All Careers Considered: Working in the Sports Industry and Becoming an Author with Julie DiCaro

This week we spoke with Julie DiCaro. Julie graduated in 1995 with a degree in Journalism. She currently works at Deadspin as a Senior Editor and recently released a book titled Sidelined: Sports, Culture, and Being a Woman in America.  In this episode, Julie shares why she chose to attend law school right after graduating from IU, how she transitioned into the sports industry, and what it was like to write and publish her own book.

This is the last episode of this season of the podcast. Thanks for listening and please check back for more podcast content in the fall!


MOLLY: Hey Hoosiers, and welcome back to another episode of All Careers Considered. This podcast is produced by the Walter Center for Career Achievement, which is the career services center that specifically serves students and alumni and the College of Arts and Sciences, IU Bloomington. We’re on a mission to help you achieve career success by supporting you and your pursuit of impactful experiences, designing your life, sharing your story and building meaningful connections.

My name is Molly. I’m the assistant director of strategic alumni engagement for the Walter Center, and I’m also the host of this podcast. You may have heard that you can do anything with the College of Arts and Sciences degree, and I’m here to show you that that really is the case by interviewing alumni to ask them how they got to where they are now. Next up is my interview with Julie DiCaro. Julie graduated from IU Bloomington in 1995, with a degree in Journalism. She currently works at Deadspin as a senior editor, and recently released a book titled Sidelined Sports Culture and Being a Woman in America. In this episode, we had a great conversation where Julie shared with me why she chose to attend law school right after graduating from IU, how she transitioned into the sports industry and what it was like to write and publish your own book. Enjoy!

Alrighty. Thank you for being here, Julie.

JULIE: Thanks for having me.

MOLLY: Yeah. So I’m really excited to talk to you today. I mean, I know you’ve had a really successful career as a sports journalist, as an editor, and you actually just recently published a book, which I’m super excited to talk to you about. So there’s so many things to cover, but I’d love to start with just hearing a little bit about the work you’re doing right now. I saw that you are working at a company called Deadspin and also doing some freelance work. So I’d love for you to just tell me more about that.

JULIE: I am. Yeah. I mean, I haven’t been freelancing since I got to Deadspin a year ago. I’ve been working on the book and I’ve been doing this. So freelancing was sort of what I did. The radio station, where I was working from like what, 2015 to 2020 you know, didn’t do a great job promoting their work. And, and a lot of the stuff that I write about, they weren’t necessarily interested in. So I started reaching out to outlets like the Washington Post, the New York Times you know, to, to try to play some of that stuff. And so that is, that is where I was freelancing. I, you know, I still guess I will, if I’m just writing about feminist topics that, that aren’t related to sports, but for right now I’m doing mostly sports writing. So it’s all going to Deadspin.

MOLLY: Super cool. Awesome. And then when you were, you know, kind of backtracking thinking about when you went to NYU, where you kind of dreaming of being a sports journalist, or what were you kind of thinking that your career trajectory was going to look like?

JULIE: So what I really wanted to do was play by play for the Chicago Cubs. But there was nobody doing… there were no women doing that, I mean. And I would see women in here or there in sports. He saw Lesley Visser always on interviewing college basketball players and NBA players. And you know, Melissa Isaacson was covering the bulls for Chicago Tribune, but the women that I saw on TV doing sports or heard on the radio, I didn’t hear any on the radio were pretty few and far between.

So when I graduated from IU I, I didn’t really see the path to get to what I wanted to do from where I was. And of course back at that time, IU didn’t have the sports broadcasting programs and, you know, the even like the, the radio station and the TV station and everything like they do now I think that was, I don’t think we had a TV station at all, and I think we were mostly, radio was mostly focused on music. So although that stuff sort of came after I was there. So I kind of had to find my own path, which is why I wound up going to law school and, you know, practicing law for 12 years or something along those lines. But when blogging became a thing and when sports blogs became a thing, that was sort of how I saw my opening. So I started a sports blog. Started writing, you know, about the Chicago Cubs and developed a following. And eventually that blog got picked up by the Chicago Tribune, which is how I sort of made my way into the industry.

MOLLY: Wow. That’s really interesting. I’m interested in a few things you said. The first one, being that when you were at IU they didn’t have a lot of like student organizations that there are now like the radio station and TV. So what types of things were you involved with in life while you were a student? I mean, was there any type of, did you do any internships or what was your life like as a student, as you were kind of preparing for what your career would be.

JULIE: I well, I was in a sorority and I was in, I wrote for the IDS and played a lot of intermural sports. I mean, so it just kind of stuff like that. You know, I, I, there may have been a TV station as far as I know. I know there’s a radio station, but my point was the sports broadcasting component of it. Wasn’t sure like it is today. And I think Bobby Knight, if I recall correctly, didn’t even want students covering the basketball team. So I was in student athletic board. I mean, you know, so sort of around sports, but I didn’t have the opportunity to cover sports the way that I do now.

MOLLY: Yeah, absolutely. That makes sense. So tell me a little bit about your decision to go to law school. What was kind of the thought process there?

JULIE: I think the thought process everyone has when they go to law school, which is, I don’t know what else to do. So, I mean, I really, I didn’t know what I wanted to do. I was interested in law and this is hilarious because I loved Law and Order. I loved Law and Order, and I was like, I can do that. That’d be kind of cool. So I, I went to law school and I became a public defender. And that was a job that I loved. If I could have stayed a public defender forever I would have, but it’s tough to do, you know, eight, 8:00 PM jury trials and wait for a verdict to come back and everything when you have small children. So yeah, someday maybe I’ll go back to being a public defender, but yeah, it was I just didn’t know what else I wanted to do. And I was smart, and I got good grades on the LSAT. I got a good score on the LSATand DePaul offered me a scholarship. So I was like, all right, I guess I’ll do this. I really didn’t put a lot of thought into it in hindsight, which is ridiculous. When you think of how much law school costs, I mean, it’s like having another mortgage on your house in student loan money. So I would encourage anyone who’s thinking about law school unless you really, really want to be a lawyer and you absolutely can’t do what you want to do without a lot degree, think about it.

MOLLY: And then, so did you, how many years, just to kind of get a sense of your, the timeline here, how many years between, when you graduated from IU did you go to law school? Was it right after graduate from IU?

JULIE: Right away.

MOLLY: Okay.

JULIE: Yeah, I bawled the entire way. My dad picked me up in Bloomington and I cried the entire way to Chicago because I’d been having the best time that summer with like zero responsibility. And so  you know, that was, I was at the bars every night and I was just having a great old time. And then my dad came, picked me up and was like, all right, time for you to move to Chicago. Cause I kept putting it off and putting it off and putting it off because I didn’t want to leave Bloomington. So my parents basically dragged me out of town kicking and screaming.

MOLLY: Yeah. I mean that a lot of, a lot of students are probably in that boat. Okay. This is such an interesting story. So you were at you’re at Bloomington and you were always dreaming of being a sports writer, but didn’t really see a path. And so then you kind of decided to go to law school and be a public defender. And then at what point did you kind of decide, like what made you decide that you didn’t want to do to be a public defender anymore? Was there like a specific thing that you were like, yeah, I don’t think this was the right decision.

JULIE: No, I mean, I think I’ve, I’ve loved being a public defender. And I do think that there is a fair amount of burnout that happens with public defenders and I am in awe of people that do it, their entire careers, or even do it for like, you know, 20 years because you literally are seeing people just get beaten down by the system and recycled through the system and you can’t do. And I live in a really conservative county, so it was really difficult to watch what was happening with my clients over and over and over again, and you see that, you know, your clients are being treated differently than white people are being treated and, you know or, you know, being treated differently than white rich people are being treated. And the whole thing is really sort of depressing. But the decision for me to leave was just because I could not do the schedule and have two small babies at home because they’re like 18 months apart. So about five years after I had been a public defender, I decided, all right, I’m going to stay home. I’m going to work from home, which is hilarious given how old my kids were. And I, you know, I did some various stuff for legal websites, which are just starting to get going. So I was like summarizing cases and everything, and that did not last very long. It was only a couple of years after that, that I went back to practicing law and my kids were old enough to go to daycare and stuff like that. But so it was kinda, I took a really circuitous path.

MOLLY: Yeah. Yeah. That’s really interesting. So when you kind of decided to, you know, get into kind of the sports, journalism and writing, how did you kind of make that step? Were there any you know, were you doing any networking? Were there any people you met in the industry that kind of helped you get your foot in the door? I just kind of think of that specific industry as being pretty competitive. Maybe that’s just kind of my interpretation of it, but what was that like, kind of getting your foot into the door, into that industry and getting more well-known and kind of taking those first steps when you were kind of earlier in your career?

JULIE: So it was you know, getting into that industry is very competitive, which is why I couldn’t figure out how to do it after I graduated at IU. It was just, I, you know, it was like, I didn’t know anybody. And I, you know, I had kids that I went to the media school with—back then it was the Ernie Pyle school of Journalism— who were like, oh yeah, my dad’s getting me a job at Sports Illustrated or, yeah like my dad knows this person and he’s going to be in at ESPN. And it was like, if you didn’t and I didn’t know anybody. So I didn’t know how to do that, how to network. I had no contacts. I had no idea where to start. And that’s why blogging was such sort of a blessing. I mean, when I mean, at one point would SB Nation was just getting started there were five sports blogs and the Cubs were one of them. And so I started hanging around that blog and I developed a following. And around the same time Twitter was getting going, and Facebook was getting going. There was a community of baseball fans out there. And that was sort of how I built my audience.

And then I remember it was like a huge, big deal that I had like 10,000 followers on Twitter at one point. And that was why, that’s how I got my foot in the door at the Chicago Tribune. So it was never like networking with people in the industry. It was always just working on social media to build an audience and then taking that audience to people and saying, look how many people read my stuff. That was really sort of how and that is still a valid way to get your foot in the door today. If you don’t know anybody work on your audience.

MOLLY: Yeah, absolutely. And when you were kind of you know, working on your audience and kind of putting out pieces in the blog and, you know, tweeting and everything, do you remember that being a very like busy time? I mean, just thinking of, kind of work-life balance, was it something that, you know, you were working every single day from 7:00 to 5:00 PM?

JULIE: Well, here’s the thing. I was still practicing law. So this was a hobby. And I was doing this every spare moment. So, and you know, it’s the whole, I mean, that was really what I wanted to do. So it didn’t feel like work to get up super early, to write a blog post about what happened the night before or something like that. Or I worked on that site every day, every spare minute. I mean, my husband was sick of it and he was like close the damn computer. One of my kids drew a picture of me at school for mother’s day project. And I like had my laptop open and started being in the picture, which is awful.. And so I was trying, and frankly, my legal career was probably suffering because I was spending so much time on this. I wasn’t spending time on my actual job. I was spending time on it, but I wasn’t doing all the extra things. I wasn’t networking. And I wasn’t going to like Bar Association, you know, after happy hours and stuff like that. I was just working on this. And so when I, eventually, you know, the Tribune sorta came to me and said, would you come in-house and sort of teach brands and teach other bloggers how to do what you did. And that was when I made the jump into media.

MOLLY: Hmm. Yeah. Very cool. And to switch gears a little bit, I mean, obviously I’d be remiss to mention your book that you published. So congratulations on that. It’s called Sidelined: Sports Culture and Being a Woman in America, which sounds super interesting. It’s on my list to read next. So tell me a little bit about the book and how you kind of got the inspiration to write the book.

JULIE: I think all writers figure they’ll write a book at some point, but I think it’s really easy to wake up one day and have been in industry for 20 years, and you still haven’t written a book. And that’s sort of where I was headed, except that I was always like, kind of screaming into the void about these issues on social, on Twitter and especially, and I, and one day I was sitting at my job in radio and I was yelling about something about women in sports media and the way we were being treated. And I got an email from a publisher who said, you know, I’ve been following you for a while. I see all your tweets. Like you should definitely organize this and put this into a book and stop giving this to people for free. And I, it was the first time I hadn’t really thought about it because I thought like a great American mystery novel or something like that.
But writing about this didn’t ever occur to me. I didn’t really think anybody would want to read it. So I much to their dismay. I got an agent who really believed in the book from day one. And when we finally shopped the book around the, the guy who emailed me, they didn’t want the book, but I found another publisher who did.

And so it was, I just like everything in my career. I feel like I just sort of fell ass backwards into it because I got some random email and I was like, yeah, I should do that. I mean, that’s exactly how my blog got picked up by the Tribute. And that’s exactly how I got into radio. Just an email from somebody being like, Hey, would you be interested in this? And me being like, sure, why not? I think that, you know, in an age and we’re bombarded with so many spam emails and stuff, I think it’s important to go through your spam text to go through your spam emails every once in a while, and just make sure that you’re not missing something really important in there.

MOLLY: Yeah, that is a really good point. And I think, especially for students that have, you know, a lot going on, it’s really important to just make sure that you’re keeping up with your emails and everything like that. Especially if you’re putting out really good content out into the universe that someone might be interested in. So that’s really cool. So tell me what that was like kind of in those early stages of writing the book. Was it as easy as you thought, as hard as you thought? Cause obviously you are a writer, but I’m wondering if writing a book is a little bit of a different process?

JULIE: Oh god, it was so hard Molly, I can’t even begin to tell you. So even putting the proposal together was just really difficult. I think we spent probably a year working on the proposal. So when you do a proposal for a non-fiction book, I think our proposal wound up being like 25 pages. I’m thinking like, Oh, it’s just a quick outline and you just, you know, say what you want to talk about in there. No, it is a much more involved process and thank god I had an agent that was willing to work with me on it. His name is Noah Ballard and he basically held my hand through the entire thing. And you know, I’m thinking, okay, writing a book is there’s, there’s 10 chapters. I just basically need to write like 10 long form articles on each thing. But then, you know, you start writing and you, after a while, you’re just like, okay, I didn’t really have anything to say, but this has anything else to say, but this is like, four pages. So I have a clearly I need to say more and did a lot of that. And that’s why they give you such a long time to write a book. So you can come back to it, you know, and you can add things and you can go, Oh, I forgot to mention this. Or, Hey, this just happened. I should put this in the book. But yeah, in the beginning, especially I, my editor was very much a cheerleader. Very much sort of a gentle task master keeping me on track because it was, it’s difficult. It’s, it’s, it’s much harder than you think it’s going to be. You think, you know, I’m a writer, I’ll just write a book, but it’s much more difficult than that.

MOLLY: Yeah, absolutely. So now that the book has published how are things going? What kind of feedback have you gotten from the book? I mean it’s so cool that you have, you know, a real published book out there.
It really is. The day it came, they sent you like a box of them. And I was just like, I couldn’t believe it. I was just kind of stunned for a while to actually hold it in your hands. It’s pretty cool. The reaction, yeah. Has been overwhelmingly positive. Trolls didn’t like a lot what I had to say, especially people who I mentioned by name in the book.

JULIE: So there was a backlash I knew there would be like the day it came out. I got a lot of backlash from people at like Barstool Sports and in places like that, where I had, you know, sort of called them out for the way they treat women. So, so that was not unexpected. And that stuff can be really tough, even if you’re used to it. Even if, you know, it’s coming, it’s never great to like open up social media and have 300 people that day telling you how much you suck. But you know, I, like I said, I was, I was hopefully mentally prepared for it and, you know, I have women all the time ask me, you know, or come to me when they’re in the middle of like being targeted on social media and it always passes. It feels like it’s not going to when you’re right in the middle of it, but it always passes.  And beyond that, it’s been kind of a whirlwind of TV, radio interviews, right. Radio interviews, podcasts, French interview, you know, but it’s also really cool to see your book and places like In Style and to be on like All Things Considered and, you know stuff that, you know, would never have happened to me if it hadn’t been for the book. So that was really cool having Ms. Magazine write about it. I mean, that was pretty great.

MOLLY: Yeah. And I feel like the message about your book with, you know, talking about misogyny and a lot of these industries is super important. And I feel like also with the Me Too movement, I mean, there’s obviously a lot of people who want this, these types of stories and information. So yeah, I can’t think of a more perfect topic. So for students that may be kind of, you know, hoping to have a career similar to yours, maybe they’re interested in writing or you know, starting a sports blog or maybe even writing their own book one day. What kind of advice would you give to those students?

JULIE: I think that especially for women, but not limited to women, is that you need to get really used to asking for what you want, promoting your own product, promoting yourself, and following up with people over and over and over, which is really difficult because nobody wants to be pushy. Nobody wants people to think you’re a pain. Nobody wants to be like, you know, harassing people during their dinner time or whatever. But I’ve noticed that, you know, the people that I know that, you know, at one point we were at like the same place in our career. But this person was sort of a shameless self promoter, and now he is like a big shot and has a ton of followers and has all kinds of, you know he’s like huge platform. And that really was a lesson to me in, you know, nobody else is going to promote you. You need to do your own promotion. So get used to not just sharing something you wrote on social media once share it four or five times. Like he, you know, And for people to share it. If you are covering, you know, high school sports, but you eventually want to cover the pros, make sure your boss knows that your ultimate goal is that you want to cover pro sports, get used to asking for what you want, which again, I think for women especially is uncomfortable especially in an industry where people are constantly telling you, you’re lucky just to have a job. So I think sort of, you know, getting used to really putting yourself out there and not being ashamed to put yourself out there is, is something to get used to.

MOLLY: Yeah. And I feel like yeah, it’s like the time is here for women to kind of step up and ask for what they want, but also support each other, so I think that’s great.

JULIE: Absolutely. Yeah. And I always tell women you know, there are so few spots for us in this industry that we tend to look at each other as competition. And we absolutely cannot do that. If there are, if there’s room for ten hundred thousand billion white guys in this industry, there are room for all the women. And at the end of the day, when you have a rough day, it’s going to be the other women in the industry that are going to pick you up and dust you off and push you back out there because they know what you’re going through. And so having female friends and female allies is hugely important.

MOLLY: Yeah absolutely. Well thank you so much, Julie. It’s been great kind of getting to chat with you today and hearing more about your career. And like I said, I’m excited to read your book, but if students have any questions or maybe they just want to connect with you or you know, stay in touch with what you’re up to, is there a place that they could find you maybe online or social media?

JULIE: For sure, I’m @JulieDicaro on every social media platform. And I’m also on the Walter Center Success Network. Yep. Yes. The success network. Yeah. So they can find me there as well. And they can always email me at JulieDiCaro@gmail

MOLLY: Okay, perfect. Well, thank you so much, Julie it’s been great talking to you.

JULIE: Thanks for having me. All right, bye.

MOLLY: Thanks so much for listening today to learn. More about the Walter Center and the services, resources, and events we offer. Please check out. Our website at To get social media updates on all things happening in the Walter Center, please find us on Twitter, Instagram, and Facebook. To connect with alumni like the one in this episode, I definitely recommend making a profile on the Walter Center Success Network. It only takes a few minutes to create an account and start connecting with alumni. If you liked what you heard today, be sure to subscribe on Spotify, Apple podcasts, or wherever you get your podcast to make sure you don’t miss an episode.

Also feel free to connect with me with any questions or feedback you might have. You can find me on LinkedIn as Molly Burkhardt, but also feel free to send me an email as well. And last but not least thank you to my Walter center colleagues, Maureen Langley, Camryn Schreiner, Geoff Heck, and Amy Cornell for collaborating on the production of this podcast. Thanks again everyone. And we’ll see you in the Fall for the next season of All Careers Considered!

By Camryn Schreiner
Camryn Schreiner Videography Intern Camryn Schreiner