I recently came across this scenario by Chuck Klosterman:
Klosterman: “Let me frame it like this: You’re at a book signing. A kid comes up to you. You can tell the kid is smart. Just from his demeanor and the way he talks, the way he looks, the other books he has with him. Which compliment makes you feel better? ‘You’re my favorite writer’ or if he says, ‘I’m a writer. I want to be like you.’
The scenario above is from one of those podcast appearances. Bill picked #2:
Simmons: “I just know that when the roles were reversed, the writers that meant something to me were also the writers that made me want to write.”
To succeed as a writer, it’s helpful to decide what success looks like. Begin with the end in mind and all of that. I’ve had fun reading Simmons’s writing through the years, so I did a small dive through some of Bill’s career to pick up some pointers on how to progress as a writer.
These three things gave me the most insight into his writing career, going backwards:
- B.S. Report: ESPN 20th Anniversary (April 3, 2015 aka Fast 7 Day) — He says he’ll talk about his career for 15 minutes. If you thought 15 minutes would be enough for him, you probably thought a 680-word column in ESPN The Magazine would be enough for him. He goes on for 40 minutes and it’s a great look back at his own career. It’s a month before the end of his career at ESPN, bringing an abrupt end to Grantland.
- B.S. Report: Chuck Klosterman (March 3, 2011) — Sometime in the podcast, Bill switches subjects. “So you wanna talk about Grantland…?” Then he says Klosterman’s the first writer he asked to write for Grantland and they go over what the site will be and what Bill’s vision is for the site.
- The Ramblings in The Crusader (1989-1991) — The beginning. The clippings scattered throughout this post are from those columns.
Conclusion: Osmosis doesn’t work. You have to write.
1.) Write about something you love (grow up attending Celtics games)
Bill loves sports and he always has. In a recent live recording from NYC’s Advertising Week, Malcolm Gladwell asks Bill what 14-year old Bill Simmons was like. Here’s Bill:
14-year old Bill Simmons. What year are we in, 1983? I woulda been in disbelief that I got to write anything about sports and people read it and I got paid for it. You could’ve told me that I made 8 dollars an hour and I would’ve been like, “Oh my god, this is amazing.”
Malcolm: I want to know about. What. 14-year-old Bill Simmons is doing what. Is he… how insane a sports fan is he?
Bill: Oh I have this picture of my room. It’s pathetic. It’s just covered in sports stuff. There’s not a girl to be seen. I was just obsessed with sports. I was an only child. It was just sports. Boston sports. Everything. I remember with the ’84 Olympics, I think I might’ve seen every minute of the ’84 Olympics because it was in LA. I might’ve just watched all of it.
Gladwell: It wasn’t just. It was all sports?
Bill: I loved sports, yeah.
If you love sports, you have moments magnified to heartbreaks because it happened when you were a kid. Usually it’s your first time watching your team lose in the playoffs when you’re able to understand what playoffs are (mine: March 31, 1996). Sometimes that heartbreak comes through incidents off the court.
One of Bill’s first articles on Page 2 was “Still haunted by Len Bias”. He says he was really proud of it and it was written in the 5-week break he took before joining. Bill recently had Nathan Fielder on as a guest. Cocaine came up and Bill says he hasn’t done it, ever, and has somehow managed to never be in a room with it.
Bill: When I was 16, the Celtics drafted this guy Len Bias who was like the number two pick in the draft that year. And he’s this guy was going to be like our best player and he overdosed on cocaine two days later and that like legitimately scared me from drugs after that.
Before building an internet following, one of his college Ramblings columns (1989) was also dedicated to Len Bias.
Bill loved the Boston Celtics. He loved basketball. He loved sports. He still does.
2.) Write a lot (get your reps in)
Simmons seems to have an encyclopedic knowledge of all sports writers from the 70s and 80s. Bill read a lot of good writing growing up. He’s hired talented writers at The Ringer and Grantland. He often has other writers on his podcast. I’ve mentioned Klosterman and Gladwell. He recently had Ta-Nehisi Coates on.
It’s hard to write as much as Simmons did for as long as he did without loving it. He told Gladwell he wrote short stories as a kid. He had The Ramblings in college.
It seems like the biggest grind was becoming the Boston Sports Guy. On that ESPN 20th anniversary podcast, he goes over his daily routine. Day in, day out, it was links, lunch, and columns.
- Links: He would spend the morning opening link after link and writing about the best ones to share. Then he’d put them up on his site and then head to lunch
- Lunch: Pizza. (Years later, he defended gluten-free crust on a Half-Baked Ideas episode. Pizza The Interruption.)
- Columns: After lunch, he’d work on his columns to post 2-3 each week.
Day in, day out, week in, week out. Month after month. Writing columns and sharing links he had to open on a 28k modem. (And no tabbed browser!) All while tuning in and out of ER and 90210 reruns he kept going in the background.
Down the line, Simmons moved to LA to write for season 1 of Jimmy Kimmel Live. He was on a roof in New York and the team was filming a segment with Mike Tyson and his birds.
On the roof, Simmons says he was standing there thinking about how this experience would work in his writing instead of focusing on how this was going to work for TV show. That’s when he knew that he was meant to write.
(He did write about it. Page 2: Meeting Iron Mike.)
3.) Find your voice in other people’s voices (Figure out your go-to moves)
In his ESPN mailbags, you could always count on Bill asking himself a question. It was always a fun gag. One of his Ramblings (’91 Nov) is a Q&A entirely of questions he wrote to himself.
In the ESPN 20th Anniversary podcast, he says he started figuring out what his voice was around 1999. (Captured in a piece about Vegas where he ran into The Undertaker in the bathroom.) That’s 7 years after his last Ramblings in The Crusader. It wasn’t dabbling here and there, either. It takes time to find your voice.
On the Chuck Klosterman episode, Simmons talks about finding your voice as a writer:
Bill: “I feel the same way about that as I would with anybody. Writers when they’re trying to figure out what their style is, they end up mimicking people they’re reading. And you don’t really have your full style until you’ve taken all of the different writers you like and your style becomes pieces of those people. Right? That’s when you become an actual writer. I would say, I don’t know who your four or five influences were, but those influences conspired to turn you into the style that you have.”
When he got the AOL deal he wanted to do things his way. “If I’m gonna go down in flames, I’m gonna go down in flames like me.”
(The deal being $50 per week for 3 months.)
These were the go-to moves he knew he could use:
- Ramblings: Mike Lupica used to do these one liners and he wanted to do something similar. The Ramblings were his bread and butter at Holy Cross.
- The mailbag: He grew up loving David Letterman and wanted to involve readers like he involved viewers. These were always my favorite things to read.
- NFL picks: He says he loved Pete Axthelm’s gambling column in _Inside Sports_ and wanted to do something similar.
- NBA and Boston teams: More bread and butter. Bill loves basketball. Simmons mentions something he wrote being on ESPN ahead of something by David Halberstam (Breaks of the Game) when describing how he knew he had something going.
- A ton of pop culture: Ok so this full list is a lot bread and a lot of butter.
When he moved to Page 2, he kept the moves with some changes, like a modified swing. The biggest switch he made was switching local references to pop culture. It made sense, going from a Boston audience to a national audience.
Those go-to moves live on:
- NFL picks: The last survivors in written form in his weekly Ringer column
- The Ramblings: Now found one line at a time on his Twitter feed. (Listening to the old Klosterman episodes reminded me that Simmons held out on Twitter for what seemed like a really long time for a writer so tuned into pop culture.)
- Mailbag: Written responses once in a while, but usually he’ll answer questions on his podcast
- Basketball and pop culture: Flourishing in podcast form
The voice he developed over decades is magnified in the collective voice of The Ringer. (RIP Grantland!)
4.) Try the other things, too
There’s a post on the Holy Cross site covering Bill’s success at the time (2001):
And he’s been at it since, doing a job that most of us would love to do every day. When asked what he would do with the rest of his life if he could do anything at all, Simmons replies, “Pretty much what I’m doing right now – writing about sports… Although eventually I’d like to write a couple books and maybe try some screenplays.”
I learned about The Sports Guy through my brother (a much bigger sports fan than me). Now I can’t remember if he sent me the link or I was just being nosy. I remember enjoying how different the writing was from other sports articles. They were 1.) intended to be funny and 2.) was actually funny.
Simmons says he got on ESPN’s radar with his running diary for ESPYs. It was inspired by Norman Chad’s running diaries of different games in The National. Bill liked the timestamps format so he tried to blow it out. The timestamps gave his ramblings a narrative.
(In high school and college, I tried writing live blogs for things like the mysterious Blizzard announcement that ended up being Starcraft 2. I did it earlier this year for a very long walk that I took to try to get into ketosis. I can only match the “intended to be funny” part without the follow through of actually being funny.)
Here’s another example of something you’d never find in a newspaper’s sports section: First Annual Atrocious GM Summit (2006). It’s written as a transcript. I’m sure his interest writing screenplays helped. And his experience writing for Jimmy Kimmel Live helped even more.
Fifteen years before that, he was, as always, getting his reps in.
5.) Make cool friends
Simmons has always included his friends in his writing.
- The House headline to the right killed me when I was going through the Crusader archives. 26 years later, I can listen to House talking sports with David Chang House of Carbs.
- The article about his Vegas trip was pretty much entirely about his buddies
- “Complex litigation this is John.” OHHH JOHNNY
- Before Jalen and Jacoby there was, of course, Jacoby and Wildes (Half-baked Ideas are my favorite podcasts, period.)
- There’s Klosterman and Gladwell and the writers he’s made friends with
- He worked with Cousin Sal on Kimmel’s show and Cousin Sal is a staple guest on the podcast during the NFL season. On the right night, you can of course catch him on Instagram with House, eating their way through an entire Brooklyn food hall.
- And of course: his dad, who seems like the nicest person ever
Dave Dameshek was a recurring guest in the early days of the B.S. Report. Eventually I started listening to Dave’s podcast (which I think was just his radio show). He had an audio drop that me and my brother say to this day: “When I’m wrong I say I’m wrong”.
For decades, it seemed like it was just a competition between me and my brother to be able to say “I told you so” the most to the other person. It was the most powerful thing in the world. Then we started saying “When I’m wrong I say I’m wrong” and it de-fanged the entire thing. All of a sudden it seemed silly to take pride in pointing out that someone else is wrong. A small, important step toward becoming an adult.
6.) Find something else you love and repeat (Get your reps in, pt. II)
In Sex, Drugs, and Cocoa Puffs, Chuck Klosterman wrote a chapter about Saved By The Bell. Part of it is about how we remember high school and college as if we were with our friends 100% of the time.
Whenever I try to remember friends from high school, friends from college, or even just friends from five years ago, my memory always creates the illusion that we were together constantly, just like those kids on Saved by the Bell. However, this was almost never the case.
Every other night was some party. The highs (usually involving friends) stick. The boring gaps (class, studying, exams) fade away.
In 2008, I had a summer internship at IBM, writing page-turners like section 4.1 of Introduction to DB2 for z/OS. It was my first attempt at living on my own. I remember listening to the Bill Simmons podcast for hours on end during work and on my commute.
Of course, I’m misremembering. I wouldn’t listen to an episode more than twice at most. There wasn’t enough audio to fill a work day, much less a week. It was the first podcast I listened to. Now I listen to a bunch every day so when I think back almost a decade, I misremember it as if I always listened to a bunch of podcasts.
He talks about starting his podcast at ESPN in this Sports Business Daily article (2009):
“I thought it would give me some reps, and help me get rid of vocal tics if I ever wanted to do anything down the road with TV and radio,” he said. “It would keep my options open.”
It didn’t take long for ESPN to agree, and they quickly outfitted Simmons with “a weird machine, two headphones, [and] an ISDN line in my house.”
Today you actually can fill a day with podcasts from his podcast and others on his podcast network. A decade ago, Bill was getting his podcast reps in. He became a successful podcaster the same way he succeeded with writing.
Bill Simmons made a ton of stuff and put it on the internet.
Back to Klosterman’s hypothetical scenario with the kid saying:
- (A) You’re my favorite writer
- (B) I’m a writer, I want to be like you.
I’d be happy to write even 10% as entertaining as Bill or Chuck. I’ve put in 1% of the time that they have to writing, so I’ve got a long way to go even to get to that 10%.
Klosterman presented Bill with a similar scenario with an even better setup.
For some reason, you’re dying of a disease slowly. To the point where the person from the New York Times or the LA Times writing this is talking to you at your bedside. You’ve kind of established a weird rapport with them. You’re very good friends now. He’s basically telling you what he’s going to write when you’ve passed. Because let’s say you’ve got a great demeanor, you’re making jokes about your own death. And he says look, I’ve got two ledes. Which one do you feel better about?
- (A) You’re one of the greatest sports writers of all time
- (B) You’re the most influential sports writers of all time
Bill’s response? “I don’t think either would be said.” Further along:
“The writers that meant something to me were also the writers that made me want to write. So I guess like… it would be more fun to be in that conversation where you’re thinking, you know, once you’re older and you have people who got into writing and they said, ‘Here are the five or six writers that made me want to do this for a living and you were one of those writers’ I think that would mean the most.”
I’m sure Bill Simmons has made a lot of people want to write for a living.