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This page shares my best articles to read on topics like creativity, decision making, strategy, and more. The central questions I explore are, “How can we learn the best of what others have mastered? And how can we become the best possible version of ourselves?”

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Daniel Scrivner

Annie Leibovitz's Ten Most-Asked Questions

The following Ten Most-Asked Questions originally appears toward the end of Annie Leibovitz's book At Work. She covers everything from her favorite photograph, to her thoughts on film vs digital, to how she puts people at ease while photographing them.

Annie's Ten Most-Asked Questions

What advice do you have for a young photographer who is just starting out?

I've said it a million times that the best thing a young photographer can do is to stay close to home. Start with your friends and family, the people who will put up with you. Discover what it means to be close to your work, to be intimate with the subject. Measure the difference between that and working with someone you don't know as much about. Of course there are many good photographs that have nothing to do with staying close to him, and I guess what I'm really saying is that you should take pictures of something that has meaning for you. When I was a young photographer at Rolling Stone, I learned that what I did mattered. This may have been because I was published, but whether you're published or not, you have to care about what you do. You might even seem to be obsessive about it.

What's your favorite photograph?

I don't have a single favorite photograph. What means the most to me is the body of my work. The accumulation of photographs over the years.

Who's the most difficult person you've ever photographed?

The difficulties usually don't have much to do with the subject. What causes problems are things like the weather. It's too sunny or too dark. You haven't finished shooting and the sun is going down. If it's a big production, you might have a bad hair person. Bad makeup. The strobe doesn't fire fast enough, or doesn't fire at all. Those are real problems. But there certainly are people who are a pain to work with. I'd be crazy to name them. You can't be indiscreet in this business. That being said, in my experience the most difficult people are the people who have been in show business the longest. Especially those who have been in show business since they were children. Not all of them, of course, but some of them go off the edge. They've been catered to for so long that they have a very poor sense of reality.

How many pictures do you take?

Certainly fewer than I did when I was young. But I don't worry about it. It varies. It takes what it takes.

Are you happy with the move from film to digital?

I remember when Kodachrome II was phased out in the seventies. A lot of photographers bought cartons of it and stored it in their refrigerators. But the bottom line was that it was gone. Digital is here whether we like it or not. You can't fight it. In the beginning, I let the process take over. Productions were incredibly complicated. The rhythm of the shoot changed. I had to explain to the subject that I was going to go across the room to look at the picture on the monitor, which seemed a little rude. But now I don't usually have a monitor on set, and if I do, I don't look at it very often. We just use a laptop, and I'm tether to it. I don't even look at the back of the camera very often. We're almost back to the rhythm of shooting with film.

You can photograph the night with digital. Darkness. I use much less light now. Less strobe. You can see more. The downside is that the pictures can look a little crude. There's almost too much information in them. It's a new language that needs to be translated, and I think that is only going to improve. Think of early flash photography. Things were lit up in a harsh way in the beginning, and then we learned how to control the lights. Digital produces a look that seems appropriate for this moment in history. It's distinctive.

Digital was born for reportage. It's terrific for working spontaneously. I can go on the road with less equipment. I'm not carrying bags of film around. And I can shoot at unbelievably high speeds. We used to shoot at the lowest ASA possible, to avoid having grainy pictures. Higher speeds are rendering images much better than they used to.

How is photography a celebrity different from photographing a regular person?

The fundamental difference is that you have a pretty good idea who the well known person is when you meet them. They've been photographed before. You learn a tremendous amount about a person from their visual history. This is useful, since famous people are almost always busy, and you have to be practical about how much time you're going to get with them. Photographing well-known people has built-in logistical problems. There are often quite a few other people with an interest in the outcome of the shoot. It's not always fulfilling work trying to meet the expectations magazines have about movie stars, for instance. It's not the movie stars themselves who create the difficulties. Most of them are fairly normal people.

Where do you get your ideas?

When I was young, I never knew when to stop. I could never tell what I had. I was afraid I was going to miss something if I left. I remember working with the writer David Felton on a story about The Beach Boys and being surprised that at a certain point he just walked away. He said he had enough material, which seemed incomprehensible to me. What did he mean he had enough? How could he even think like that? I thought that if you kept doing it, it would get better and better.

As I became more experienced, I began to understand that someone who is being photographed can work for only so long and that you shouldn't belabor the situation. Something is either going to happen or it's not going to happen. It's not going to suddenly turn into something else. Or very rarely. What does happen a lot is that as soon as you say it's over, the subject will feel relieved and suddenly look great. And then you keep shooting.

There are times when I just can't get what I want. I sometimes think I get maybe ten percent of what I see. I can be very frustrated, for instance, by natural light. Sometimes the light on someone looks incredibly beautiful but it just won't translate into the photograph. It won't look the same. Photography is limited. It's an illusion of what's going on. Basically, you're never totally satisfied.

How much direction do you give?

A lot of the direction of the shoot takes place before the subject comes in. This is certainly the case with set-up portraits. By the time the subject arrives we've figured out what is possible for them to do. You set the stage for them. Once they are there, get like to have some direction. They like to be at least told that they're doing all right. I forget about that from time to time.

A lot of my work is post-decisive-moment. It's studied. A kind of performance art. It would be nice to be more spontaneous, but circumstances don't always allow that. There is often a limited amount of time, and certain goals. Nevertheless, as prepared as you are for one thing, you hope that something else will happen too.

How do you set people at ease and get them to do the things that they do in your pictures?

I never set anyone at ease. I always thought that was their problem. Either they were at ease or they weren't. That was part of what was interesting about a picture. Setting people at ease is not part of what I do. The question assumes that one is looking for a “nice” picture, but a good portrait photographer is looking for something else. It might be a nice picture and it might not. I know, however, that I do set people at ease because I'm very direct. I'm there simply to take the picture and that's it.

Most people don't like having their picture taken. It's a stressful, self-confrontational moment. Some people are better at it than others. I work best with people who can project themselves, but many people can't do that. Or they don't want to. They don't feel good about themselves. Or they feel too good about themselves. I'm not very accomplished at talking to people, and I certainly can't talk to people and take pictures at the same time. For one thing, I look through a viewfinder when I work. Richard Avedon seduced his subjects with conversation. He had a Rolleiflex that he would look down at and then up from. It was never in front of his fact. Most of the great portrait photographers didn't have a camera in front of their faces. It was next to them while they talked.

The classic anecdote about Avedon getting what he wanted from a sitter is the one about him going to photograph the Duke and Duchess of Windsor. They were great animal lovers. They doted on their pugs. Avedon set up the portrait, talking all the while, and just before he took the picture he told them a story, completely untrue, about how on the way to the sitting his taxi had run over a little dog. That broke their composure. He got the famous portrait of them looking anguished.

Maybe if I live another fifty years I could do that. You have to admire it, though.

I think the only form of seduction I'm capable of is the assurance that I'm a good photographer and that we're going to do something interesting. I've never asked anyone to do something that didn't seem right for them. And I don't ask them to do something for no reason. There's always some thought before my pictures. I throw out several ideas and see what the subject wants to do. When I photographed the performance artist Rachel Rosenthal, for instance, I gave her three or four ideas. The last one was about being buried in the sand in the desert. That's the one she got excited about. I also sometimes ask a subject if they have ideas. The portrait of Cindy Sherman was her idea. I just brought it to life. Realized it.

It's a collaboration. Especially if you're working with an entertainer, an actor, or a comedian. I never make people do anything. But I'm the photographer. It's a photo session. A lot of it is about play. Painting the Blues Brothers blue, for instance. Or giving a subject a role, a fantasy, to act out. I'm interested in getting something unpredictable, something you don't normally see. Even so, when the picture starts to happen, it's often a surprise.

These ten questions and answered originally appeared in Annie Leibovitz's At Work.

About the author

Daniel Scrivner is an award-winner designer turned founder and investor. He's led design work at Apple and Square. He is an early investor in Notion,, and Good Eggs. He's also the founder of Ligature: The Design VC and Outlier Academy. Daniel has interviewed the world’s leading founders and investors including Scott Belsky, Luke Gromen, Kevin Kelly, Gokul Rajaram, and Brian Scudamore.

Last updated
Sep 24, 2023

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