Introduction
In 2020, the New York Times published an article titled “Can Anna Wintour Survive the Social Justice Movement?” The article lambasts Anna Wintour, EIC of Vogue Magazine, for being the queen of elitism. She hires thin white Ivy League women as her assistants, she promotes thin white models, and she told Oprah Winfrey to lose 20 pounds before she could grace the cover of Vogue magazine—which Oprah duly did. Would Anna get permanently canceled in 2020? It seems not. Four years later, Anna still runs Vogue, and young women in fact seem to look up to Anna’s sort of hyper-exclusive, queen bee energy, more so than they seem to want to cancel her.
If you want to learn how to gain power through exclusivity, there is no one better to study than Anna Wintour. Anna is the queen bee of queen bees. Since she was young, she’s been able to make every woman around her want to be her, and every man around her want to be with her, and she’s channeled that ability into creating a very successful career.
In addition to running Vogue magazine, she is chief content director of Conde Nast, the parent company that owns Vogue and 32 other magazines, including The New Yorker and GQ. The film The Devil Wears Prada was written about her, by one of her former employees. She organizes the annual Met Gala, she’s extremely involved in Democratic Party fundraising, she’s a fashion icon, she’s nicknamed “Nuclear Wintour,” she’s been the subject of numerous documentaries.
In this episode, I will break down for you what’s made her uniquely successful, and which of her tactics you can learn from even if you don’t naturally have a nuclear winter kind of personality.
Childhood
So let’s start at the beginning. Anna was born in 1949 in London, to a seemingly happy family. Her parents were wealthy and in love, her dad was on his way to becoming a hotshot newspaper editor, and Anna was their third child. Everything seemed great. Until... one day when Anna was one year old. Anna’s oldest brother, Gerald, was 8 at the time, and went on his daily bike ride to school. On his way there, a car ran over him. He died almost instantly.
Anna’s father, Charles, was working his way up as a journalist at a prominent newspaper at the time. Gerald, as the eldest son, had been his favorite child, his pride and joy. At the time of the accident, Charles was in a meeting with Lord Beaverbrook, the media mogul who owned his newspaper. A butler pulled him aside during the meeting to inform him that his son had died. Charles simply nodded and continued with the meeting as though nothing had happened, only rushing to the hospital after the meeting had concluded. This episode reinforced his nickname “Chilly Charlie” because of his coldness. It really impressed the big boss, and from then on Charles rapidly rose through the ranks of the newspaper.
As advantageous as this was for Charles’s career, the episode ruined their home life. Anna’s mother, Nonie, fell into depression and paranoia, dedicated herself to social work, and lost respect for Charles. Family friends described a chill that ran through the entire household.
Anna inherited a lot of this; a family friend recalls that “even as a child she had her father’s coldness.” When adult guests came to the house, she didn’t hesitate to set the agenda or ask them to do things for her. At family reunions, her relatives were shocked at her rudeness: if she didn’t feel like talking to anyone, she’d simply ignore them, even if they were a cousin or aunt. If anyone was ever late to meet her, she would simply cut them off.
She wasn’t just cold toward others, though—she was most rigid of all toward herself. She was extremely self-controlled, and a big part of that manifested in being obsessive about her looks. As an adolescent, she ate little more than a single apple in the entire school day. Today, at the age of 74, she still rises at 5am every morning, exercises for 30 minutes, sits for 30 minutes to get her hair and makeup done, and hasn’t been known to gain any weight since the age of 18.
At school, Anna had virtually no friends besides one girl named Vivienne, who was her best friend. Was she shy though? According to Vivienne, no: “She didn’t want to be part of a group that existed. She wanted to be in her own rarified air. She wouldn’t go out of her way to sort of connect with this one and that one unless it [was] truly necessary.”
And even though Vivienne was her only friend, Anna was definitely the queen bee of their two-person clique. They were both obsessed with being thin, but Anna was thinner than Vivienne, and she would rub it in Vivienne’s face. Anna learned to cook Vivienne’s favorite food, lamb chops, just the way Vivienne liked them—and she would invite Vivienne over to have these perfectly homemade lamb chops, with her favorite cheesecake, and she’d just watch her eat, and not have a single bite herself. For Vivienne’s birthdays, she would buy Vivienne these gorgeous expensive dresses as gifts, but she would buy them in her own size, which was one size too small for Vivienne, and Vivienne would just not fit into them. There’s no way Anna would’ve known all the details of Vivienne’s favorite foods, but not known her actual clothing size — this was definitely on purpose.
I think the shallow interpretation here is, omg, Anna is so catty and just needs to assert her dominance always. Which is fair. But I think there’s also an element of like - people who are extremely self-controlled often feel a sense of both disgust and fascination at the sight of perceived weakness in others. When I think of teenage Anna, so committed to being thin, watching a comparatively chubby Vivienne wolf down lamb chops; I can imagine she must’ve felt such revulsion, perverse desire, and self-hatred.
Ok, and this all happened during the Swinging Sixties in London. It was a time of youth, optimism, hedonism, creativity… anything cool and new that happened culturally, took place in London. Think the Beatles, the Rolling Stones, women wearing short skirts for the first time. Anna was obsessed. When she was 15, her parents let her move into a standalone apartment on the ground floor of their house, with its own separate entrance. She decorated it all herself in the latest style and started living this unusually independent life at 15.
Every Friday night, she and Vivienne changed into their evening looks (usually miniskirts), and at exactly 11 p.m., they would hail a cab to one of London’s hottest nightclubs. The point was not to go partying; they went to survey the fashionable crowd and see the latest trends.
Anna loved the excitement of being at the cutting edge of culture, which was probably also influenced by her father—at dinner every night, their father’s excitement about the latest news was always infectious, and she later recalled that it was incredibly exciting to be hearing the latest news and gossip from him before it hit the front pages of the newsstands the next morning.
On Saturday mornings, Anna rose early to line up outside her favorite clothing store, Biba, which churned out all the latest fashions at a cheap price. She also had her hair cut into her signature bob style that she still wears to this day, and would get her bangs freshly trimmed every week.
However, her obsession with fashion got her in trouble at school. She went to a very posh all-girls private school that was run by Victorian-era headmistresses, and students were required to wear these stiff, shapeless brown uniforms that Anna loathed. So she was always trying to hitch her skirt up to look a little shorter, and skipping school to go shopping. One day, she finally hitched her skirt up a little too far, and got expelled. So to this day, Anna Wintour does not have a high school diploma, thanks to her miniskirt obsession.
She also started dating older men around this time, which is a pattern that would hold throughout her life. Her first boyfriend was 24 when she was 15. It seems kind of clear that she was looking for a bit of a father figure: someone older, intellectual, often a writer or artist, often emotionally unstable. She idolized her father her entire life, cared always about his approval, but was hurt and confused by his many extramarital affairs and his relentless prioritization of work over family — and all this seemed to come out in flirting constantly with older men.
This ended up being great for her career on two levels. First, it gave her great practice in dealing with talented men with big egos, and these guys would help her meet important people and advocate for her in getting cool jobs. In fact, if you fast forward in her career, almost every career opportunity she got was from a boyfriend, an ex boyfriend, or her father.
How did she do it? My guess is that underneath her nuclear wintour persona lies a soft person who had a damaged childhood. With her boyfriends, she played the lost little girl—leaning on them, relying on them for advice, evoking their protective, almost-paternal feelings toward her. A former colleague recalls that she would just stand there, her hair almost covering her eyes, so slender and waif-like, with her miniskirts and sheer blouses that were both chic and sexy at the same time, and the men would just line up to carry her suitcases for her—almost like a Lolita sort of charm. It reminds me of these lyrics from the song Cigarette Daydreams:
Cigarette daydreams
You were only seventeen
So sweet with a mean streak
Nearly brought me to my knees
I think something about this slender little girl, who was at once so fierce and determined and smart, yet also clingy and sweet and looked up at you with her doe eyes, got men really crazy over her.
On a deeper level though, I think that fashion is ultimately about power, and I think there’s a sort of symmetry and resonance between her keen eye for fashion trends—what’s in and what’s out—and her keen eye for how to seduce and gain power over both men and and women. You see that as a teen, Anna is repeatedly dating men who are a decade older, which today would be literally illegal on the part of these men, because our legal system assumes that the men are taking advantage of the teen girl—but there’s no evidence of that in Anna’s relationships. On the contrary, Anna uses her sex appeal and keen understanding of psychology and power dynamics to stay in control of her much older partners.
For example, her very first serious boyfriend, Jon Bradshaw, eleven years older than her — she cheated on him multiple times, she started her next relationship before breaking up with him, he was frequently out of mind with jealousy and Anna would literally have her assistants lie to him about her whereabouts when he called her work phone. Decades after they break up, he’s literally married to another woman, and she’s still calling him all the time, asking for career advice and such. Bradshaw’s wife is like, stop talking to Anna, I hate this woman, it’s so clear she’s manipulating you—even when she’s editor of Vogue she’s still calling him, playing the part of the lost little girl, relying on his advice—but Bradshaw ignores his own wife and still lets himself continue to be charmed by Anna. He picks up the phone whenever Anna calls, literally until the day he dies.
How does this relate to fashion? Well, let’s contrast this story with that of Anna’s mother, Nonie. Nonie comes from a super rich family, she’s super smart, she meets Charles Wintour at Cambridge, and he falls in love with her mind and character. But all that is not enough to keep him. Charles has repeated affairs with younger, more fashionable women. Nonie is too proud to wear nice clothes or play mind games to try to keep him around. Eventually Charles leaves her to remarry a young, fashionable woman, and she and the kids are all devastated. I’m sure this must’ve taught Anna at a young age that, for women, unlike for men, all the intelligence and all the money in the world does not translate to ultimate power; sex appeal and fashion is a woman’s currency.
Early Career
Anyway, after leaving high school, she worked an entry-level job at a department store. Then she heard about a fashion assistant role at the fashion magazine Harper’s Bazaar. Thanks to a combination of her own abilities, her dad’s friendship with the editor, and her boyfriend’s job as a fashion photographer, Anna got the job. She was super ambitious and hit the ground running. A colleague recalled: “There were other girls who were more talented... but didn't have that incredible drive that Anna had... Anna had this total conviction that she was aiming for the top job. She had very precise ideas about clothes, a very good sense of quality, but nothing adventurous, always rather conventional... very much in the mainstream.”
Ok two things are interesting here. First, her ambition; from age 17 she’s aiming for “the top job,” even without a high school degree. In fact, it’s during this time as a fashion assistant that she first announces to everyone that she would like to one day be editor-in-chief of Vogue. This ambition seemed to stem from her father: Anna says that one day, she had to fill out some form or other that asked what she planned to do with her career. Her father said, “well, of course, you say you want to edit Vogue,” and so it was decided.
The second interesting thing here is, you might think she’s like this creative visionary fashionista, but no. Her tastes are very mainstream, one might even call her basic, and that is the whole point; that is what makes her great. She is the ultimate basic girl; she knows exactly what is most mainstream, or more importantly, what is on the cusp of exploding into the mainstream. That’s her talent, and it’s extremely valuable in fashion journalism.
As a teammate, she was both terrible to work with and really good at getting her way. She was sharp-tongued and critical of basically everything about everyone, especially their clothes. And she was kind of just a bully — like what she did with Vivienne, but times ten.
At the same time, she was extremely good with working with photographers, which people usually viewed as the most challenging part of a fashion assistant’s job. Her editor would come up with a vision for the photoshoot, and Anna’s job would be to get the photographer to execute on that specific vision. But, you know, these photographers are creatives, they're artists with their own strong vision for what they want to produce. They also tend to be overwhelmingly male and have big egos. So a lot of young female fashion assistants would just get bullied by these photographers. But not Anna. Remember, Anna’s been dating these kinds of men since she was 15, and manipulating them has always been one of her strengths. As a colleague observed, “Anna flirted, ego-stroked, and slyly directed in order to get the best out of the photographers.”
A few years in, Anna’s boss, the fashion editor, got fired. So Anna started gunning for the fashion editor role, even though she was age 24 and not a good writer. First she got her bf to take the top editors to lunch and make a case for her - that failed. Then she got her dad to make a case for her - that failed too. So Anna quit her job and moved to NYC at age 25.
She got an assistant role at the American Harpers Bazaar in New York, where she clashed strongly with her higher-ups. She was extremely determined to exert her own taste, even as a junior staffer, which infuriated higher ups. She clashed constantly with the EIC in particular, who was also a super controlling person. Nine months into the job, Anna was fired.
She spent a couple months job-searching with increasing desperation, when her ex-boyfriend got her an interview with a magazine called Viva. It had a reputation as being a sort of porn magazine, but they offered Anna the role of fashion editor, where she would have almost complete creative control over the fashion section of the magazine. Anna took the role. This is where we first see what Anna is like in a leadership position.
Leadership Style
So what is Anna’s leadership style? First, she had a clear vision, and she executed on it in an extremely efficient, decisive, and determined way.
When a model tried on clothes, most editors would ask to see different angles, think for a bit, maybe call in a second opinion. Anna would just go yes- no- yes- no- with no hesitation. She hated long meetings. With Anna, people say, “You get two minutes, the second is a courtesy.”
And she started hiring assistants. She was notoriously demanding toward them. Former assistants recall Anna pounding her fists on her desk in rage because she couldn’t read an assistant’s handwriting on a note, and getting testy if they were late to bring her coffee. She’d also blame the assistants for anything that went wrong, even if it wasn’t their fault. One time, Anna’s boss got mad at her for spending too much money on a photoshoot, so she simply blamed it on her assistant and fired the assistant.
But people still kept lining up to work for her. One of her assistants, Georgia Gunn, served her for years at three different magazines. Anna attracted employees who admired her talent, and who understood that she was brutal because she wanted to get a lot done and simply couldn’t stand inefficiency, laziness, or weakness of character. I think this about knowing what you want and who you are—if you are unabashedly yourself, people will be attracted to that—even if who you are is kind of a bully.
And Anna produced good work. She started developing a signature style — glamorous, sweet, a bit sexually suggestive. Editors from Vogue started looking at Viva, just to see what Anna was doing.
Finally starting to make it
Four years into Anna’s tenure, Viva magazine shut down due to financial difficulties. Anna cried. She spent the next year and a half traveling around the world with her new boyfriend—the first real career break she had since leaving high school. Then, at age 31, she returned to New York, broke up with the guy, and took a job at a new magazine called Savvy that had just started.
Unfortunately, this job was doomed from the start: the magazine wanted to cater to professional women in fields like business and law; Anna wanted to shoot glamorous spreads aimed at fashionable It Girls, so that she could add to her portfolio and eventually get hired at a fashion magazine like Vogue. Anna’s boss tried to fire her—but somehow Anna managed to talk her boss into letting her stay a little longer, and started furiously job-hunting in the meantime.
Her latest boyfriend got her an interview at New York magazine, and she became their fashion editor—finally her real “legit” fashion editor job, at age 32. When she walked in on day one, she tossed out the desk that she was assigned, and replaced it with her own beautiful white desk. Her new colleagues looked at each other and were all like, oh boy, here comes the diva. But there was one key difference between this and her previous roles: her boss, the editor in chief, was a huge fan of Anna. A colleague recalled: “He thought the world of her. He also adored her because she was beautiful and charming. I think he had a little crush on her.”
So it was a great gig, but Anna still had her eye on the grand prize—Vogue. And Vogue started looking at her too. She got called in for an interview with the Vogue Editor-in-Chief Grace Mirabella, but at the end of the interview, Grace asked what role she most wanted at Vogue, and Anna said: “I want your job.” So Grace did not hire her, and in fact hated her from then on. But Grace wasn’t the biggest boss. Vogue is owned by the media company Conde Nast, and Grace had to report to her boss at Conde Nast, Alex Liberman. And Anna of course developed an amazing rapport with Liberman.
So Liberman, against Grace’s wishes, offered Anna the role of creative director of Vogue, and she took it. After getting fired from two jobs, Anna finally seemed to have internalized that it is really important to maintain a good relationship with the people who have power over you.
And she became a master at it. She would spot who had the real power (aka Liberman and the guys at Conde Nast) and who didn’t (aka Vogue editor Grace Mirabella). Luckily for her, the people with real power were men, and she would just absolutely charm them.
So Liberman, the Conde Nast boss, used to be Grace Mirabella’s mentor - Grace used to be his favorite, his trusted one. But Anna was really careful to cultivate her relationship with Liberman - she’d run her editorial decisions by him, pitch him creative ideas, etc. And she started to replace Grace in his eyes. Soon Liberman promoted Anna to senior editor.
Anna started quietly making edits and decisions without consulting Grace — even though Grace was technically her boss, she started acting like she reported directly to Liberman.
Obviously, Grace felt really threatened by all this and started rallying the staff to be loyal to her instead of Anna. So the office got split between Grace loyalists and Anna followers.
But Anna didn’t get too caught up in fighting with Grace over who was on whose side—she stayed focused on producing good work and cultivating her relationships with the Conde Nast guys, and used the war with Grace to her advantage. One time, Liberman wanted her to work closely with this girl Blanche, who he thought was brilliant but who Anna hated. In a previous life, she might’ve just been like, no, I’m not working with Blanche—but this time she knew better than to get on the big boss’s bad side. So to get rid of Blanche, one night Anna invited Blanche to a party out of the blue. Blanche’s like, uh, wow, I thought Anna hated me, but ok, I’ll go. The next day, the two of them are meeting with Grace, and Anna just starts going on about what a great time they had at the party together - basically making it sound like she and Blanche were bffs now. So Grace is like, what? Blanche is on Anna’s side? I’ve gotta destroy her — so Grace got rid of Blanche, and Anna no longer had to deal with her.
So Anna keeps earning more trust with Conde Nast, and a few years into this, they make her the Editor-in-Chief of British Vogue. This is not the position she wanted—because this whole time she’s been angling to replace Grace as EIC of American Vogue, which is more prestigious than British Vogue—but nonetheless she takes the position and moves back to London.
Immediately after taking over British Vogue, she fires and replaces most of its staff, and gives the magazine a whole new look and feel. Obviously very controversial, but the important thing is that she left a great impression on her Conde Nast bosses, who think she’s set a brilliant fresh vision and infused the British magazine with a new work ethic.
The entire time though, Anna clearly still has her eye on editing American Vogue. A year into her job, Anna tells Conde Nast that she can’t stand London anymore, and her bosses were like, ok, we’ll get you back to the US. They put her in charge of their Home and Garden magazine in New York, where once again Anna terrorizes the staff and tries to turn it into a more upscale, glamorous magazine in the shape of her own tastes.
8 months in, she gets named Editor-in-Chief of American Vogue.
The way it happens is — A French fashion magazine called Elle had recently expanded to the US, and they were doing insanely well. The Conde Nast guys were extremely concerned and kept urging Grace to get Vogue to look more like Elle, and compete to grab their audience—but Grace wasn’t aggressive enough about it. Also, Grace had neglected to build a strong relationship with the other leaders of Conde Nast—she was close to Liberman and thought that was enough, but no, Liberman was only one of two head honchos at Conde Nast.
So one night, Grace’s husband turns on the TV and sees a gossip reporter say that Grace is about to get fired from Vogue. Grace calls Liberman. Liberman says, sorry Grace, I’m afraid the rumor’s true. We’re replacing you with Anna. And that was that.
How she grew her power
Ok, so how has Anna kept her position for so long, and avoided being unceremoniously fired the way Grace was? A couple things.
First and most obviously, she kept her bosses happy. So she kept up a good relationship with them, and kept business metrics and revenue top of mind. We know Anna is incredibly specific in her tastes and insistent on having her own way—but she quickly learned to prioritize advertisers’ interests over her own taste.
One big thing she did to grow revenue was to put a lot of celebrities on the covers of Vogue to boost sales. In the 80s, people saw Madonna as trashy and scandalous. A reader told Anna that he viewed elegant, sophisticated Vogue as the last magazine on earth that would ever associate itself with Madonna. So, the next month, Anna put Madonna on the cover. The cover photo is very toned-down, yet subtly sexy—it’s a simple headshot of Madonna in a swimming pool with wet hair, no jewelry, minimal makeup, no cleavage or anything. It was—and still is—an iconic cover that sold 200,000 more copies than the previous one. She also made a splash by making Hillary Clinton the cover girl right after the Monica Lewinsky news spilled.
Second, Anna maintained her pulse on what was hot and new. Even as she herself aged, she kept her staffers young—several former employees contemplated suing her for age discrimination. Also, when the Internet was invented, most journalists were extremely suspicious of this newfangled technology, and avoided it with an intense fear and paranoia. Anna embraced it—she made Vogue one of the first fashion magazines to go online.
Third and most importantly, Anna used her position at Vogue to build up her own personal brand, reputation, and connections. She became the leader of the fashion industry, and accumulated power more broadly in entertainment and politics too. By building up her personal power in this way, she made herself more than just another editor, and thus made it a lot harder to find a replacement for her. Let me explain.
First, she became extremely well-connected with all the players in the fashion industry, and became a person who facilitated business connections between other people in the industry. As editor of the biggest fashion magazine in the country, she naturally had a lot of clout already. She used that clout to make herself the leader of the fashion industry. She would host these dinners and events where she was extremely deliberate with the seating arrangements—she would think through every single seating placement at every single table, to maximize the chances that her guests would have interesting conversations and strike business deals. So that way, Anna became the person who facilitated deals, the person whose parties you wanted to be invited to.
She also established the CDFA / Vogue Fashion Fund, which singles out young fashion designers to receive funding, mentorship, and connections to the big fashion players in her network. That way, she consolidated control over which young designers would make it, and which wouldn’t. And once they became powerful, they would continue to ask Anna for advice.
She maintained control over them not only with her connections and money, but with her fearsome personal reputation.
For example, one designer recalls that Anna fell in love with his clothes and started featuring them in Vogue regularly for a few years. One day, her team came to survey his collection for a fashion show, and told him that there were two dresses in particular that they didn’t love. He was like, whatever, I’m just gonna show the dresses anyway. After this transgression, Anna and her team never spoke to him again. The next time he saw Anna, she looked at him for two minutes, said nothing, and then walked away.
With stories like that, young designers were constantly on edge, eager to please Anna, praying they wouldn’t accidentally do something to fall out of her favor.
Anna’s superpower has always been her ability to spot trends—but now, increasingly, she was able to personally influence the trends.
Simultaneously, she leveraged her network to start organizing huge charity events. The first one she ever did was called Seventh on Sale, to raise money for AIDS. She got a bunch of fashion designers to donate some clothes, and organized a huge clothing sale where people could buy them at a discount. On opening night, she put together a super fancy dinner that people paid $1000 each to attend. She raised almost $5M for AIDS. It was amazing publicity for both her and for Vogue—it associated both of them with a popular liberal cause.
She also started organizing the annual Met Gala for the Metropolitan Museum of Art. She made it into a huge exclusive thing, so much so that as of 2023, she’s able to charge people $50k per person to attend. So this increased her clout even more, and expanded her influence beyond fashion to include entertainment and celebrities. Harvey Weinstein became obsessed with getting Anna Wintour to his film screenings, believing that an endorsement from her would help him win more Oscars.
Then she expanded her influence to politics, too. When Obama was running for president, she organized a bunch of fundraisers and became a significant donor to his campaign. This gave her powerful political connections and even put her in the running for a US ambassadorship.
In addition to all this, her personal image has gone mainstream. In 2006, the movie The Devil Wears Prada came out, clearly referring to Anna as the devil, with her bob haircut, her upper-class British accent, her decisive ways, and her sunglasses that she never takes off, making her an object of fascination with a whole new generation of young women.
All this has translated to increased power at Vogue and Conde Nast. Remember, Anna’s predecessor was fired because she couldn’t deal with the rise of one new fashion magazine. Anna, on the other hand, has remained editor-in-chief through the rise of the Internet, the rise of social media, the rise of YouTube and Instagram and now TikTok. Not only has she held onto her position, but she’s also been promoted to chief content officer of all Conde Nast publications.
Let’s be real - Anna may be super-talented at keeping up with what’s new, but... the woman is 74 years old. Surely there must be at least a handful of other talented, young, fresh editors who could ostensibly do a better job of literally editing Vogue. But Anna has made herself seemingly irreplaceable, because she’s accumulated so much influence in so many spheres, and become a fashion icon in her own right, in a way that no merely talented person could compete with.
So: yes, you should suck up to your boss, but that is only step one. Yes, you should always keep business revenue in mind, but that’s only step two. To keep growing your power and longevity, you must keep boosting your personal brand and your company’s brand. You must make yourself the center of a growing web of ever more powerful, intelligent people. You must not only observe and predict trends, but also be able to influence them.
Personal Life
Ok, the final component to her success was being militant about delegating tasks and valuing her time very highly. During her time at Vogue, she actually had two kids — and two husbands.
Anna was quite involved in her kids’ lives, as much as she could be, and both her kids seem really well-adjusted—one’s a doctor, one’s a film producer, both are happily married, and her daughter even posts frequent Instagram photos with Anna that suggest they’re quite close.
A big part of how she managed all this was by being militant about delegating all busy work to her assistants and staff. She usually had 3 assistants at a time. The first assistant managed the other two and handled Anna’s schedule. The second assistant managed her private chef and house caretakers, and took care of her dogs. The third assistant ran errands, helped with fashion week, and ordered Anna’s clothes.
Every morning around 7:30, Anna would call them saying she was 15 min away from the office, and that would be their cue to fetch her Starbucks latte and blueberry muffin. Once her car pulled up, they met her at her car to carry her tote bag upstairs, and pulled out a notepad to furiously write down everything she said—because as soon as she arrived, she just started talking, issuing to-dos without periods or pauses.
At the end of every day, no matter how important of a party she was attending, she made sure to be in bed by 10pm, so that she would be fresh and energized for the next day.
Conclusion
To wrap it all up, here are four things we can all learn from Anna.
#1: Be yourself. Whatever your personal brand is, lean into it. Anna’s personal brand of being very cold and definitely worked for her in building a sense of mystique around her, but ultimately, people admire and are drawn to Anna despite her mean girl energy because she is so unabashedly herself.
#2: You do need to suck up to the people with power. This may or may not be your actual boss, but someone needs to advocate for you.
#3: Expand your personal brand and network, by becoming a host and superconnector of the powerful and intelligent—which is very different from indiscriminately attending any networking event you’re invited to.
#4: Treat your time and energy as the most valuable asset. Delegate tasks and protect your bedtime.
Thanks for listening and see you next time.
Sources
- Anna: The Biography, by Amy Odell
- Front Row: Anna Wintour: The Cool Life and Hot Times of Vogue's Editor in Chief, by Jerry Oppenheimer