Photo via The Daily Front Row
I think that ambition is not a shameful thing, and so we should admit it, embrace it, analyze it. Figure out how to implement it.
Woman of Substance

Stella Bugbee

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For everyone who’s worried that changing careers more than once is a bad move, meet Stella Bugbee. She’s been a teacher and graphic designer; was the creative director at Domino when it was Domino; and went digital — and became an editor in chief — when New York Magazine asked her to run their fashion site, The Cut. She has since added president to that title, as well she should: Stella has created the smartest women’s magazine around.

The sections on The Cut include style, self, culture, and power. They describe this moment, true, but they describe Stella perfectly, too.

We talked about drive, accidental career planning, empathy through illness, and why she gets up so early to cook for her family of five. Please listen to the podcast so you can hear just how funny and unapologetic she is. Or is it unapologetically funny? She does not cut me any slack, and for that I am #grateful.

X: You had such a non-linear path to where you are, and I think that echoes what’s going on today. What gave you the confidence to toggle, and, in moments when you said that you felt like your career was completely over, what gave you the confidence to get through that? Stella Bugbee: It’s funny. When you look back, it looks like it was intentional. And I think I’m old enough now to admit that that is not the case, and that I had no idea whether I would recover from various obstacles in my path — including in my early twenties, when I was diagnosed with Crohn’s disease and feared that I might have to apply for disability and not work at all.   What did having an illness at such a young age teach you? It taught me that the assumptions that you have about different phases of your life are irrelevant. And that you can’t control things. And that even though your peers are doing one thing, it’s okay for you to have to do something different. It hurts, it sucks, it’s painful, it’s not necessarily what you would choose, but it’s also very valuable. Being sick at a young age — and I’ve only recently started to talk about it — was so incredibly humbling, and forced my hand in decisions that I wouldn’t have had to make. Like having children; when to have them. It seems like it was premeditated, but it was all accidents. The whole time.   Someone once told me that there’s never a right time to have kids. You can’t plan it. You’re too young, you’re too old, you can’t wait… I think I would’ve waited, for sure, if I was perfectly healthy. Also, being sick was very humanizing and taught me a bit about empathy and realizing that you really don’t know what’s going on in other people’s lives.   You taught at Parsons, you worked in graphic design — I love that you worked for the company that designed the posters for Rent and things like that. You went into peak Condé and got to help launch a magazine with a budget. And then you went digital. How did you feel when you would enter a new career, and how did people receive you? Not always well. Again, though, a lot of those decisions were out of necessity. I taught at Parsons so that I could get health insurance. I participated in the unionization of the adjunct faculty so that I could get health insurance. I loved teaching, it was really fun. It was not my primary source of income. I had used it as a supplemental source of income, because I started my own company, largely because I had Crohn’s disease, so that I could control my calendar. So these are choices that certainly they were talked about in my twenties, but I think are valuable to discuss now. And then digital was a decision I made because I could tell that after watching a magazine fail, that probably wasn’t a growth industry. I just decided to take a pay cut and a lifestyle change — and I don’t mean just like a lifestyle change, like a whole new medium. I was going to have to start from zero in and kind of just claw my way up again, and that was fine. I think that I get bored very easily, once I feel like I’ve mastered a skill. I was very bored by design by that point, and I wanted a change. And, honestly, no one ever gives you that chance. So the fact that somebody was willing to try me out in this medium with no experience…I think at those pivotal moments in your life, you’re like, I want to make a change, and somebody’s willing to help me make a change, I’m gonna do every single thing I possibly can to take the opportunity.   And now you have 27 employees? The Cut has 27 full-time people and a constellation of freelancers.   Amazing. So your job straddles two legacy industries, fashion and media. We talk about the disruption of things, but now I’m seeing destruction, seeing the end points. How has it been to observe from your vantage point? It’s been a very cool time to be working in fashion and in feminism and in digital media. Again, it seems intentional, but it’s all just luck. It’s like I came to the Cut when New York magazine had decided they wanted to make it more feminist. Who knew what was about to happen, culturally? It just… sometimes I pinch myself, like, I can’t believe I get to be doing this during this moment. It was the same way I felt when worked at Domino during the housing boom. I have no deep investment in the social and political structures behind fashion and the way it works, so I’m not upset by the changes. I find them worth examining and questioning, and it’s interesting to be observing and recording an industry in the middle of its free-fall to see, where is it gonna go? If I were deeply, deeply invested in it personally, that would be super alarming, but I’m not, so I’m able to have some distance.   What is it about your work ethic and your work and cultural metabolism that allow you to keep up with this? A few years ago you showed me your Slack feed and it started at 6 a.m. and ended at midnight — also factoring in that you have three kids and a husband. How do you stay on top of everything, and ahead of it? I don’t. I actually think I’m always behind. And it’s really just more that I’ve become comfortable being behind. I feel enervated by it. I like the people I work with, I love the content that we talk about, I love the jokes we make. I like fighting for them and what they stand for, and I don’t mind it. I think if you were the kind of person who values self-care over, like, your output… [laughs] I, personally, find it very, very satisfying to look at my work and feel proud of my work. The older I get, the more I’ve done, the less virtue I see in any choices. I just think it’s about doing what you’re moved to do, and if that’s chill, fine. I realize that what makes me happy is to be working super, super hard. That’s just who I am. I stave off my existential dread by working too much. But it works for me, and that’s fine. I wouldn’t wish it on anyone else. I had a conversation with my daughter the other day. I was like, “Don’t you want to be good at something?” — because she’s a teenager and her main passion is watching Gossip Girl. “Don’t you want to explore one of your many talents that you have?” She’s really great at so many things. And she said, “You know, not everyone’s like you.” Yeah. She was like, “I’m happy.”   How did you feel? I was really tense. I was like, wow. I got owned by my teenager so hard. It was a good moment for me to hear.   You’ve talked about the importance of having a network, and that you couldn’t have gotten where you are without one. Tell me about how yours has impacted you. I think there’s a strong reality to, you don’t succeed unless other people want you to, and that you must have the support of the people around you. Very few people are entirely self-made.   You told the Coveteur that ambitious women are the core of the Cut. Do you think that women still feel they have to disguise their ambition, sit on their hands a little bit? I mean, I’ve never disguised my ambition, so it’s hard for me to say. But it’s more, actually, that I feel like people find ambition off-putting, even other women. I think that ambition is not a shameful thing, and so we should admit it, embrace it, analyze it. Figure out how to implement it. Unchecked, it’s not useful. But, like anything else about your personality, if you kind of figure out how it fits into your life and how you want to use it, then I think it can be really, really powerful.   The how-does-she-do-it rubric has become incredibly popular. It’s funny, because right after I wrote this question, the Cut newsletter came through with the “How does she do it?” It’s “How I Get It Done.” Do you want to re-ask that question?   [Laughs] It’s a question I have of all of my friends, because it’s something that we all crave answers to. I think none of us, no matter how successful we might seem on the outside, feel like we’re doing quote-unquote “it” at all, at least not as well as we’d like to. So do you think anyone has really nailed the work-family-love #selfcare balance? No. I’ll just use my own example. I like to get up really early and cook and be with the kids and do a load of laundry. And the thing I’ve sacrificed is exercise. I never do it, ever.   I have been happy to see in the last year or so this movement toward being messy on Instagram and not like, yay, I’m so cute, and I just woke up like this, and now I’m meditating, and I’m grateful, and I’m blessed. I get up and I meditate and I make food and I hang out. I’m not a mess. And I’m not gonna pretend to be a mess. I have my shit together. I think it’s just, like, don’t pretend to be something, period. If you’re a mess, be a mess. If you’re not a mess, don’t pretend to be a mess. And don’t apologize for that, either. When I did that… when Bon Appétit interviewed me about my morning, I got so many people being like, fuck you.   Because you get up and make three dishes? I was like, you know what? I never said you should. That’s what I like to do. That’s what gives me a sense of control over my life and my day. Not just a sense of control, but a sense of humanity and being grounded, because I really like to cook, I love food, I love to eat a meal with my kids at the end of the day, and I don’t like to necessarily rush home and do that. These are just choices. It’s not… I’m not saying I’m a better person, or you’re a bad person because you don’t do it.   Do you consider cooking a creative outlet? I think it is easy to feel divorced from the small things that make your day human, and whatever it is about standing in front of the sink and washing vegetables and chopping them makes me feel like I’m doing something that I want to do and that’s going to be good for me and it’s not about advancing any agenda.   Do you think in this day, with the email and the schedules and the Slacking and the cooking and everything, do you think it’s still possible to have a rich inner life? Um, absolutely.   When? How? My father always used to talk about, you need to have one moment every day. And the moment would be anything from looking across a room and enjoying the way the sun was coming through the window and that was your moment. Or seeing someone on the street, running into them and hugging them, because you hadn’t seen them in a long time. Or you’re just sitting down to have a really delicious drink at the end of the day. Whatever it is. A single moment — if you could have a single moment every day — that would be ideal. And not to prescribe what that would be, but just make sure to recognize that they were happening. I don’t know if I just internalized that, but I definitely have one at least every day. And it could be biking over the bridge or just I see things on the street that make me laugh. And I don’t think it’s like social media’s necessarily not part of that. Sometimes I’ll see a friend of mine post a picture of her child and it sparks an idea or I feel joy and happiness about them and to me that’s an inner life, too. I don’t think it’s like one or the other.   There’s this funny chart that Paula Scher did about one’s twenties, thirties, forties, and fifties, and fifties is absolute power. And then it becomes emeritus status. What are you excited about in your forties and fifties? Do you see a consolidation of power coming in your life? No. I fully expect to be working for the people that are working for me now. I don’t think power is linear. I don’t think people have any kind of guaranteed success in life. I think tides change and people’s sensibilities come in and out, and that there will be another sensibility that will replace this one. I’m grateful to have been able to do anything, honestly. I think that pretty soon the millennials will have all the power. It’s funny, I say this to several people who work for me all the time: Just give it ten years––you guys are gonna have all the power, I promise you. It seems like you never will, but there will come a day where every person you know will be in a position of power. I just hope there will be work for me. I don’t mean that in a dark way. I know this sounds corny, but in a very humble way, I just hope that I get to make any money and have health insurance and do what I like doing. I so never expected to be able to do that, and I still feel lucky every day to get to do that. And, God, wouldn’t that be amazing to get to do that for another two decades? It would be very, very unexpected for me. But who knows? You just don’t know.