I Lived “The Devil Wears Prada”

“There you are Barbie, how many times do I have to scream your name?” Image from BarbieFantasies on Flickr.

We all love The Devil Wears Prada. Few of us get to actually live it.

I process the weekly shipments at my bar. Every Thursday we get liquor by the case and boxes full of beer and fruits. I open each case and count every bottle into inventory, restock the leaky walk-in with limes and Heinekens, putting extra bottles in storage until needed, all while listening to music of my choosing (I’m on a Faith Hill kick lately). Big shipments take more time to unpack. Festival shipments like before Pride or Folsom Street Fair take extra hands to put everything away. It’s a simple task with a straightforward goal and when I’m done, it’s over. 

Now and then it hits me sideways that I once earned twice as much per hour. It happens when I hit a low, usually in the middle of or after a busy shift. I’ll find a pint of piss from someone unable or unwilling to go inside and think, “I was somebody.” At worst I’ll browbeat myself for failing to match my former boss’ impossible standards. Then I remember who my boss was, how the job overtook my life, and I fill the ice wells again.

This is Part One about how I fell into, and out of, my very own Devil Wears Prada experience.

I think every fan, when they watch The Devil Wears Prada, places themselves in Andy’s (Anne Hathaway) chunky shoes. It makes the upgrade to Jimmy Choos feel like a graduation. The cocky among us think, given the opportunity, they’d excel where Andy failed. That’s assuming you get a true Miranda, a boss with the business acumen to back up their tyrannical behavior.

Owner and founder of San Francisco interior design firm Ħażin totali, Massimo Calvizi thought himself a Miranda. He’d given himself some big heels to fill. Played by Meryl Streep in the film, Miranda Priestly is the best in her field. It’s why her career spans so many years, and why she can’t be replaced (f*** off, Jacqueline!). By hiring Andrea “Andy” Sachs, she’s “taking a chance” on someone from outside the fashion world. I hoped hiring this smart, fat girl was one of Massimo’s intuitive decisions, the kind that ultimately boosted business. His wealthy appearance and lofty title seemed the result of good choices, not impulsive ones. 

Similarly, I hoped leaving Broke-Ass Stuart would pay off in more ways than one. I had no idea what “content writing” meant initially. Turns out I’ve been doing it most of my working life. If you ever memorized selling verbiage for a retail job, you’ve engaged in content writing. It just never made it to the page, and why would it? The “content” doesn’t matter. Unlike my master’s thesis or the writing I did for Stu, updating Massimo’s website was strictly for the paycheck.

And it was a substantial paycheck. I started partway through the pay period and still received a $1,700 direct deposit. All for revising maybe three pages of stuff. Another Andy parallel: I didn’t respect my boss’ work. “They all act like they’re curing cancer,” Andrea complains to on-screen boyfriend Nate (Adrien Grenier). Massimo’s spending habits felt like watching someone leave a faucet on. The whole time I worked there, a $22,000 rug lay curled up against the office’s wall. His high standards resulted in sunk investments and thousands of dollars lost. From discarded setpieces to rehashed photo shoots to overtime for his moving crews, Massimo liked throwing money around.

I felt most like Andy Sachs those first few weeks, rushing for trains, grabbing coffee on my way. I was building a Spotify playlist that cut out in the tunnels between Van Ness and Castro Stations. Imagine the Prada soundtrack fluffed with personal favorites, except mine included KT Tunstall’s “Suddenly I See” (such a banger!). If in fact this was my big break, I may as well lean into it, only it didn’t feel that way. A big break no doubt, but mine? I hoped this feeling was temporary. In the meantime I would lean on someone else’s soundtrack until I could inspire my own.

If Massimo is Miranda, the role of Emily Charlton (Emily Blunt) goes to the serious, fit blonde I’m calling Florence. “Remember, we have totally different jobs,” Emily says to Andy on her first day. “You get coffee and run errands, yet I am in charge of her schedule, her appointments and her expenses.” Massimo’s unpredictable schedule was always a thorn in Florence’s side. I saw how he got under her skin when she took his calls, cancelling this, rebooking that. Still she made it work, every time. He also tasked her with haranguing clients for payment and keeping track of growing interest on late ones. Florence’s job was indeed totally different, her life primarily work, her Paris any tropical island where Massimo needed a pal. 

One day I basically asked her to blink twice if she wanted me to get her out of there.

“Look, this isn’t The Devil Wears Prada,” Florence preempted (!). “I know he can be a lot, but he’s got a talent. You’ll see.”

Despite how demanding Massimo could be, Florence insisted he was a smart, creative boss. It’s why she’s Emily, not only because she was second in command. She was every bit as crucial to her boss’ life as Emily was hers, maybe more. At the end of the day, Florence kept Ħażin totali alive, not Massimo. I’ll always picture her hunched over her desk like Rodin’s Penseur, forever sorting discrepancies between paper and digital calendars. 

That leaves Stanley Tucci’s iconic Nigel Kipling, the gem of Prada’s perfect cast, to Massimo’s unsung workhorse, Gia. Gia quit well before I started, having submitted her two-weeks notice at least six months prior. Like Hades, Massimo wouldn’t release her. He depended on her car, her quick thinking, her inability to say no. Similar to Florence, Gia admired Massimo. It’s how he got away with scapegoating her for his blunders and insulting her Asian heritage (“A driver almost hit me today, one of your people.”). Still she came to work, every day. I envied Gia the least.

These were the people I found myself with Monday through Friday, 9am–5pm, all expecting my allegiance to Massimo. The thing was, I was still waiting to be impressed. I didn’t think of him as Miranda, and that was a problem. He possessed her attitude with seemingly none of the other qualities—keen instincts, inimitable style, unmatched originality—that almost justified it. I would’ve even loved a showdown like the infamous cerulean sweater scene, anything to shake me into respecting him. As he lost the firm more and more money, pretending he was good at what he did grew increasingly difficult.

This is where Andy Sachs and I begin diverging from each other. While hers became a story of upward mobility at the cost of her morals, mine did not. That’s because she was hired to be Miranda’s assistant, whereas Massimo hired me to be his copywriter. Nothing in my contract said I’d be going downtown after work to fetch his tailoring from a hostile Ukrainian lady. Not one clause stipulated that I’d be cleaning and reorganizing his office. Had he been forthright about his desire for a lackey, we might’ve worked something out. But I sacrificed my last BAS party to get a revision done in time for Massimo’s birthday party. He ignored me the entire time, disappearing to the gay bar’s tiny bathroom with gay friends every twenty minutes.

It wouldn’t be long until the Prada fantasy came crashing fantastically down. 

Thanks for reading. Be sure to return for Part Two!