Olivia Wilde, Issue 41, Editor’s Letter

When I was a young, struggling freelance photographer the Internet may have been around, but the idea of a digital portfolio was just a gleam in Al Gore’s eye. Things were much more tactile in those days, and if you wanted anyone to see your pictures, you had to print them, mount them, bind them, and deliver them to said anyone.

This was in the early ‘90s when your portfolio, or “book”, was your calling card, and the idea was to get it in front of magazine photo editors, art buyers and art directors in hopes that they would give you an assignment. When I first started out, my goal was to work for the big New York magazines, Vanity Fair, Rolling Stone, Time, Esquire, Entertainment Weekly, and The New York Times Magazine being a few of my main targets. The way it worked was all of these publications had “drop off days”, when a photographer could drop off his book for the art director to look at – drop it off Tuesday, pick it up Thursday. That’s how things were done, and it was a common sight to see a pile of oversized black portfolios haphazardly stacked in the corner of an office, awaiting the Magic Eye of Fate. I remember walking into a few offices early in my career and getting the feeling that none of those books were going to be opened, or if they were, it would be at the end of the day, resented for being the black blockade between the art director and her desire to get out of there for the night. In my mind, it was a terrible system, and I decided to have none of it.

But let me back up. Most of these offices were in New York, and I was in Los Angeles. I was also broke, which meant I could barely afford to make one portfolio. Let’s consider the costs: My book was handmade (by me) out of a custom metal box lined with wood to snugly cradle a stack of matted 8×10 chromes. The thing weighed a ton, and was not fun to ship. For those of you born after 1980, chromes were slides, and in my case, really big expensive ones. They were made from “dupes”, which were photographed duplicates of original slides or prints, which meant the process was not only costly, but took weeks to do. My book had about 50 images in it, so I’m guessing I spent about $1,500 in 1994 money to make it. All to say, I didn’t have the luxury that some established photographers enjoyed of having multiple books in rotation for “drop off days”.

So I decided I was going to do things a little differently. I scheduled a trip to New York and began making calls to art directors and photo editors. I explained that I was in town for just a short time, and the only way I could show my work was in person. But I also made sure to let them know I was coming all the way from Los Angeles to meet with them because I so desired to work for their magazine, and truly loved the work they were doing. All that killing with kindness and cajolery garnered me a few appointments, and once I’d scored the first one, I’d use that information on my next call: “I’m sorry, I really can’t drop the book off, because I’m meeting MaryAnne Golon at Time magazine at 3 p.m., but I can pop over right after that.” One man’s small fib is another one’s hustle, right?

And it worked! I started to get appointments. Sometimes I got horribly lost, or miscalculated the time it would take to transfer subway trains. In an effort to save cab fare, I’d find myself sprinting down 6th Avenue in my good shoes, racing the clock and swinging this heavy metal box like it was an attaché case containing critical nuclear codes. Riding the elevator up to my appointment, I’d try desperately to catch my breath and wipe the sweat from my face before meeting these heretofore-mythical magazine titans to show them my wares.

Don’t ever underestimate the power of a face-to-face meeting. I sometimes feel sorry for young photographers who send a blind email to every possible buyer of photography on the planet with a link to their website. They’re buying hundreds of lottery tickets in hopes of making one connection. When I showed up in a photo editor’s office, I was going to make sure they were entertained. I told stories as I flipped through my pictures, trying to gauge which images were making an impression. I made sure to ask for advice, which always got them talking, and extended the meeting. I even coerced a few into grabbing a drink with me. As inexperienced as I was, I guess some part of me understood even back then that while my pictures hopefully spoke for themselves, these people weren’t hiring my photos, they were hiring me. They should get a sense of who I was; I wanted to be a colleague, a friend, a collaborator – not a faceless black book in the corner.

On the third morning of that trip to New York, I was riding the subway to a meeting uptown, and feeling pretty groggy. I was sleeping on the couch of a friend of a friend who lived in New Jersey, so each morning I had to walk to the Big Apple bus stop, lugging that godforsaken metal box, just to get started. When my train stopped, I wandered out of the station and up the stairs to get my bearings. I started walking toward a street sign to see which direction I was headed in, and then froze. Both my steps and my unencumbered arm felt strangely light. My metal box! Oh god! My portfolio and my entire reason for being in New York were still on the subway, no doubt speeding their way toward Washington Heights right now. Knowing it was hopeless, I spun around and ran frantically back to the subway and down the stairs anyway. As I re-entered the tunnel, the train was miraculously still there, its doors open. I raced towards it, expecting the doors to close any second. I made it inside, and there, sitting patiently on the floor of the train, was my faithful metal box. Either it was too heavy to steal, or people thought it was a bomb. As the indifferent subway crowds swarmed in, I sat there, almost crying with relief. I was never so happy to feel my arm go numb as I ran back down the street, late for my next appointment.

I think it’s easy to look back fondly on those early years, but the truth is, it was mostly struggle, and certainly not glamorous. But when the phone rang a few weeks later and the photo editor of Entertainment Weekly offered me my first magazine assignment, it felt like I had conquered New York, and nothing could stop me. Granted, the assignment was to photograph a parking space on the Warner Bros. lot, and not a cover, but hey, you have to start somewhere. And that’s another story.