What We Can Learn from Taylor Swift

AMY GALLO: You are listening to Women at Work from Harvard Business Review. I’m Amy Gallo here with Maureen Hoch, who’s the editor of hbr.org and who has a book recommendation for us.

MAUREEN HOCH: Hi, Amy.

AMY GALLO: Hi Maureen.

MAUREEN HOCH: So my recommendation is a new book from our colleague Kevin Evers, who’s a senior editor here at HBR, and it is called There’s Nothing Like This: The Strategic Genius of Taylor Swift.

AMY GALLO: I have to tell you, I’m very proud to work for an outlet that has published a book about Taylor Swift.

MAUREEN HOCH: I know! And so, here’s a question for you actually.

AMY GALLO: Yeah.

MAUREEN HOCH: What do you know of the strategic genius of Taylor Swift?

AMY GALLO: Well, I have to say, as the mom of a teenager, when I hear Taylor Swift’s name, I get a little disappointed that I didn’t raise a Swifty because I felt like that was going to be my entree into her. So, I haven’t been as much into her music as I want to be, although “Folklore” did get me through some dark pandemic times. But I have been a real keen observer as someone who thinks about women and work and have just always been impressed with her career and how she manages her brand and herself. And of course, it’s hard to miss the controversy and the shade thrown her way, and she just always bounces back and always continues to build this amazing business. So how did you get into Taylor Swift? Is Irene a Swifty?

MARUEEN HOCH: Irene, my daughter—my 10-year-old daughter… I don’t know if she’d call herself a Swifty, but she does have a lot of interest in and admiration for Taylor Swift. And I think one of the things that Taylor does well is she knows how to hit a moment, right?

AMY GALLO: Yes

MAUREEN HOCH: She’s got a really good sense of timing. When she was on SNL and did the 10 minute version of “All Too Well”, I remember sitting… I sat with two friends and watched that. We were just so fascinated by her and the spectacle of it all and she killed it.

AMY GALLO: Well, and Harper, who…my daughter, who’s not a Swifty—made us sit down and watch that with her.

MAUREEN HOCH: Yeah.

AMY GALLO: Yeah. I have to say her strategic genius was really so clarified for me when my mom, who’s almost 80, sometime over the past year during… I think it was toward the end of the Eras Tour, said to me, “do you know who I have a lot of respect for?” And I said, “who, Mom?” And she said, “Taylor Swift.” And I thought, oh man, Taylor is doing something right to be able to reach your 10-year-old daughter to reach us as middle aged woman and to reach my mom. It’s amazing. Tell me.. I haven’t read the book yet, it’s on my list. But tell me what Kevin… how he captures what’s so smart about her approach.

MAUREEN HOCH: So I mean, I like that it wasn’t just a book for somebody who is a fan of Taylor’s. This is a book for anyone who’s interested in successful business strategy. And unless you’ve been literally living under a rock, you have probably seen, been exposed to her fame, the tours, the football games. What is it that actually got her there? This is a good book for that. It’s looking at the decisions she made, pivot points in her career. And I like the fact that Kevin looked at it not just through the genius part of it, but there are hits and misses. Every successful person has ups and downs, has things that go right and wrong. So I appreciated that piece of it too. Yeah.

AMY GALLO: But it is also a book for fans.

MAUREEN HOCH: It is, it is.

AMY GALLO: And we have some big fans in this building at HBR. So you had a conversation with three of our fellow HBR Swifties. Tell us…

MAUREEN HOCH: That is true. It was right in this room and it was with Caitlin Amorin, Courtney Cashman, and Susan Francis. And we sat at this very table and we basically had a mini book club to talk about what we learned from the book and what those insights meant to us, including knowing what your strengths are. I mean, I think knowing what you want and what you don’t want, which is in my opinion, one of the hardest things to know. Pushing forward even when people doubt you, all of those things. Yeah,

AMY GALLO: It sounds like classic Women at Work territory. I love the idea of knowing who you are as a person, but as a business and knowing what your fans slash customers want.

MAUREEN HOCH: Exactly.

AMY GALLO: And her ability to marry those. Okay. I’m super bummed now I wasn’t at the table.

MAUREEN HOCH: You would’ve had fun.

AMY GALLO: I would’ve

MAUREEN HOCH: Next time, but here’s our conversation edited down to the length of my favorite Taylor Swift song “All Too Well (10 Minute Version)”. Caitlin, why don’t you start us off?

CAITLIN AMORIN: So the first time I had ever heard of Taylor Swift was during the Jonas Brothers 3D Concert movie when I was in fifth grade. She came out and sang “Should’ve Said No.” I was like, Oh, I kind of like that girl. And then I remembered that summer Fearless had just come out and “You Belong With Me” came on the radio. “Love Story” came on the radio and my mom started buying me her albums and kind of saying, “Here you go,” because she thought that Taylor was a really great role model. And then the fact that she was bullied in school… I was bullied as well, and I would listen to “The Best Day”… I’m sure you guys will listen to it. That was my mom’s song. And she also cries through that because that talks about the bullying and your parents waiting for you to shine as well and being there for you.

MAUREEN HOCH: How about you, Susan?

SUSAN FRANCIS: So I’ve always been a music person my whole life—all genres accept country. So I knew who she was of course, but was not my cup of tea. But then I went to visit my niece who was, like, five years old, and I was sitting next to her in the car and she’s looking out the window and singing along with such deep feeling about how she got tired of waiting and wondering if you were ever coming around and how her faith in you was fading. It just made me sit up that she was connecting with lyrics and experiences that presumably she hadn’t had yet. But it wasn’t until it came into my house because of a hiring mistake, because I needed a new babysitter for my girls. So I did driving, record, background, check, resume, reference check, all of that. I never thought to ask about babysitters’ favorite genres of music or artists. So our dear Lizzie introduced my kids to country and to Taylor Swift, and they would ask me to tune the radio to country music and play Taylor Swift. So, that was where she came to be in my house,

MAUREEN HOCH: Courtney?

COURTNEY CASHMAN: So mine was also through family. My daughter was four at the time. She’s six now. So I’m very old school in my listening habits, I still listen to the radio. So we’d be in the car and one day she just asked, “Who sings this?” And it was a Taylor Swift song, and the next time we’re in the car, she hears again. She’s like, “who is this?” Taylor Swift. Well, then she started only recognizing songs by Taylor Swift in the car. And then I took her to The Eras movie and she loved it, and she started listening to 1989 every night before bed. Now it’s Lover. But in doing all that with her, I started really enjoying the music much more than I had when I would hear a one-off song on the radio and listening through the whole albums, and I was basically drawn in as well.

CAITLIN AMORIN: One of the things that I’m really enjoying about this conversation is the fact that you all are moms and that you are forming your Taylor Swift fandom through your children. And for me, that was something that I shared and still share with my mom. She was the one that was buying the albums for me. And when 1989 came out, on the release day, I came home and the album was there for me after school. And I went to the 1989 Tour with my mom. And then she didn’t get to come with me to the Eras Tour and I FaceTimed her during “Love Story” because that’s one of her favorite songs, and she was just crying, listening to it. I feel like I hear stories all the time about parents hating their kids’ music and just to have someone that you can connect with and say, Oh yeah, that is someone that I want my child looking up to, I think is so powerful. And the fact that she also transpasses generations I think is really important too.

MAUREEN HOCH: I mean, one thing I really admire about her is knowing who she is, but also just her ambition and willingness to hold out for what she wants. If I relate that to how women function in the workplace, you’re not always encouraged to be super ambitious or you’re constantly feeling like you have to settle in some way. There were a lot of times where she said, no, I don’t want that. I want this. That was inspiring to me.

COURTNEY CASHMAN: Yeah, I was also really impressed with just how well she knew and could tell someone her own strengths. I feel like that’s something that we’re always told to do is to know your strengths, play to your strengths. I’m not sure that I could give you a list of what my strengths are. I’m sure if I thought about it, I could start describing them, but she seemed to just have this way of being like, I am a songwriter, I know what I am doing, I’m good at it, and I’m going to tell these people who have been in the industry for decades that I’m good at it and this is how I’m going to do it. This was back when she was just trying to get a label or she had just signed on with a label. And that’s really impressive—not just for someone that age and new to the business but, as you were saying, Maureen, that’s not exactly something that’s applauded for women either.

SUSAN FRANCIS: And Kevin talks about that too in the book, that even though all along she’s been like, I’m a storyteller and I’m obsessed with my fans, that when she got critiqued for her voice—the quality of her voice… that didn’t always apply to other men and Bob Dylan and Tom Petty and Neil Young. And like, Oh, well, yeah, maybe their voices aren’t great, but they’re storytellers and that’s their value. Where she just gets the criticism without the sort of balance of, Oh, but great story.

COURTNEY CASHMAN: I mean, any sort of celebrity, let alone someone who’s putting themselves out there as much as she is with her songwriting and her authenticity, is going to get negative feedback and not know which is the real negative feedback and which are just people who are haters,

SUSAN FRANCIS: Haters gonna hate.

COURTNEY CASHMAN: Yep, hater’s gonna hate, hate, hate. But she took it and listened. I mean, after people were saying she had a terrible voice, she got vocal coaching and training. She was already a success at that point. She didn’t have to, but she did. And that’s something that Kevin explores in the book. She really did take it to heart and say, Where do I need to improve?

MAUREEN HOCH: What do you think is next for her? What do you hope to see her do?

CAITLIN AMORIN: Do you want my crazy fans theory?

MAUREEN HOCH: Yes!

CAITLIN AMORIN: So I feel like I am very much in the camp of the “Swifties who clown” and who are waiting for Reputation (Taylor’s Version) to come out every other day. So what I think she’s going to do—I’ve noticed a pattern with the re-release of her masters. She releases two per year and then releases another album. So what I think she’s going to do is re-release Reputation to Taylor’s Version and Taylor Swift (Taylor’s Version) this year. She’ll release another album in 2026, and then tour in 2027.

COURTNEY CASHMAN: I do wonder where she might go outside of just music though. Taylor could very well go in the same kind of direction where she starts her own enterprises or maybe she goes behind the scenes where she’s starting to produce other people’s tracks and help them out to help out the next generation of musicians.

CAITLIN AMORIN: Starting her own label is something that I’ve thought about too, because her passion about rights for artists… I could see her starting her own label and basically being like, Here’s the money, you own your masters, I have this platform, I wish I had had it when I was starting, I want to give back. That is a really great example for all women that are in positions of power. We need to be sticking up for people that are beneath us in our organizational structures and standing up for them, advocating for them, helping them find avenues to get to the place that they want to be in their career.

SUSAN FRANCIS: We know she has a plan, right? She has proven to us—and Kevin has captured it—that she always has a plan and she has the vision. And it’s not just what she wants someday, but all the steps that she’s going to take to get there. She just hasn’t let us in on it yet. Or she’s let us in on the game and we just haven’t figured it out yet.

COURTNEY CASHMAN: And I think what you just said, Susan, is what stuck out to me is it’s not just she has a vision, she has the steps she needs to take to get there. And she’s had that…I mean, that was back when she was a teenager. She had the exact same thing. She knew where she wanted to go, but she had the steps how to get there. I think as anyone is thinking about their career, that always feels like the hardest part. I can say I want to be this leader, but you also need to know how to get there. And that’s something that struck me because it’s hard as I’m in my forties. It’s hard as a 40 something. She was doing it at 15.

SUSAN FRANCIS: And not just of knowing what she wants but asking for it. And I’m thinking of the story Kevin tells in the book about how she called in to a radio show when Tim McGraw was being interviewed and was like, Hey Tim, when are you going to start having opening acts and have me be one of them?

MAUREEN HOCH: I’m curious, did your impression of Taylor change at all from reading the book?

COURTNEY CASHMAN: Yeah, I’ll admit to that—probably because I am so new to really learning the details, all she had to do to get where she was. Going back and listening to those songs, I have a newfound respect for them. She has done a lot that she does not get credit for.

CAITLIN AMORIN: So my impression of her actually didn’t change because as a fan, this is all stuff that I was very aware of. I’m just happy that we are recognizing someone who has a phenomenal work ethic, who has not always been celebrated for that

AMY GALLO: You can buy There’s Nothing Like This at store.hbr.org or wherever you like to buy books. And in a recent HBR IdeaCast episode, the book’s author, Kevin Evers, explains what all leaders can learn from Taylor Swift.

KEVIN EVERS: This is a classic entrepreneurial story. She seized an opportunity that other people were ignoring. So let’s go back. She’s 14 years old, 15 years old. She wanted to write her own songs which, at the time, was rare in country music—especially for someone her age. It’s usually done by professional songwriters. And she wanted to write those songs for an audience of her peers—teenage girls. That was a market that executives in country music, based on data and based on past failures, said that market doesn’t exist. But she said, I listen to country music, I’m not hearing songs that talk about my own perspective, my friends are listening to country music. So she was really close to her fan base, her customer base. It’s a classic blue ocean strategy. She went after an audience that people didn’t think existed. And because of that, she found great success because she really didn’t have much competition when she broke through.

AMY GALLO: Find the link to that IdeaCast episode in our show notes. Women At Work’s editorial and production team is Amanda Kersey, Maureen Hoch, Tina Tobey Mack, Hannah Bates, Rob Eckhardt, and Ian Fox. Robin Moore composed the show’s theme music every week. Maureen actually puts out an insider newsletter where she has lots of recommendations. Tell us a little bit about it, Maureen.

MAUREEN HOCH: Sure. So The Insider is just for HBR subscribers, and each week I work with a team of editors to recommend articles, books, podcast, episodes, videos, events that we’re putting on. All of these weekly recommendations are one of the perks of subscribing to Harvard Business Review. So, if you’re not a subscriber yet, please head over to hbr.org/subscribe.

AMY GALLO: I’m Amy Gallo. Get in touch with me and Amy B. by emailing [email protected].