Quick, close your eyes and picture yourself walking down the street in a strange place. You spot a large rather scary looking man, he turns and makes eye contact with you. He doesn’t look happy. The light is perfect, he’s wearing an unusual hat and his face is interesting. It’s a perfect opportunity. His portrait could be that one iconic image you’ve been wanting to make since you first picked up a camera. “This is it!” you tell yourself. But first, you have to ask.

What do you do next? How do you feel? You’re torn between making a great photo and giving in to your fear.
And that’s too bad because people are so fascinating. All are different and none are perfect. Everyone is photogenic. Everyone’s face has a unique story to tell. As humans we are hard-wired to be drawn to faces. But to make a good photo we must connect personally with the individual and that requires asking permission and gaining trust. Yikes.
Fear just walks at your side pretending to be your dear, caring friend.
Once you’re fooled, he takes your hand – and leads you off a cliff.
-Dov Gordon

I’m shy with strangers. The thought of approaching someone I don’t know to ask a favor can make me break out into a cold sweat.
About 12 years ago I started to register for an online portraiture course. Before I clicked “Add to Cart” I reviewed the syllabus and noticed that one of the shooting assignments required me to make portraits of strangers on the street. As I pictured myself doing this, I did literally break into a cold sweat.
I passed on that course and registered for one about street photography instead (no portrait assignments in this one). It turned out to be good thing because it lit the fire that led me to create this magazine.
Since then, I have learned to identify the negative self-talk that caused me to be fearful of rejection, but it’s still uncomfortable. It’s always a struggle for me.
Recently I took a course from Harvey Stein at ICP called Photographing People with Intention and Purpose. It included a street portraiture assignment. This time I was ready and the experience was transformative.
After spending the last 8 years interviewing hundreds of street photographers and getting to know masters like Harvey I’ve learned a lot about how shy people like myself can break through self-imposed limitations and make compelling street portraits.
This article will share some of what I’ve learned in hopes that some of it will help you as well.
Set yourself up for success

Go where people are comfortable with being photographed
Breaking the ice is much easier when you are in a place where it’s not unusual to see people making pictures. At street fairs, sporting events and farmers markets, you see people taking photos all over the place. Someone with a camera is not a surprise and people are more comfortable being photographed.
Photo ©2011 Harvey Stein

Find places where people are waiting or relaxing
You’re not going to have much success stopping someone rushing to catch a bus to make their photo. Instead, look for places where people are already sitting still. Places like bars, bus stops or stairs. For example, the front steps of the Metropolitan Museum of Art (the Met) in New York is an excellent place to hang out. In Washington DC, a great spot is the steps of the Lincoln Memorial or any popular museum or monument.
Look for the ideal situations: parks, bus stops, metro stations, stairs in front of churches where people are usually waiting or relaxing.
Parks, bus stops, subway stations, places where people hang out.

Have your camera visible and ready
First you want to make it clear that you are a photographer. What better way than having your camera out, around your neck or at your side.
Also have your settings pre-set and ready to go. You will have only a short time to make the photo so you don’t want to fumble with the camera when it’s time to shoot. Bottom line, know your camera. In golf they say never try a shot on the course that you haven’t already practiced. Same thing applies to photography.

Choose people already in the shade
If it’s a bright sunny day try to shoot in open shade. Making your subject face the sun causes them to squint, shadows are super dark and it’s easy to blow highlights on the face.
If you find people already in the shade you don’t have to move them around…which you should keep to a minimum anyway.
Know what you want to accomplish before you approach you subject
Light direction, quality and quantity
Ideally you will shoot in the open shade, but that won’t always be the case. So assess the lighting situation before you begin to know what you want to do from the beginning.
When you have that already decided, it’s easier to focus on your subject and you can move quickly and decisively when giving them direction.
Type of shot
Before you shoot decide in advance what types of shots you want. Head shot, 3/4 shot, environmental, or something else?
Don’t wing it!
I know shooting on the street is chaotic and you can’t know what is going to happen in advance. But you can still have much of the decision making done in advance to remove as much uncertainty as possible.
Doing this will make you more confident and relaxed which will help you gain the trust of your subject.

Make a personal connection with your subject
The best portraits are made when the photographer has made a personal connection with their subject and earned their trust. The personal connection is secondary to the gear you use or technical decisions you make.
As much as you want to make that one “iconic image” before you die, photographing people isn’t about you. It’s all about them.
The closer you get emotionally as well as physically the better your photographs will be.
Remember all of us, no matter who we are, are tuned into the radio station WIIFM or what’s in it for me. The more you understand that and the more you act on it the better your photos will be.
Odds are 2 to 1 that your subject’s thoughts are inwardly focused. It’s how we’re made. They don’t give a shit about you and how much you want that killer photo. So get over it and make it all about them. The more you do that, the more they will give you. It will be more likely that they will trust you and give you and honest expression. But you only have a few minutes.

What’s your purpose?
Having an understanding of what you are doing, why and believing in the project goes a long way in building confidence. When you are confident in your project, it shows.
Be clear in your own mind about what you are doing and why. And be confident in not only yourself but the project you are working on. The more confident you are the more it will show. On the flip side, if you are unsure and doubt yourself, that will show as well.
If you don’t have a project, create one now. Give it a name and use it.
Photo by Frank Blazquez

The Approach
How do you approach a stranger? I can’t tell you what to say or how to look. But there are a few rules of thumb.
It’s not about you, it’s about them.
Photo by Glen Cameron

Be friendly and polite
If nothing else, just be nice. If you smile naturally do it. And maintain eye contact. This isn’t time to look for the right light and a good background. Save that for after you receive permission.
Photo by Ashley Tillery

Know your opening line by heart
DON’T WING IT (I know I said this before, but it bears repeating).
Prepare a short opening sentence that tells your subject who you are, what you want and why. Keep it very short and to the point. If there is something distinctive about them, give them a sincere compliment about it.
It has to be in your own words and come from the heart. For example:
“Hi I’m Bob, I’m a local photographer doing a project about XYZ and I couldn’t help but notice your hat (or your tattoos, your smile, your eyes, your glasses, whatever). Is it OK to make a couple photos of you?” Something about the person caught your interest. Be sincere and tell them. I find it helpful to break the ice and chat a little before even touching the camera. It’s fun to meet new people and you might make a friend.
Photo @ Copyright Ibarionex Perello

Be prepared for rejection
People will say no, so be ready for it. In some places, you will be rejected very little and in others quite a lot. It’s not personal, so be polite, thank them and move on. And don’t try to change their mind.
Photo by Andy Hann
This is part one. In the February 2021 issue we’ll continue with making the photograph.
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