The Devil Wears Converse

A few summers ago, just as I was beginning to publish Greenwoman, my first magazine venture, I watched the documentary The September Issue with my teenage daughter Lily. The film is a behind-the-scenes look at Vogue editor-in-chief Anna Wintour and her staff during the creation of their fall fashion issue, the most important issue of the year. While I’m not a huge fan of haute couture (Lily is), I appreciate the art of fashion, and I’ve always loved Vogue’s articles on non-fashion subjects like art, celebrities, and politics.

I’d also enjoyed the film The Devil Wears Prada, which is the memoir of an intern who worked for Wintour. The film left me with a few preconceived notions. Specifically, Wintour was portrayed as 1) shockingly insensitive to others’ feelings, in particular, her employees’, and 2) ruthless and boundary-less when it came to using employees for personal situations. If you think about it, those were her only “crimes,” but for a woman, they are felonies.

Watching The September Issue back then, I didn’t come away with a negative impression of Wintour. Far from it; I was in awe of her abilities. She seemed a soft-serve version of the icy Prada-lady, and none of the thorny employee boundary issues came up. While she was the star of the documentary (and of the magazine), I was not surprised that I found myself identifying strongly with Vogue’s Art Director, Grace Coddington. Coddington, a brilliant photographer and stylist, was fun, impish, and opinionated. She didn’t care at all about being a fashion plate herself. Unlike other Vogue staff members, she defiantly wore her signature black clothing, which Wintour had declared “out,” and comfortable sandals instead of de rigueur high heels. Most admirably, Coddington was fearless and vocal in questioning Wintour’s editorial decisions. That is what I identified with most—that questioning of authority, as it was a personal trait of my own that I held dear (even as it often got me into trouble).

Coddington would take a series of exquisitely beautiful photos, and Wintour would choose several and leave many others on the cutting room floor. Coddington would become upset, but Wintour would ignore those emotions, feeling secure that she’d made the correct decisions. Yet through all of this, the two would reach a sensible compromise.

This dance between the “establishment” and the “movement” fascinated me. I saw how those forces work against (yet ultimately for) one another. The establishment always seeks to thwart evolution; the movement always pushes for it. That dynamic is clear in the film. Coddington (and other artists) push forward and test the boundaries; Wintour reigns them in, yet she also engages in the process (and the ultimate progress). She evaluates and edits that forward push, serving as both establishment and movement.

My surprise was to see my own shift. It wasn’t long before I began to identify with Anna Wintour—though I actually shook my head while typing those words, as it is such a newly emergent part of my personality.

Here’s how my sympathy for the devil came about. Now I’m doing basically what Wintour does, though obviously at a much different level. The point is, I’ve become the person who must make decisions. As the editor-in-chief of my own publication, I’m answerable to everything, which is, ultimately, the success or failure of the magazine. As this enterprise has progressed, I’ve come to the point where I’ve learned a single all-important lesson: There’s no time to mess around. The magazine comes first. Emotional stuff gets in the way. Decisions must be made quickly and with a clear head. If something isn’t working, it must be fixed, or dispensed with, immediately.

This is tough. In the last month, I’ve had to 1) reject a small piece of art that I asked, as a favor, to be created from someone I didn’t know well—and then deal with a mini-temper tantrum from the artist; 2) find another writer, at the eleventh hour, to replace one who couldn’t fulfill her obligation; 3) make the decision to try to design the entire magazine myself, adding more weeks of training and work to my already overloaded plate, not to mention setting the publication date back a few weeks; 4) consider advice from a person notable in the garden/education field who wrote me suggesting that I should abandon my idea of a subscription print magazine altogether and instead create a free online publication (having faith the advertisers will come); and, most harrowing, 5) go through a grant interview in which I had to lay my last 15-20 years of a life immersed in art, gardening, and writing soul-bare in order to try to make this project financially easier on me and my family.

All of these trials had emotional costs, and my decisions had to be made quickly and on a single criterion—what I believe is best for the magazine and, by association, me. I surprised myself on how efficiently and quickly I met each challenge. As I told a friend, I could not have done the things I am doing now ten years ago.

The only trial that really shook me was the grant interview. Although the people conducting it were wonderfully friendly and genuinely engaged in my story, I have never felt so naked and vulnerable as then, sharing my hopes, dreams, motivations. The hardest part was doing it in a context that felt, ultimately, like begging. Please approve of me, what I’ve put my heart and soul into for the last two decades! Please consider my vision worthy! Won’t you slice off a little piece of that tasty philanthropic pie for my humble art? Later that day, I wept while working in the garden, feeling angry at what I perceived as failure—that I didn’t have enough money myself to do things without asking for help, feeling a prideful pain that I had to expose my soul and ask for my worth to be validated.

My anger was soon replaced by defiance. At one point during the interview, I was asked if I’d “accept less than I requested.” Immediately I chirped, “Sure!” Later I thought about the many hours of work I’d put into applying for that grant and how many hoops I’d jumped through. Now there would be more weeks of seemingly endless waiting around, and then if I got the award there would be more requirements, more hoops. My friend Edie once joked that we had the same personalities, we were like the little mouse that gives the hawk the finger just as it’s about to be swooped upon and devoured. Hence my next thought: If I don’t get what I applied for, well, then, I don’t want any of it. It’s not worth it.

I know I may happily eat humble pie regarding that little proclamation if I have the opportunity. It won’t be the first time. Whether it would be selling out, or wisdom, or a bit of both, I’m not sure. What I do know is the very next day, I went to the bank and took out a loan—and I felt better.

Last week, my horribly unfashionable old pink Converse sneakers were showing their wear. Faded, full of holes, unfit for wearing in public, though I was still doing just that. I have a weird attachment to this brand of shoes; it’s not just comfort—they also symbolize the girl-me who lives strongly still, the girl who got her first pair (white) at age 11. They represent the whole rock ‘n’ roll-Coddington-appetite for defiance. Lily, out shopping with me and somewhat scandalized by my lack of good taste (her inner Anna Wintour always in dominance), asked me when I gleefully spotted a new pair for $25: “Mom, you’re almost 50, when are you going to stop wearing those?”

“When I’m 90.”

At home I showed my husband my new shoes and took the old ones to the trash. He asked, “Aren’t you going to save those, to garden in?”

“Hell no,” I said. “I’m wearing my new ones to garden in.”

Anna Wintour is rising, but I’m glad the Grace in me is still going strong.