much for the work and thanks for carving time to talk shop and yeah, and just best of luck with this book and can't wait till we get to do this again sometime. Thanks, man. i appreciate
Speaker: Yes. Awesome. Pretty great, right? I mean, we always knew we knew it was going to be great, but it always it always seems to exceed my expectations when talking to Seth. Now, my feeling is the best books on writing are anthologies.
Speaker: Because they are high watermarks of masters. And by rereading them, by excavating them, by stripping them down to their studs, that is a better way to learn craft than any craft book, in my opinion.
Speaker: Interrogate it, mimic it, mark it up. And thanks to Seth. As always, for being such a kind and generous friend of the show, I will mark the shit out of Beyond That Hill. Already have although a little bit.
Speaker: it's good More. More's coming. And I sure hope you sign up for Pitch Club at WelcomeToPitchClub.com. Oh, no, no. Ah, see, i am thinking of getting a website to to host the archive of Pitch Club.
Speaker: But to in its current manifestation, WelcomeToPitchClub.substack.com. Maybe I can lobby Seth to hop on for a source pitch. um But I've bugged him a lot lately. I mean, it's all in favor of celebrating his work and all, but I don't want things to get weird. Follow the show on Instagram at Creative Nonfiction Podcast and visit brendanomero.com for show notes and blog posts and tasteful news and to sign up for both of those newsletters and to just, you know, have a good time.
Speaker: All right, so I'm recording this on a Tuesday morning because I'm zipping down to Austin, Texas. Austin, Massachusetts. To attend the Dan Jenkins Medal for Excellence in Sports Writing Awards. Have you seen Road Trip in a while?
Speaker: When was the last time you saw a Road Trip? If you know, you know. Some of you may know that the frontrunner was one of 12 finalists, among them being the authors Seth Wickersham, you may have heard of him, Sally Jenkins, Jane Levy, Hanifa Durrakeb, and S.L. Price.
Speaker: By the time you hear this, i will be on my way back from Texas, the first time I have ever entered the borders of the Lone Star State. S.L. Price has already been announced as the winner of the best sports book for his book on lacrosse, An American Game.
Speaker: I hope some of the finalists will be down there so I can meet them in schmooze. I'm not so sure any of them will go, but I forked up a pretty penny to go, so I'm going to go there and celebrate Austin.
Speaker: Austin, Massachusetts. But this is a parting shot about the path, or my path, or why I still struggle to accept it for what it is. You see, Seth's collection stirred up in me these pangs of kind of like career regret or even career envy in me because that's the kind of work I've long wanted to do.
Speaker: And maybe at this point it's not possible, or like that ship has sailed. I don't know. And for myriad reasons, many in my control, but some not. My path is not provided for that.
Speaker: And I have to reckon with the fact that I'll be lucky to write a single feature in my lifetime of that caliber, let alone having an anthology of them. and I want to be of that crew. I've always wanted to be of that fraternity or just that crew. You know, to be in and among that crew.
Speaker: Some might argue in a weird, se circuitous way, I kind of sort of am. I mean, the Dan Jenkins Medal for Excellence in Sports Writing. yeah If you look at the names of the other finalists, you'd be like, your book is among them? Then you're in the crew.
Speaker: You're in the gang, man. What am I trying to say? I guess when I was really ginning up the writing mill some 20 years ago, the work in Seth's book was the kind I so desperately wanted to do.
Speaker: And it was my failure of skill and rigor that it didn't happen when it hasn't happened yet. And if it it hasn't happened yet, is it ever going to happen? But a media climate at that time when I got spit out of college and even spit out of the MFA program, it just it was contracting and continues to contract. And even though there are many opportunities available now that weren't available in 2011, there's always things changing underfoot.
Speaker: Who knew what Substack would be? you know And that's been a boondoggle for some people. I got an MFA in 2008, and I thought that would be this accelerant. you know It was many things, but it wasn't that. And the best advice I got from two years in that program was from the Pulitzer Prize winner and one of my mentors there, Tom French, who I don't think likes me. He doesn't return he hasn't returned an email of mine in years.
Speaker: It's neither here nor there, but I was like, oh. Maybe this guy just doesn't like me anymore. And he was like, Brendan, sometimes we write books and they don't get published. And his vice his advice was basically, move the fuck on. Which is a hard pill to swallow, but it's the hard truth that a lot of us have to embrace. And then, yeah.
Speaker: you don't publish that book that you worked for years on, it's okay. It's actually kind of normal. Move on to the next one. And you're one book better. Book writing takes book practice. Not a lot of people want to talk about that either. You think because you spent all that time on that book, you're like, well, this deserves to be published. And it's like, eh, maybe not. Maybe it was just practice.
Speaker: it was nothing It wasn't wasted. Speaking of waste, I wasted my 30s trying to freelance long stories and failing and then getting... scooped up by menial jobs that robbed me of my time to get better at pitching stories, writing stories, etc. You might say that maybe I was hiding in the the short-term fix of an hourly wage job to pay the bills and so forth.
Speaker: I don't know. This was the cycle for me that started in about 2009 to about 2019. It wasn't the path I signed up for out of college. I felt like such a loser while people around me seemed to be like crushing it.
Speaker: and that voice crushing it. There was a cohort of youngish freelancer types you know writing for SB Nation Long Form, and I couldn't land the story there, and they all just seemed to be getting anthologized in Best American Sports Writing. It's like, fuck, that's, goddammit, that's where I want to be.
Speaker: i just couldn't bridge that gap between what I wanted and my skill and then the opportunity, and then I was off to another retail job or something. Yeah.
Speaker: Yeah, I pull the ripcord too soon often. That's ah probably a parting shot for another day. and And others were writing for Grantland or Outside Magazine and some other really cool places. And then maybe as a result of writing for those cool places, they were getting like scooped up by the New Yorker or something.
Speaker: I think like Gia Tolentino. Like she was one of those who, not that I'm in her class, I'm saying that, but as she was writing for like Jezebel and other places, like bloggier places. And then, yeah, the New Yorker's like, you're ours now.
Speaker: ah Meanwhile, I was writing many like shitty slideshows in the occasional feature for Bleacher Report, and I thought that might have been something that I could springboard to something greater, but that never parlayed itself into anything.
Speaker: It just made me frustrated that I would be sitting on my couch often for... six hours watching a NASCAR race to get paid 50 bucks and then encouraged to like engage in comments and all this stuff. And like, this just isn't worth it. I did that for many years, good, good three or four, even five years.
Speaker: doesn't matter. Around this time, I started the podcast, you may have heard of, but ah got, quote unquote, overtaken by long form because they had the guts and the strategy to do it weekly from the get go. Well, I did it when I felt like it.
Speaker: you know So while we started around the same time, they didn't really get that much of a jump on me in terms of when they started. Only a few months, really. They ended up amassing 200 or so episodes to about 30, to my 30 by the time I started ginning up the mill. I keep using that term, but yes, when I started to do it consistently. And then they as a result, they won and earned the attention of many, many thousands of people.
Speaker: And they also had three co-hosts who are also, know, they were all based in New York and had an infrastructure around them that I lacked that allowed them to do that weekly from the from the jump. You know, this podcast here has become something nice over the years, but it is it still pales in comparison to what they had amassed before sunsetting. And even when they sunsetted, I started to think, oh, oh maybe I'll get, I'm going to get like that audience now.
Speaker: like, that'd be cool. Hopefully they just poured over. But I think i think like anything, i probably people in that audience were like relieved when they that they didn't have like that pressure of listening to the weekly show anymore. And just so like, oh, cool. Now I don't have to listen to this thing anymore. and They can move on to something else. It's not like, oh, cool. Now we're we're going to go listen to the to that guy over there who is so something of an insufferable voice in the in the creative space.
Speaker: ah Yes, as you well know, I'm something of an acquired taste and maybe a bit of a crybaby and definitely insufferable at times. But this show has a toehold, even if it's a tiny one, small and mighty. And I've been lucky to have I had a university press book, my very first one in 2011 and of course 2025.
Speaker: four in twenty twenty five You know, a big five book deal with the front runner and who knows what and when the next one will be Still haven't heard back from my representative. It's going on three months now, which at this point is kind of rude. But whatever.
Speaker: Whatever. I still struggle with this path I'm on, if you can't tell. I'm still in many ways waiting for my career to start. I know it sounds kind of crazy, but I still feel like there's been this failure to launch.
Speaker: Even with a a couple books and some speaking here and there and the occasional freelancing piece here and there. you know In my head, I'm still that scrappy 27-year-old waiting for life to start.
Speaker: And well, buddy... you better snap out of that because it's been 20 years. You don't have much time left. I think I just talked with Matt Wolf, like i like truly, I might have 40 years left on the planet.
Speaker: And you figure maybe the last 10 years of that, I'm not going to be doing much by way of what I'm doing now. so that's like maybe 30 years to keep, you know, maybe do a couple books or whatever podcast manifestations are going to be happening the next 30 years.
Speaker: It's like, you know, you don't have much time. And I'm terrified of dying. I really am. Anyway, I have a bad case of the compare virus. I look at the paths of others and I think I want that. The grass is always greener. You know, that kind of thing.
Speaker: yeah I expect there are some who look at my path or how they interpret it from the outside and they're like, oh, I want that. That seems pretty cool what Brendan's done. So I'm at least trying to be a little self-aware here.
Speaker: I feel I use the podcast as a way to hide sometimes and to not do the work that lights me up. and i lose myself in the work of others so I don't have to do any myself. And that bumps me out on some level.
Speaker: you know See the fear of death. And I know this is my path, and it's unique to me. It certainly is. No one else could replicate it. I think I've said before, I've written somewhere, like if you try to like Xerox or photocopy my career path, you're going to get a fucking paper jam to end all paper jams. you know I could have never envisioned that this podcast would be a thing, such as it is, that people would like to hang out with me every week, sometimes, and learn a bit from the people who join me.
Speaker: yeah It's very unique to me and an extension of my very often, I've used this word before already, insufferable personality. It's how I express myself and share of myself. It's how I found my true voice as a writer.
Speaker: Seriously, when i when I get to writing, rare as it seems these days, I have a confidence to be singularly me, I just have an embridled sense of of once I get to writing, it's, it just kind of, I'm not going to say it flows out of me, but I do have a certain comfort in who I am when I start to writing.
Speaker: I talked to, you know, so many people and they all have these weird windy paths through this world and, I don't know why I've struggled embracing mine while admiring others.
Speaker: yeah Again, I come back to that grass is always greener. Sometimes it's hard to just embrace your own past. It seems like everybody else's has been a bit more greased up, a road without the potholes.
Speaker: But yeah, that's bullshit. But when you don't have the full story, you paint it in yourself. Okay. We're all just trying to make a go of it. and And maybe the ones who are the most content are the ones who do the least comparing.
Speaker: I try not to, but it's only natural to compare yourself to others who are getting new book deals while yours is rejected or that guest you've been after for months on a podcast tells you no, they're not doing the podcast scene only to then appear on someone else's show or do several other shows while they said no to you, while they told you they weren't doing it.
Speaker: Or that podcast appear to be even more popular than yours, even though you've been doing it for three or four times as long. And I'm like, why do I put myself through all this shit? Maybe I'm like, i don't have the head to be a creative person because of this. I'm too insecure. Maybe maybe maybe ah maybe i am one of those people like who should just work at the grocery store.
Speaker: you know, this was supposed to be a parting shot about embracing my path and feeling good about it. And deep down, truly, I do. I do. I mean, I'm grateful that I get to do this, that I get to spend this time with you, that you even make it this far to listen.
Speaker: There's a kinship here, and I think ah i think we have fun with it. I mean, I'm 46 now. I better embrace it because it's all I have. And the way things are going in this final quarter of 2026, I'll be applying to Trader Joe's in 2027. So stay wild, CNFers. And if you can't do, interview. See
