“Recently, this insecurity recently lead me down a deep dark rabbit hole… To a free trial of Masterclass where I watched Anna Wintour’s Masterclass on Creativity and Leadership. ”

Being a private person, but also having an ego that demands that you share your thoughts with the world, is a very tricky spot to be in, especially when you want people to care about what you are writing. In our society, it's not just about putting your art out there; people want to connect with the person behind the art. As a filmmaker, it's not enough to just make films; you're expected to be a "personality," to be authentic and accessible (or at least perceived that way).

Many people claim to want authenticity. If that were true though, influencers wouldn’t use filters, people would genuinely mean it when they asked strangers how their day was going, and make-up sales would plummet (not because I don’t think make-up and beauty isn’t a form of self expression, but because many people use it as a shield instead of an enhancement, but I digress…). The masses don’t want authenticity. They want authenticity-lite; an aesthetically pleasing version of what they feel to be an aspirational life.

Despite my efforts to keep my private life private, people are quick to slap labels on me based on their assumptions. Whether it's my sexuality, dietary choices, or political beliefs, strangers seem eager to categorize me without knowing the first thing about me. (If I had a dollar every time someone assumed I was a vegetarian and/or a lesbian, I’d have, well, more money than I do now.)

Recently, this insecurity recently lead me down a deep dark rabbit hole… To a free trial of Masterclass where I watched Anna Wintour’s Masterclass on Creativity and Leadership. While I admire Anna Wintour’s career, I realized that I know nothing about her: she is either a genius when it comes to personal branding, or incredibly lucky.

Wintour is a projection. With her trademarked bob, sunglasses, and unmoving face, she has become a Hunter S. Thompson-esque caricature. She publicly reveals very little about herself (next to nothing, actually) but surrounds herself with talented and influential people. Anna herself, though, is a blank slate. You can project whatever you want onto her, and in your reality, you will be right because she’s not going to argue back with you. She won’t engage online, give lengthy interviews, or ever have her own podcast. She is whatever you think she is.

Her Masterclass didn’t share a single personal anecdote or reveal anything about her as a person. Instead, it boiled down to “be born with good taste, and surround yourself with talented people.” (I’m very glad I didn’t pay for the class.) I am not sure if it is the reason for her success, or perhaps has happened in spite of her success, but Anna Wintour’s true talent lies in her ability to remain an enigma, allowing others to interpret her however they want.

While Anna Wintour’s Masterclass didn’t teach anything it actually said it would, it did, however, help me understand that being a private individual who also wants to share her thoughts with the world isn’t impossible, but it is a challenge. If you ever see me adopting a personal uniform and becoming a caricature of myself, you’ll know why.

Ashley Good

Balancing Privacy and Authenticity