Look, full disclosure. And I said this to someone on Instagram who asked me if it was worth it. I would literally buy a bag of mackerel that was on fire if Anna Wintour gave it the thumbs up.
I truly do admire her – she has helmed US Vogue for 32 years (since the year I was born), which is no small feat, and her reputation for being a hard-ass boss who takes no prisoners... I'm into that. (Mostly because I feel like there are male bosses everywhere doing the exact same things she does and no one makes passive aggressive romantic comedy movies about their work behaviours.)
I was hook, line and sinker for this Masterclass when they found me on Instagram with their 20 million ads. They know how to get me – magazines? Check. An opportunity to learn? Check. AW in her natural habitat, teasing us with 'insider info' and 'never-before-seen' and the likes? CHECK actual MATE.
THE PROMISE
I was seduced by the idea of seeing the real Anna. Notoriously private and closed off to the public, just a glimpse would do. Combine that micro-dream with the slick production and polished graphics of the Masterclass franchise and I would've paid double the cost.
Incidentally, the fee was €100 – which struck me as incredibly good value to learn, well, anything new, from Anna. She's absolutely the most powerful woman in fashion, top five in media... Potential insights from her are hella valuable.
Masterclass, for the uninitiated, is an online learning platform where the best of the best give classes in what they're good at. Aaron Sorkin teaches screenwriting, Steve Martin does comedy, Serena Williams gives away the secrets of her grand slam wins. You can see why people drool.
THE CLASSES
Kicking off, there are 12 lessons, ranging from 'Executing a Vision' to 'Editorial Decision Making' to 'Leading with Impact'. They're between 10 and 20 minutes long each... I won't lie, that disappointed me. I wanted 30 minutes at least per lesson, and don't ask me why I settled on that arbitrary number.
I downloaded the accompanying 35-page workbook and leafed through the pages, looking for... what exactly? Anna's home address for correspondence? It wasn't there, needless to say. The workbook seemed to me to be a bit banal, but I withheld my judgment. I wanted so much for it to be brilliant.
LESSONS... LEARNED?
In the 'Editorial Decision Making' lesson, she 'brings us' to a Vogue editorial meeting. Now, I've been at countless squeaky-bum-time editorial meetings in my time in magazines. This one made me nervous from 5,000 kilometres away.
Luckily for my nerves, I only had to sit through a few seconds of it, learning nothing apart from the fact that Anna's senior editorial team are on the fast route to PTSD by virtue of her very presence, and feeling their tension rising like yeast in proving bread.
At one point in the 'Leading with a vision' lesson, Anna (and have you noticed, she's 'Anna' to me now, pals) advises that you endeavour not to replace an iconic, high profile team member with someone who is a carbon copy. She gives the example of Alessandro Michele joining Gucci – they cleverly didn't seek an exact replacement for his predecessor.
This advice was somewhat misplaced for most people, I think. I don't know about you, but I don't operate my sole trading business with such lofty standards. Although when I next replace a staff member (Maisie? My dog?) I will make SURE to phone Alessandro Michele first. He's nothing like her.
There's also a piece about 'creating a compelling guest list' which is in the episode about organising the Met Gala. I dutifully, hurriedly noted down: 'COMPELLING GUEST LIST'.
Okay. So, what? Next time I'm organising the Met Gala I'll make sure I have a good celebrity cross-section? Or was Anna trying to tell me, in the subtext, to create a compelling guest list to the GROHND event that is my very existence? Not to go full Carrie Bradshaw on your asses, but... I couldn't help but wonder.
THE CONCLUSION
For the most part, the advice gleaned was predictable. The faux-intimate anecdotes were nothing a fan of Anna's wouldn't have heard before.
She rehashes tales of her morning routine (which everyone and their mother has heard at this stage – tennis at 5am, Starbucks and at her Manhattan desk by eight...) and a story about a chance encounter with a male fan of the magazine on a plane – you could smell the first class leather through my screen – who inspires her to break The Rules and put Madonna on the cover.
Wading through the PR spin and pushing through the perpetual distraction that is her glut of antique rivière necklaces, here is what I did learn:
Take risks, innovate always, or progress is impossible
Don't be led solely by data, let it guide you, but not control you
Stop hearing 'no' and thinking about what you can't do
Immerse yourself in culture, books and film to bring out your own creativity
Make mistakes, learn from them
Building strong interpersonal relationships is the best way to succeed at anything
Give credit where it's due and always let the experts do their thing
One part of the Masterclass I genuinely enjoyed and was intrigued by was the episode where she goes through old Vogue covers, talking through her thought process on each. It's vague, granted, but I did enjoy it. She doesn't exactly break down cover lines and talk about drawing readers in, but I get the distinct impression that she doesn't even remember operating at that level.
I did feel she was being honest about her stance on standing up for what you believe in (Vogue came out in vocal support for Hillary Clinton when she was running for president) and to give back – although it's probably fair to say her personal thoughts on what it means to 'give back' might be somewhat skewed.
The funniest part? At one point, she delivers a soliloquy about how important it is for leaders to be accessible, open, approachable. She REALLY digs in on this point. I found myself thinking... Wow. Maybe she *is* super approachable to her staff? Maybe we, the public, aren't welcome, but her staff, her valued team, can rock up to her to show her pictures of their pets or their latest TikTok recording at any given moment?
But then, she laughs to herself. She mumbles something along the lines of "at least I hope I am..."
SHE KNOWS SHE'S NOT APPROACHABLE. Come on, Anna. You're female Hades.
SO, IS IT WORTH IT?
Is this Masterclass an attempt to place Anna Wintour more firmly into the Zeitgeist? Are we just guest stars, giving piecemeal funding to an extended episode of the incredibly staged Vogue 73 Questions series? It seemed that way.
It felt like The September Issue reimagined: Ostensibly, a real deep dive into who she is, what she knows and her apparent willingness to share both. In reality, it was an exercise in reputation management, showing how forward-thinking, how 'woke' Anna is, how Vogue is moving with the times (I'll halt my eye rolling for a moment in order to type this final paragraph).
This won't be a career-changing €100 investment for anyone. I feel I would have gotten better, more practical and more insightful advice from one of her senior editors, one of her groundwork team, of which there are many. This served as yet another building block in the formation of her mythical creature-like status.
She's exclusive. She's better than you. She's not for everyone, and Neither. Is. Vogue. So there.
If authenticity was the goal, Anna and the Masterclass franchise failed on this occasion, for me. But would I still buy a bag of flaming faecal matter from her? Absolutely yes.
A.