If you are remotely into fashion and have watched The Devil Wears Prada (or rewatched ad nauseum, we don’t judge!), you’ve probably wondered what it’s like to be Anna Wintour’s assistant—even if just for a day. Thankfully, you don’t have to wonder anymore because some of her former assistants are pulling back the curtain on what it’s like to work for her, and they're giving fashion aspirants invaluable advice if you want to start your career in the industry.
In honor of the release of The Devil Wears Prada 2, Wintour’s former assistants Sammi Tapper and Marley Marius, now, respectively, director of operations and content strategy, and senior editor, features and news at American Vogue, sat down with Teen Vogue to reminisce about their beginnings as assistants and share the best pieces of advice from the lessons they learned.
As told to Alyssa Hardy and P. Claire Dodson, find Tapper and Marius’s best advice here for getting started in your career, whether in fashion or elsewhere, from learning to move on after making a mistake to not being afraid to ask for help, and more. And if you want more, listen to their episode of The Run-Through with Vogue to know what The Devil Wears Prada got wrong and what it got right.
On picking up after a mistake:
Sammi Tapper: As much as you can, try to separate yourself from the moment when you make a mistake. When you’re starting out in your career, you will likely make a handful of trivial mistakes. Sometimes, you can be made to feel like they are the end of the world. It’s important to take mistakes seriously and learn from them, but also to ask yourself, “Is this going to matter in a week? Is it going to matter in two months?” - if the answer is no, I try to move on as quickly as I can. I don't remember any of these mistakes in my first year in Anna's office right now, but I know at the time, I would think, “Oh my god, I feel so distraught over this thing.” At the moment it can feel like the end of the world, but remember no one is perfect, and it’s all part of the process.
On finding your peers at work:
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Marley Marius: Who you're working with in the office makes a big difference. When I was in Anna’s office, there were three assistants, and we all got along well. Even though we had different responsibilities and weren't all super close, we were friends, we found each other amusing, we were on the same page, and communicated well. That was huge because I found that in that office, it could be a bit isolating. You know everyone, you know what everyone does, but you're mostly just interacting with your fellow assistants and with Anna, so it’s helpful when you feel like you can trust the people immediately around you. That would certainly be the case in any workplace: If you like your team, that makes a huge difference in how your day goes, the quality of your life, and the job.
On getting into the entertainment industry:
ST: My first job was at CAA. I recommend that if anyone's interested in media talent, talent agencies are a really great place to start your career. There's a one-to-one, agent-to-assistant ratio, and half the company is people under the age of 28. Everyone worked hard, but it was also really fun.
On embracing scary challenges:
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MM: I do feel I'm constantly presented with things where I'm like, I cannot do this. And honestly, that's a post-Anna's office thing. There have been lots of writing assignments that brought me to my knees, but you have the experience, you survive it, and then you're like, Okay, that didn't actually kill me. I got through it, and I got reasonably positive feedback.
I've been dropped into situations that I would never put myself into, but ultimately they were positive and productive, and it's sort of edifying. Being at Vogue has meant being in scary meetings, doing interviews with intimidating people, or having to cover an event where you have to walk up and talk to people, which is mortifying to so many parts of my personality. But you do it, and then you realize you can do it, and eventually it becomes a skill set. It's been nice to realize that things I didn't think I could do are possible.
ST: There's a lot of power in overcoming anything. The first time you do anything, you don't know if you can do it until you do it. I remember that's how I felt with everything in Anna's office. The second year, when you become the first assistant, each task or challenge just feels better because you're like, I've done this before. I've been through this. Something can feel so daunting, then once you do it, you're like, Oh, it wasn’t as bad as I thought it was going to be. With anything, just remember the fact that this is new, it's going to be scary, but also that you're young, and it's supposed to feel scary. You're not supposed to have all the answers when you start. I think it's just having that patience and being really kind and gentle with yourself when you're going through something new.
On not being afraid to ask questions:
ST: It's important to figure out what you don't know and be honest about that with yourself. And also understand why you might be procrastinating or not doing something. Procrastination was often an issue for me when I first started. I would realize that, Oh, I'm not doing this because I'm scared that I don't know how to do it. And then I started to shift my thinking to, How can I figure this out and do it? You don't know a lot when you're younger, and that's okay. But know what you don't know. Say what you don't know and ask the questions. Never take a guess or pretend to do something early on in your career. Just ask the questions. Ask smart questions. It's okay to ask and then learn quickly.
MM: I definitely had experiences where I tried to do something on my own because I was too embarrassed to ask the question, and that was a big mistake. I quickly learned that you just need to risk embarrassing yourself to avoid embarrassing yourself even more. But there were also definitely moments in Anna's office where something would go wrong, and I'd be like, Marley, you are 22 years old. She knows that you're 22 years old. This is a learning experience. And she’s had so many assistants. You’re not going to have many experiences that another person has not had in this office.
It's all going to be a big learning curve. And a lot of the time, people are happy to help. They're happy to answer a question because I think they also realize that it’s going to save everyone work later on if you learn how to do something correctly the first time.
On nurturing your passion and being persistent:
MM: I talk to a lot of college students and people who are trying to become writers or work in fashion media. What I tell them is that it’s nice when you have a byline at a fancy place. It's a nice thing to have on your résumé. But if you want to write, write however you can for whomever you can, make a Substack, submit to a small magazine. The important thing is to hone that skill. It doesn't have to be at a big company; you can work on it on your own. Persistence pays off. A lot of it is luck, too. I feel that I was very lucky and very privileged to end up where I did, but I also had a very clear idea of what I wanted. [Knowing] the right people certainly helps, but persistence will get you somewhere for sure. It sucks, and it's boring, but there's no substitute for the work and building up your skill set.
On not comparing yourself to others:
ST: Everyone's on their own timeline. A metaphor I often think about is planting seeds. Plant as many seeds as you possibly can because one is sure to sprout. Sometimes those seeds are LinkedIn messages and meeting people for coffee. There were people I would reach out to on LinkedIn when I was a sophomore in college, and I'd ask for a 15-minute Zoom. Then, when I moved to New York, we would meet in person for coffee, and now they've become my colleagues. Things eventually come full circle, even though there might have been seven years in between. Plant those seeds. An action you take today might not see results in one, two, or three years, but have patience. You never know when that action will pay off.
This interview has been edited and condensed for clarity.
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