Today’s guest is Sally Singer, creative director at vogue.com. My conversation with her is so fascinating. This is the first one. I’ve split one episode into two parts partly because this is such a new world for me but I believe incredibly valuable for leadership. So the first episode this one is on vogue.com. It’s on storytelling and journalism in general. She’s had a storied career throughout journalism including the New York Times and Vogue now. It’s about fashion. It’s about style. It’s about her meeting Chelsea Manning for the first time as a free woman. It’s also her professional and personal development, her goals and achievement to reach these levels of the fashion world, of the journalism world. You get to hear her passion for these Nigerian [unintelligible]. I’ll get the link. Check it out because they have incredible style and what they’ve shown what Sally reveals about herself and what she’s looking for is very different than I would have expected. Maybe it’s because it’s a world that I’m not so used to, maybe you’re more used to it but I find it fascinating. And style and fashion are not about money. I mean this world is still foreign to me but it’s incredibly influential. Pick a great historical figure, pick someone that you consider important throughout history, I bet he or she had a visual style and more today than ever because of the cameras everywhere and the distribution globally is so easily. So let’s listen to Sally Singer talk about herself, journalism, vogue.com and in the next one we’ll talk more about the environment.

***

Joshua: Welcome to the Leadership and the Environment podcast. This is Joshua Spodek. I’m here with Sally Singer. Sally, how are you doing?

Sally: Fine. How are you?

Joshua: I’m great. We’re in these stunning offices of Vogue. It’s really beautiful here. And sorry, the listeners can’t see it. One of the goals of the podcast is to bring leaders from lots of different areas because there’s so many ways that leadership happens in so many different areas. And fashion I think of as a very… Two things I think about fashion. One, I don’t think of myself as a particularly… I don’t think it is my field so I’m kind of out of my element here. But also, it’s a very influential field and I feel like it’s a really big deal that you know in the environment people have constantly gone to science. I think science and academia is where people have gone for leadership and I think that it’s missing a lot of leadership from a lot of different… Did you read the story in The Sunday Times this week by any chance in the…? The Sunday magazine had one really long story on how in the decade between…

Sally: Oh, I haven’t read it yet. I put it aside to read on a trip I have to go on this weekend. I did see that about how we’ve fallen behind in an our… We were making pace towards righting the wrongs in the environment and how it all rolled moving backwards now. Isn’t it something like that?

Joshua: Something like that.

Sally: Yeah, yeah.

Joshua: And when I looked at it, it had a lot of scientists and not really politicians working on the stuff and I don’t think they were leading very effectively. So I want to get to, one, you as an individual have been in many leadership roles and have led many people, and then this field is very influential. And I feel like it’s both of these things are missing from environmental leadership. I want to get there by way of learning more about you actually if that’s OK because you are the creative director here at vogue.com. Of all digital?

Sally: I am a creative director of digital for Vogue, yeah, the brand which encompasses vogue.com, our social channels, our YouTube and video channels. All of the digital incarnations of the brand.

Joshua: So my understanding that’s roughly on par with print. I mean it was once only print and now it’s not.

Sally: It’s not a part. It’s you know the print edition of Vogue is one incarnation of it and in digital we have many incarnations of the brand. They’re all different. They’re all unique. They share some content across all platforms. And then there’s always platform specific content. But we have a vast global reach in digital the brand which is nice.

Joshua: And you’ve spent a long time at Vogue. You were at the New York Times, at the Style magazine, London Review of Books. It seems like a lot of different things but maybe that’s from the outside.

Sally: Well, I mean I’ve been in American Vogue for a significant portion of my life actually and I was at British Vogue before American Vogue for a period. So there is some consistency there. I don’t hopper on that much but I have in my time in fashion been fashion director of New York Magazine, style director of Elle magazine, editor in chief of [unintelligible] for the New York Times. And that’s probably it for my fashion life. And then before that I worked in book publishing. I worked Farrar, Straus and Giroux which is a New York based book publisher. I have a division called Hill and Wang which is more academic part of the company. I worked for Verso and [unintelligible] Review. And I worked for the London Review of Books. So you know I’ve had a career in two parts I guess.

Joshua: When I think of people in journalism or in print or I think of storytelling is what they do but… How would you… What’s your passion behind driving all this?

Sally: Oh, I do think storytelling is what I do and is what motivates me to get up in the morning, go to work and is the essence of everything we do now in digital at vogue.com. I think you know storytelling when you’re in print is rather… Though it’s kind of obvious what the manifestations of those stories are – there’s text and there’s a visual to go with it, either an illustration or pictures. Storytelling online can take any form – it can be audio, it can be video, it can be a gif, it can be a tweet, it can be a text story, it can be a slide show, it can be a mystical, it can be a cinema graph. I mean there’s so many ways to tell stories when you have all of the digital tools in front of you.

So for me the ability to if not tell stories, to edit stories other people are telling has just increased exponentially by working in digital. It’s for me far more exciting than when we only had the printed world. But I still work on print as well. So I do [unintelligible] print and I do the print, I love printed magazines and printed newspapers so I still actually contribute to the print publication as well.

Joshua: You said it was exciting and actually I was going to ask you is it… Because I could imagine it could be daunting, it could be anxiety causing…

Sally: All those things do. Yeah, exhausting but it’s fun. If you like to tell stories, there are so many ways to tell stories now and there’s so many people telling stories because the tools of media are available to everyone now. Everyone can be a journalist, everyone can report on their world, everyone can narrate their life and they can gain you know scale and a global audience from it. It’s kind of good. It’s an interesting time.

Joshua: I feel like partly you’re saying that it’s like encouraging anyone listening with, “You can do this. You can do.”

Sally: Yeah, sure. Of course, you can. I mean even here at Vogue, at vogue.com I like working with user generated content and editing it into video and doing collaborative work with people around the world. We do quite a bit of it now. And, yeah, it’s fun. It’s really fun.

Joshua: When you said we do quite a bit of it now the “now” implied that there’s been some change… You’ve been in this role for five-six years.

Sally: I want to say probably about five years now. I think we’re doing…We’ve worked with UGC content a bit over the course of the years but in the last year or so as we’ve built out these features we called Vouge world we published one grid of 100 people in February. We have another one coming up soon in the fall. We work with collaborators all over the world to sort of help them tell their stories through our site. And I am in the midst of editing a lot of people’s content right now and it’s really fun. And you know we send people sizzle reels and things we’ve modeled out of how we think a story can be told and they send in their version of it and it’s very collaborative and you end up with something that’s greater than the sum of any of the parts. I find it very rewarding.

Joshua: Yeah, the listeners can’t see your face. I am seeing like you’re not faking it, like you have this look of maybe a child playing with toys or like this is really like…

Sally: Well, it’s just super cool. Like just yesterday I was looking at a video we’ve just helped two young men in Nigeria who have incredible style and they document their world and I mean they have street style where there is no street. There’s no street where they live like… There’s no street that you would identify as a street. And they dress incredibly and they customize everything and are customizing things with feathers or customizing things with anything they can find with you know buttons and beads and whatever is left and it’s just brilliant. It’s like what they’re making is brilliant and the way they look is brilliant and I think that’s street style. That is really something.

Joshua: How were they able to reach you? Is it easy to reach you?

Sally: We found them somewhere. Someone who likes what they did. One of the women who worked with me I think had seen their… She travels extensively in Africa, had seen something and put it together that you know they’re customizers of things. So they’re designers of a sort and hooked us up. Someone always finds people. People have style. You just find them. We just find them. They find us. We find them. It’s fun.

Joshua: It’s funny, you made me think of when I played sports when I played Ultimate Frisbee, an odd sport not played by many people but a really intense sport. And one time I was walking around in Southeast Asia, I don’t know where it was, I just saw someone, I was like, “Do you play Ultimate?” He said, “I do.” And suddenly I connected to this whole community there and I guess style has that too or I don’t know if I am misusing style, fashion, these different terms.

Sally: I mean I think you can if you have people with the right and tan eye around you and looking for the right things. I mean I think that but it is… There’s never been a better time. If you’re interested in expressing yourself visually through fashion to be or because you can put yourself out there on Instagram and you can be a star in your own road and you can explain it to the world, you can explain it in text, you can explain it in video, I mean you can explain yourself to the world. And if it’s interesting, the world will probably find you and will watch. And that is just new. That’s just in the last few years. It just didn’t exist. So we don’t find everyone through Instagram because I like whenever we’re working with you know really new people we find talented around the world or we find interesting around the world I like a mix between people who have substantial followings which would be the normal calculated way you go out because you know people like to work with influencers and influencers are people who have followings so that you bring new eyeballs to what you do. It’s kind of a pariahish way of being.

Sometimes you like people who have big followings because they’re good at telling stories and a lot of people watch them and it’s exciting. That’s part of the deal. And sometimes you like people who aren’t on social media at all because you know they’re interesting. They’re just as interesting, they just don’t have any social media for themselves that’s not where they put their energy. Doesn’t mean that it doesn’t work for me, it doesn’t mean that it won’t work on our social media. We will introduce them to people in that way. So I think always with and I emphasize this with my team when we are talent spotting and you know keeping our eyes and ears open, we’ve got to keep our eyes and ears open everywhere, not just on Instagram or a platform that’s already established because that recognizes some people’s aspirations. It doesn’t recognize the whole world’s aspirations.

Joshua: From where I am when I see…Like everyone seems so well-dressed and so well made up and all this stuff. Because I don’t even know like my experience with Vogue is generally something like I’ll pick it up and kind of leave through…

Sally: The printed magazine. Well, I mean the printed magazine Vogue is a polished experience. It has to be. I mean those pictures are beautifully made, they are made with care, they’re made with time, they’re constructed, beautiful constructed images. That’s what a print magazine has even the most spontaneous ones and the ones done with photojournalists and you know Vogue’s been working with some photojournalists recently and with younger and newer photographers who work in a more spontaneous way. But even then, you know the construction of a print image there should be care. It’s not a happy snap. It’s not meant to live on Tumblr. It’s meant to live in print. It’s meant to possibly go on a wall of a museum at some point. So those images have to be done with care. And so in that sense anything done with care is going to be you know it’s going to have a beauty to it even if it’s not you know striving for beauty in a conventional sense.

Joshua: So the way you describe it it makes it sound a lot more accessible than I would have thought. I mean what you were describing before it sounds like…

Sally: I mean what I was talking about with vogue.com and influencers and people we find interesting?

Joshua: That even more so. But even what you just said about the printed version even though you’re saying it’s done with care and it might end up I guess every single one, not every single one, but a lot of them are probably like this could end up on a museum wall someday. Even when you put it that way I wonder why, not exactly why, but I feel like the way you’re describing it makes it seem more accessible. Now what you talked about vogue.com is way even more so because it seems like the opposite of elite. You’re trying to find what is out there who’s expressed themselves and how and you know you’re not trying to keep people out. You’re trying to bring people in.

***

Sally: Yeah, I mean I guess my experience of Vogue and my interpretation of Vogue which is mine, I’m just speaking for myself, I’m not speaking for the brand or my boss or anything. I mean I’ve always seen Vogue as a kind of well, I guess growing up. I always saw Vogue like getting a letter from that friend I would never have once a month that was going to tell me all these things that I didn’t have any other access to except to the pages of this thing that arrived in the mail once a month when I was a subscriber even as a child.

And I don’t think I saw that as an elite friend. I think I saw it as an astonishing friend, just amazing like you know things I would get to look at that I would never have had access to look at in my life or people I would never know. But then all of the propositions, aesthetic propositions that were inside that magazine like all of the cues for fashion I would just consider for my own life and infuse into the things that I sought for myself or reworked from the goodwill or anything like that. They were just directions. I never thought I would have the thing that was in the magazine, nor did I probably want that thing. But I wanted that feeling.

So you know if everything was kind of shimmery and bugle beaded and you know Minnie if I remember correctly there was some period maybe when I wasn’t trying to figure out my prom dress I would make a shimmery short dress for myself and it would be my version of what was in Vogue. I always thought of Vogue as a set of ideas that I could incorporate into my life and into in my own life I never… I didn’t register it as elite, as in you know elite as a walled off from my experience. I viewed it on a continuum to my experience but it was going to be my interpretation of it and I guess I still see it that way. And I’ve seen it that way and all the time I’ve worked for it. And again, I do think that the printed version, the printed incarnation of Vogue is highly, highly edited because it’s only even though it’s very fat it’s only [unintelligible] big and the world is massive. But you can only tell so many stories a month in it and those stories are really thought out. Every aspect of them is completely thought out. You can’t just you know throw someone in for the hell of it.

So in the mix of stories, in the mix of people who are profiled, in the mix of models who appear in the pages and celebrities who appear in the pages it kind of has to be the most interesting of the most interesting, the best of the best, the most beautiful of the most beautiful, the most kind of provocative of provocative, whatever it’s going to be it’s going to be that and then once someone is going to make the pages of Vogue a subject to selected the treatment of them visually has to be extraordinary. Now whether it accords with one’s idea of beauty I don’t know. But it has to be extraordinary so that can mean… And it has to be as well not mocking tabloid humorous odd for the sake of being odd. It has to be respectful, inspiring… Every reason we put that person in there which is because we’re really interested in them has to come out in that picture.

I’m thinking of a picture we did this year of… Actually, it was probably 2017-2018 of Chelsea Manning when Chelsea was released from prison in Kansas and she came to New York and she was shot by Annie Leibovitz and Phyllis Posner for the print edition of Vogue and it was on a beach in a red swimsuit because Chelsea loves to swim. I don’t know if you saw it. I mean it’s an incredibly beautiful and strong picture of Chelsea Manning. It’s not a fashion picture. It’s not positing herds of fashion person. The choice [unintelligible] is literally because that is what Chelsea most want to do when she got out of prison was to swim. That was her goal was that she could finally swim again and that was important to her. And I think Chelsea Manning is someone that we thought was worthy, interesting for some of us you know important. And but that’s not elite. That’s not an elite story. But we you know had a profile of her the New York Times Magazine did so it was elite in the sense of only two places where she was going to give interviews to and one TV news outlet I think as well, maybe ABC or something. So she wasn’t going to do press everywhere. So it’s an elite experience to get to work with her. But is that an elite story? I don’t know. Not to a lot of people. Right? It’s not probably your idea when you say you think of Vogue is a beautiful world of just elite people, that’s probably not a story that would come to mind. But that’s one of the most important stories we did last year in my view.

Joshua: Yeah, I don’t know how it is registering on my face but what I’m hearing now I wish I’d had a long time before because it would give me… One, I’m going to listen to what you’re saying many times and two, I’m going to re-look at Vogue in a new way. It reminds me of… I don’t know if this is similar, different, but years ago I was on a long car trip and someone in the car was… He taught film at NYU in Columbia and we’re going around like what’s your favorite movie. And he started talking about the French New Wave and I had no idea about the French New Wave. I didn’t know about the studio system before and how it changed everything. What made it happen was… When it came to his turn like what’s your favorite movie he said, “American movies of the 60s and 70s.” And everyone else in the car was on a road trip and we were like, “What does that mean? Why that?” And he talked about how the studio system, the director was just kind of like an employee and a big Cast of Thousands. And people started not going to see them anymore because it was just big Cast of Thousands. And the French New Wave was very personal and they did what they could. And when I went back and watched Godard and Truffaut and Rene and I was like Wow! And then I re-watched like Easy Rider and Harold and Maude and the movie’s run then Graduate. What was the other one? I am trying to think of. Anyway. And I was like, “Oh, now I see an American take on this thing. Really opened up a whole new world for me.” And the way you’re talking feels like there’s something in fashion or a lot of things in fashion that I was just kind of like well, that stuff is over. I don’t really know.

Sally: Well, I mean why would you? I mean this is just one story of many stories that probably I mean… You know this is one of many stories that could easily slip by one in the media times you live in which I feel you know fully saturated.

For me what was another interesting side note to the Chelsea Manning story for us is that when Chelsea was released from prison, myself and a colleague of mine here and friend Jordan [unintelligible] put together the clothes that were sent to the prison. So when she got out she could dress as a woman because when she had entered prison she had not transitioned yet. She entered prison as a man, as Bradley Manning. And we knew that when she came out, she wouldn’t have anything to wear. And so we put together a care package of clothes that were donated from friends and donated from our closets and sent it to her and then she came to New York and she came to where I then lived which was the Chelsea Hotel and my neighbor Niall [unintelligible] was amazing tailor, did all of like Sex and the City clothes and all of Sarah Jessica Parker clothes like one of the best of the best of the best, tailored all these clothes that we had put together for her. We gave her some clothes to wear like a wardrobe and then I went shopping with her a couple of times to like some vintage stores to help her… And she had very specific ideas of what she wanted to wear and what her look so you didn’t have to help her construct a look, just had to maybe help assemble the parts.

And for me that was totally separate to what was happening with the print magazine and that print story was a totally separate operation done out of the website. But in conjunction we were trying to just with the resources we have help someone feel comfortable in the world when the world was not going to be a very comfortable place, just for a while. Go into prison is one thing, come out of it as celebrity who stands for a lot of things to a lot of people. And you’re going to walk the streets for the first time really as a woman. And that is something that most women have spent their whole lives negotiating and have some comfort or discomfort with it but no other way around it. And how do you help someone do that? How do you just make that easier? Like how do you give someone the mental freedom to blend in, to not stand out, to stand out when they want to stand out, to you know feel at ease in a world that’s not a world filled with ease for anyone but especially not for someone coming out as famous and infamous to some people.

And so that was a project that was done through the auspices of well Vogue or vogue.com maybe what I wrote about it on site I did a story with her and Nathan how he did a brilliant, brilliant piece in the print magazine. We did a second smaller story outside about her fashion sense and dressing her and the like.

And you know those are things that I don’t think people necessarily ascribe to being part of Vogue. But it is part of the power of Vogue that you can think that hard about what it means to get dressed in the morning and what it means to be a woman and be dressed that way in the morning. So that’s the Vogue that I work for. There might be a lot other Vogues and there might be a really elite idea, but the Vogue that I work for does that. That is what I do. And that is what we do. So when we’re working with people in Nigeria to make videos about the way they dress, I want to know why they dress that way, why they get up in the world and dress that way. That’s what Vogue should do.

Joshua: You said that you can do that. From you it sounds like almost your responsibility…

Sally: That’s what makes coming to work exciting, makes it interesting. And that’s the whole point. People get dressed up in the morning and they create themselves. Designers get up in the morning and figure out ways that they think the world should look for a time, for a short time, not forever but like for two months – three months. And that right now a fashion season is about a month that’s what because their shows every fricking month. But you know for a season whatever the season now is or that mid-season or the half-season designers wake up and they have to create and express the propositions for how people should look on the streets. That is interesting. And also, your own sense of what that should be next and how can you create the idea that that’s the way the world should look next and what does that mean. It’s fun.

Joshua: My idea of self-expression is so rooted in printed words, spoken word and not so much the visual…

Sally: [unintelligible] every day.

Joshua: Yeah. And well, OK. I mean for a long time it was just jeans and a T-shirt and it’s often very functional. The way I hear you talking makes me more in tune to it. It’s outside my realm and also part of the reason I’m here is that I feel like as I was saying before I think a core part of leading effectively is to express yourself authentically, express yourself genuinely, to be aware of what you have to express. And I feel like that’s something that’s missing a lot in the scientific talk and the doom and gloom talk that… There’s part of me that says, “Josh, you don’t know what you’re doing over at Vogue, vogue.com. It’s out of your element.” Pardon me. Correct me if I’m wrong, this is a very influential business. This is a very influential not just this business but…

Sally: Fashion?

Joshua: Yeah.

Sally: Or media? What side of…

Joshua: Yeah. From any perspective I mean fashion, media, journalism.

Sally: Well, actually I mean fashion, media they both influence businesses in different ways, I guess, so many different ways.

***

If you had asked me before this episode what area I would split the first interview into two parts because I found it so fascinating, I doubt I would have guessed fashion or style. Now having listened to it I’m not so surprised. Partly it’s because my inexperience and my ignorance of the field. Almost no one in fashion I see acting environmentally at the level that they could and almost no one in the environmental world is acting with an engaging style whereas great leaders throughout history consistently have a visual style that’s remarkable and memorable.

And listening to her it’s about something much more deep than what you see on the surface. It’s about self-expression. It’s about stories. It’s about people at the foundation and that’s what leadership is about. So this episode was educational for me. Since she shared that depth and how personal it was beyond what I think outsiders would’ve expected at least me. So I think I saw this area short but I think it’s totally missing from environmental activity yet it’s critical for leadership. There’s still the second half of my first conversation with Sally in which we talked about the environment and her personal commitment to act on her environmental values. So stay tuned for part two of episode one.

• ← 128: Sally Singer: Fashion and the Environment
• 129: Dave Gardner, part 2: “Came to relieve the burden, stayed for the joy” (transcript) →