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Ego wise, it is really hard to go from being like the expert of the experts to the novice of the novices, and I have to just swallow that and show up as the person who is really curious welcomed in her shoes.

I'm Izzy Greenspan, deputy style editor at The Cut, and in this podcast we talk to ambitious women about how they've come this far and where they're going next.

When I started thinking about talking to Iacone and I thought I would be interviewing the editor in chief of Marie Claire, I has been a fashion editor for nearly 20 years.

She worked at Teen Vogue. When it first launched, she was fashion director at Nylon Cosmopolitan 17. She was chief fashion director at Hearst. She styled countless celebrities and worked on fashion ads. She also just has this incredibly fun, authentic social media presence. And she has a young daughter. And I was excited to talk to her about fashion, being a working mom, how to make a magazine in the age of Zoom.

But what I didn't know is that I was about to leave Marie Claire for a new role as head of content and editorial partnerships at Pinterest, which, of course, spun our conversation in a whole other direction. What's it like to change careers, to change industries in a year that's already consumed with constant change? How do you know when it's a good time to take a risk? I also just wanted to talk to her about making a life on social media, and she had really interesting things to say about FAMO being creative on the Internet and where she wants to take Pinterest from here.

Listen for our conversation. Thank you again for joining us. Oh, thank you. Like everyone, I love New York magazine and the cuts, so I'm super glad to be here.

Oh, and you were a fashion intern, right? At one point in your magazine? I was a fashion intern in college, so probably in the year 2000, I was a fashion intern there and it was in the old building and I was one of a handful of fashion interns. So I did like a little bit of everything and worked on photo shoots, did fashion credits and basically was a run around do everything type of person.

So I guess actually, since we're starting down this road, let me ask you to kick things off just a little bit of like kind of your background.

You're a native New Yorker, right? Yes.

So I was born and raised in New York City. My parents came to America from Japan in the late 60s. And interestingly, they actually met in New York. They were set up by mutual friends, you know. Oh, I know someone who is also living in New York City. My father was going to graduate school here at Pratt. My mother also had a short career in magazines as well. She worked at Harper's Bazaar and Vogue. So they both have had very creative lives and creative careers.

So I have been incredibly lucky in my adult life when I look back on my childhood to see that I grew up around people who lived creative lives and really express themselves through their careers and not as like a separate entity tagged on to their careers.

You know, I was looking at sort of your career trajectory and it it seems like, you know, that was obviously such a good colleague, Teen Vogue was when it launched. That was such an amazing moment. But it must have felt like just as totally new thing and this total sort of risk. So I wanted to talk a little bit about, like the power of instinct in your career choices and how you assess when a risk is worth it or not.

Yes, because of the very public nature of my career, I often have people in young women and men in my dreams asking me like, how can I get your sort of career? And I think that a lot of it, as you're saying, has to do with an instinct and also, frankly, just being in the right place at the right time. I was at a moment in my young career where I knew I wanted to make a change.

And I applied for this job at Teen Vogue, which was a brand new startup within Condé Nast. And I interestingly, have found myself in startup environments within larger companies, coincidentally, several times in my career at the time when we started Teen Vogue, it was a very small staff and I was a fashion assistant, which, for those of you that don't know, basically means that you are like the catch all do everything person in the fashion team when it comes to requesting the clothes or making sure the editors have what they need, packing trunks.

It's like a very like sort of manual labor type of job because you're constantly running around. And I I loved it. I mean, I look back on that time in my life and I was genuinely working about seven days a week because on the weekdays I'd be in the office prepping for all these photo shoots. And then on the weekend, I would request to be the assistant on set to help out on those photo shoots so I could see what was going on.

The incredible thing that was happening at that time was that the Vogue editors were styling the photo shoots for Teen Vogue. And so I was able to see these. Pros work and put together this creative concept that hadn't existed before. So, yes, I was extremely lucky. There is no formula that got me there at that time. Once I was there, I definitely seized the opportunity and like squeezed every bit of juice out of the moments. I had to observe different professionals in their element.

But it was lucky.

Yeah, I think also being in that the startup within the big company place is so it's such a sweet spot because you get some of the resources of the big company, but you also get to be really experimental.

Yes, I mean, it was so hilarious because of course one of my jobs was to call up the PR firms and request clothes for photo shoots. And at that time we were still faxing and doing it on the telephone. And there were times when PR firms would be like Teen Vogue. That's not a thing. And like, hang up on me. Yeah, because we were launching the product.

And so they thought that I was lying like, you know, it was such an interesting time. And of course, it's become such a great brand and it still makes me proud all the time to see how it's grown and evolved so much.

Yeah, I remember maybe I'm remembering this wrong, but I remember some skepticism at the time of like, oh, vogue, it's so sophisticated.

Why would there be a teen version? And then it came out and kind of blew everyone away because that's sort of my memory of it.

What I saw as an assistant were stylists like doing incredible work, and that was the kind of creativity that genuinely got me so excited to become a stylist myself. And so when I had the opportunity to go to nylon, which was like another small startup company, I was able to also like rise up in those ranks really quickly because I was the person that was like willing to do anything, willing to participate in any photo shoot just to get the experience.

And that's when I started doing celebrity styling and a lot of that kind of work, which is a completely different sort of headspace.

Right. Let's talk a little bit about celebrity styling. I would love to hear a bit about what you learned working with celebrities and if you ever had any, like, you know, of those sort of fantastical celebrity moments on a set or anything like that.

Yeah. At Nylon, we were shooting a cover with Ashley Olsen. She, as we all know, has a really specific personal style. And so I had been talking to her team at it in advance to make sure that I was gathering the right kind of look, actually to keep it in the vein of what nylon is. But, of course, to make sure that she was happy with what the clothes were. And on the day of the shoot, she, like, showed up.

And she and I were talking about the clothes and she took these t shirts out of her handbag. And she was like, I'm I'm thinking of starting a fashion line. And the first thing we're making is these t shirts. Do you think that maybe if you like them, we can use them in the photo shoot? And there were these like gorgeous like that t shirt, you know, that t shirt in your closet that's just like that perfect t shirt.

You wish you could just clone it and fill your entire closet with perfect, soft, like, beautifully cut t shirts. And of course, the tag inside said the row, and that was her first item that she wanted to launch. That's really cool.

Of course, at the time it was a T-shirt brand and she and I were talking about what her brand would be, which of course has become such a force in the fashion industry. And it was amazing to be with her at that time where she was just thinking about it.

A lot of my best moments with celebrities were when we would have the opportunity to take them outside of their comfort zone. And one time when we were shooting Sienna Miller in London and so myself and my team, we had like basically zero budget to pull this suit off. So like we made a deal with like the hotel, like, hey, if you help us for this photo shoot, it means, you know, amazing Sienna Miller is going to come and and be in the hotel.

So they gave us like basically an entire wing of the hotel to shoot in. And I kind of I gave us the space to, like, really pull this thing off. And it ended up being like we just, like, partied in the hotel. You know, we were all so young, Sienna also. We were all just so young. And I look back on that day as just a day where we had so much fun, partied in the hotel like, had fun with clothes and took pictures.

And the photographs really reflect that vibe where she felt safe to just like, let loose and have fun. And the whole environment of people were there to to make sure that everyone was having a good time. And it was just like, you know, one of those moments that I look back. John, really fondly, another one, and maybe this is probably enough, is Michelle Williams. When we were shooting her, she had a young daughter at the time and her daughter was just on set all day because she was like a young toddler at the time.

And it was great because you could see that it made Michelle so happy to like have her family there.

And because of that, even though we were in like a studio in New York City doing these pictures, the fact that her daughter was there made her so like relaxed in the pictures and so much more like natural and like happy to be there because she was able to, you know, have the most important member of her family there.

That Sienna Miller story. It's like living the dream, right? Like this is the fantasy of working in fashion and getting to just have a good time and create beautiful things. Yes.

I mean, it's only a very few occasions when the fantasy of fashion actually comes to life. And definitely that was one of them.

Right. And that's the thing. You're working potentially, at least as an assistant starting out. You're maybe working seven days a week and you're spending so much time thinking about logistics and shipping and the stuff that is like very much not partying with Sienna Miller. Did you feel you felt that the trade off was worth it? Obviously.

You know, it's interesting because I was in my 20s and frankly, for most of my 30s as well, like so focused on doing the most in my career. And that is evidenced by the fact that I paid no attention to everything else in my life, which is having a personal life. And so, yes, I was able to advance my career in a big way and work with incredible people and travel around the world and all of that. But what I realized as I got a little bit older was that I was living a bit of an imbalanced life and I wasn't paying enough attention to making sure that I had my own existence outside of my job.

Right. So what did you do when you realized that, yeah, when I realized that I was doing online dating and feeling really weird about that, and then I frankly, again, got very lucky and met my now husband. The the process of, like, meeting him and getting married is like its own podcast. But at the time, I think that I was ready to meet someone who also wanted to have a relationship. And after several years of dating, we ended up getting married.

And now we have a beautiful daughter and she's.

How old is she? She's two, right? Yeah, two and a half. Two and a half. Awesome. How do you feel? Like becoming a mom has. This is a huge question, but how has that changed your life?

Becoming a parent changed my life in so infinity ways that it's really hard to describe. But I think as it pertains to my work, I really started thinking about what what is the contribution that I'm making in my creative and career world and how will that be reflected in the world that she grows up in? I had several years of fertility struggles because I, you know, got married later and started trying to have a family later. And so I tried really hard to become a mom.

I tried really hard. I spent a lot of money. I did a lot of things that, you know, made it clear to me that, like, this was something I really wanted. It wasn't like I accidentally became a parent. I very intentionally became a parent.

And so what is, you know, interesting about how your your vision changes when you become a parent is that you start thinking about what is the world that you are creating and giving to them. So I think that's probably the thing that has changed for me the most.

I wonder also in terms of work, you know, you were talking about having it be your entire life and obviously traveling and everything. And of course, you can't do that when you have a family in the same way. Do you feel like it's impacted or changed the way you work creatively to have it be something your that isn't something you're immersed in all of the time, but something that is like, you know, I still like you're sharing the focus with another thing that's incredibly important to you.

Yes, I think that because I became a parent later in my life, that I kind of always have a sense of appreciation for how important this role is to me. But on the other side, if I were to be totally honest, I've been a person who's like all in on my career, my entire life, her adult life. So I don't know how to, like, turn off that muscle.

Like, I I'm still equally passionate about making sure that I am, you know, making the best contribution that I can in my career. So really, it's more just kind of like and there's just more on my plate rather than removing stuff from. Yeah.

And I ask just because I feel the same way that I want to be 100 percent at everything. And it's and in some ways it feels like you just do you just somehow are you have more the pie just gets bigger as opposed to getting sliced. Yes.

And I think like one of the really crazy things about starting a new career and switching industries like which I did recently, is that I spent almost 20 years as a as an editor rising up through the ranks and then ultimately becoming an editor in chief. And your expertise in the media and publishing industry just kind of grows as you climb that ladder and naturally becoming edited. And an editor in chief, you are learning a lot, but you're still an expert in the in the publishing and media space.

You're able to make decisions and know what meetings are important for you to be in and what ones, of course, you should delegate to other people, like, you know, how the puzzle pieces fit together, whereas switching industries, I knew that this would be hard. But now that I'm in the process of doing it and, you know, almost one month into a new job, it's really hard to come into a new industry where genuinely even the words like we're all speaking English, but there are times when I need a glossary to understand what are we talking about?

And I genuinely have a glossary that's like open as a tab on my computer at all times just to be like, oh, wait, what was that term that we're talking about? And so that I can make sure that I'm like learning as quickly as I can in order to then be able to make the contribution of my expertise.

Right. That makes a lot of sense. Change is always hard, but sort of how do you move through it? Oh, my God. Well, I don't know, because I am currently moving, I'm like in the swamp of change right now. So, you know, that I, I don't necessarily have, like, the best words to articulate what I am going through right now. I want to be the right amount of driving hard on myself to always be, you know, squeezing the most out of every moment.

But then I also want to give myself a little bit of permission and time to get used to a brand new environment. So, frankly, all day is a ping pong between those two feelings, because, you know, I have now transferred from the the media and publishing world to the consumer technology space at Pinterest. And the the landscape itself is very, very different. The kinds of departments that had their departments with hundreds of people in them that I'm like, what is that?

What do you do? I'm not devaluing what they do. I'm genuinely like, what is it? Help me understand. Right.

And it's so I feel like you go through that process when you have at least my experience. When you learn about the fashion industry. I feel like so many times in my career I've had to explain to someone outside of the fashion industry something like what a market editor is, that you're so natural to us.

Yes, every industry has so much coded language and so much inside baseball. Priorities that make sense, like exclusively to the people that work there, because the people that experience our product, whether it's the Cut or New York Magazine or Pinterest or Marie Claire or whatever these properties are, have no visibility to the many layers that go into bringing that product to life. And they shouldn't they should just enjoy it and they should be able to to get what they want out of it.

But we as the makers, you know, there's a lot more behind it.

I know you're totally in the middle of this, so I don't feel like we need to do like a follow up in two years when you've got all the accumulated wisdom.

But how do you cope with knowing that you're coming in in a position of authority and you have all this deep knowledge, but it's also like a totally new culture. Are you do you sort of. Front load your like I need to learn Naess or do you want to, like, not be so public about it, like how do you how do you juggle that?

Or I mean, this is like, you know, that time of the night where you're just like staring at the ceiling, like thinking about your day. This is like you're definitely touching on the main thing that I use that time for, which is that I. Want to be extremely respectful of everyone else's knowledge and be in this information gathering space, and luckily I am working at a new company where the people that I have met are so friendly and are so willing to, you know, kind of like bring what they do back to dial it down to zero and like, help me understand from the beginning so that I can in the future make the best contribution that I can.

That said, ego wise, it is really hard to go from being like the expert of the experts to the novice of the novices. And I have to just. Swallow that and show up as the person who is really curious and know that this is a journey, the projects that we have going and the projects that we want to achieve at Pinterest are, you know, these are multi-year projects and consumer technology is constantly changing. And to think that there is some sort of rulebook or playbook that is out there to help me know.

OK, here. Step one. Step two, it just doesn't exist. And so I have to be able to learn as much as I can to start formulating my own strategy and opinions and of course, leading our team in the best possible way. I don't know if that's the best answer to that, but it is genuinely hard. And I think that a lot of people, you know, women and men this year are experiencing career changes. And I know how lucky I am to be a person who is able to make contributions and a lot of a lot of different industries and to be changing industries at this time.

But the day to day of it is definitely it's humbling. It's really hard. And I know I will come out on the other side more fully developed human.

Yeah, but you're doing this in the middle of a time of incredible social change anyway. And that must be hard to sort of change on top of change. On top of change. Yes.

I mean, and I also think that work from home, which we are all experiencing right now, is adds another layer onto it. Because, you know, you and I, if you and I are colleagues, like, I can't just, like, sit down and have a coffee with you and like, you know, form that relationship. We have to like book a time. And we have got a 30 minute slot and it's all in a video call.

And that's, you know, once we come into this time next year of having done that. For, you know, a year and a half of of being work from home colleagues. It'll be interesting to see what our relationships are like, yeah. Do you have and it's totally the answer might be no, but do you have any advice about how to forge a new relationship over or build a better working relationship over Zoom and Slack and all of these things that we have that are like not quite the real thing?

I have found it to be helpful, to be really transparent about everything that you and I just discussed, which is to say that I think that historically people in leadership would really put on a more guarded, stoic facade and that that that idea, that leadership means that you're you're meant to appear like you have it all figured out at all times, is a it's not for me.

And I actually don't think since since you and I, if you we are colleagues, really can't meet in person for a long time. I would rather have us in our limited time on video calls to relate like people and for me to be able to share what's concerning me and what makes me feel insecure and for you to then feel the same way. I think that because I'm coming in from a different industry and that aspect adds a heightened sense to my coming into this this platform world, this consumer technology platform world.

I think that being able to show that vulnerability allows me to create better relationships. But again, I'll tell you in a year, because who knows?

Yeah, I think it's it's hard to do that now. I feel like in a way, some of the. Events of the year have just kind of stripped away that kind of workplace formality, at least in my experience, and it's hard when you're like if your child is popping up and you're assumed to be like, oh, I'm the big boss, like, in a way that feels like you're putting on a front, at least in my experience.

Can I ask you a little bit about authenticity and vulnerability? It's one of the things that I think really stands out in your social media presence that you feel it always just feels so like really charmingly authentic to me. But that also does mean opening yourself up to, like, weird Internet criticism and and being in a place of vulnerability. So I'm curious about how that feels to you and the way that you think about that.

I you know, because I am not a whatever they call it, digital native and I am part of that generation. I think they're called zinnias, who are people who grew up without technology but have been using it their entire adult life. I have historically taken all these tools sort of at face value, and it's not something that feels normal to me. But I also do know that when I am able to behave in a more open way, whether it's with you on a video call or on my own social media platforms or, you know, in the workplace and at home, that that everyone in the relationship benefits.

And luckily, I think that that's the the general consensus of everyone in the the social media platform space, is that presenting a perfect life isn't what anyone wants anymore. And maybe in the beginning of using some of these tools, you would like create your aesthetic to perfection. It's just like nobody wants to see that anymore because nobody lives that way. And then also, I think that becoming a parent definitely, you know, I feel like I am recording a journal for.

A lot of people to see, but actually when I'm making it, I'm thinking of it as something that I want my kid to one day be able to look at of like this is what was happening in August of twenty twenty when I was a two year old. And this is what my mom looked like and this is what she was thinking.

So if you put on that mindset, actually, you you address everything in your life differently. I love that.

I've never thought about that before. But to have your primary audience be your daughter when she's grown up, that's really, really cool.

So let me ask you a little bit about Pinterest and your plans and what you know, what you're what you've going to do. So one of the things after becoming a parent that I started thinking about a lot is the idea of what how is this world of media changing and what's the best way for me to make a positive contribution to the future of media, the future of publishing, the future of how people create and express ideas in the world. And so when I became an editor in chief, that was an incredible opportunity to be able to shape a brand, which is, of course, like a print magazine, a website and an experiential platform.

All that 360 of the brand was something that was a really like ripe, juicy, creative opportunity to be able to shape it aesthetically. And from an editorial point of view, when the opportunity of Pinterest came along, I had been thinking a lot about the way in which content creators and at Pinterest, when we talk about creators, we're talking about everyone from a creator can be Harper's Bazaar. It can be New York magazine or the cut. And it can be an individual who is like publishing great ideas.

So all of those types of creators are valid in our space. And I really am like powerfully moved by the fact that we get to create a world where so many people have a voice and that in many ways the playing field has been leveled for creators of all kinds. Whether you're like a teenager in a small town who's never going to work at a magazine or someone who is working at a publishing platform to be able to kind of shape a point of view.

And, you know, for for our kind of people who are passionate about storytelling, Pinterest is a great, you know, very exciting moment where we are developing our creators platform, creating new tools for for creators to use to to tell their own story. And Pinterest is really different from social media in general because it's about time for yourself. You know, it's where you go to find inspiration to style your next outfit to create a renovation in your home and envision where to travel.

And that aspect of a place where you go to find ideas to then bring into your real life is what excites me about Pinterest, because I think that we have all experienced I mean, certainly in 2020 where we've gone down a rabbit hole, is that like we've all experienced this world in which we just get lost in the Internet and it doesn't feel good. In fact, the science shows that people don't feel good when they're constantly being envious of other people's lives.

Whereas what makes Pinterest different is it's a place where you go to gather ideas, get get inspiration to then apply to your own life. So it's less of like a famo place.

Right. And it sounds like. It has creativity built in, it's asking you to participate and not to just sit there and let the feed wash over you, which so many it's such an experience of the Internet right now. Absolutely.

And I think it's like what is so crazy is that, like our interaction with the Internet has gone from that these apps and tools are like a place for us to gather information, to apply to our own life, to us being controlled by this thing and by controlled by I mean like spending our entire lives, like consuming other people's existences and focusing less on our own. And that is what is really exciting to me about a space like Pinterest, is that it is like a really creative platform where people come with a question to answer or a problem to solve, and we're able to provide that and then go off and live your life.

Having learned those things, are you a big Pinterest user?

Yes, I've been using Pinterest on my goodness for like since like, my God, my Pinterest account goes back to 2012. So I have been a user for a long time. And what is really exciting about our new tools for creators, which are one of them, is called story pins, is that it's a way to tell a story in a completely different way and to communicate ideas in a different way. Right now it's like an invite only tool.

But in in the new year, we will, like, launch it more widely. And it's been really interesting now that I'm inside this organization to see how our first unboarded creators, how they are using the tools, because everything that you would predict, all the modeling that we would have done to see how Pinterest users will become creators on our platform, it's like your mind just gets blown by what they actually do and the creativity that they express.

That's so cool. You've been at Marie Claire for about a year. Did you have a sense in the back of your mind of like at some point I'm going to go into the tech world?

Or were you like, you know, did you see this coming at all?

Were you expecting to make this career change at some point in your life? Or is it was it totally a surprise?

This was a surprise in the sense that I had no strategy. I had no strategy to leave my job because I love Marie Claire and I love all the brands that I have worked on leading up to that. So to me, I did not anticipate that this would become my path. But when I started learning about the Pinterest platform, which currently as of today has four hundred and sixteen monthly active users, you know, reaching 70 percent of U.S. millennial women, I was like, if I am able to shape the experience of these users and give them more exciting tools and educate them on how to use this platform better, then isn't this like the coolest magazine ever?

Isn't this the coolest publishing platform ever? Because as a magazine editor, what you do is your your shaping your own ideas and pushing them out into the world. But what my role is now here at Pinterest is to create the tools and educate the creators on how to publish their ideas. And that, to me, is like a way more impactful influence that I can have on, you know, the publishing space and creators around the world, then thinking that my own ideas are the coolest and the best.

Like, I don't I I want to make sure that I am here to empower others to tell their story. And that's how content lives now, because people want to be able to express themselves. And these platforms are now like creating some of the most exciting tools to do that. So so in in my feeling, when I got really excited about the Pinterest opportunity, it was because I was like, you know, I want to use this stage of my career to start empowering others to be creative in whatever ways they see fit.

And, you know, Pinterest as a platform is is one of the bigger, biggest consumer technology platforms ever created with over five billion boards and over two hundred and forty billion saved pins. Like it's it's a gigantic platform of ideas. And that to be able to make a contribution to that feels. Like an exciting next step for my career.

That makes sense to go really big picture for a second when we're were young and envisioning what your life is going to look like as an adult.

Was this what you pictured?

I when I was in fourth grade, I need to go to my parents house to find this thing. But we had to write a story about what our future was and I can still picture the cover. But of what I the story that I wrote, it was called I the Nurse from Mars. So that's what I pictured would be my life being an emergency medical professional on Mars. OK, so I haven't gotten there. So there's still time. You know, the life is long and I could still do that.

I haven't done that yet. That said, I am married to someone that works in the aerospace industry, so maybe he will get us to Mars and then we can build some hospitals. They're great.

Let's check back in in about 20 years and we'll see how the Martian winds going.

Special thanks to our guest, Iaconelli In Her Shoes is edited and produced by Brandon McFarland, our lead producer is Bob Parker, Stella Bagby and he shot her. Why are the show's executive producers? The cut is made possible by the team at New York magazine.

Subscribe today to support their work at the cut dotcom backslash. Subscribe. I'm Izzy Grandstand. Thanks for listening.