Dear streettogs, I am excited to announce my new free book: “The Street Portrait Manual.” If you’ve ever wanted to learn how to build your confidence approaching strangers, how to direct your subjects, and not make photos that look “posed” — I think you will enjoy this one!

Download:

You can download this book for free below in the following formats:

PDF:

This version has all the pictures and examples:

Text:

This version has only text, no images. Use these files if you want to read the book on a Kindle, e-reader, or if you want to edit, change, translate, or modify the text (as this book is “open source“).

Read more if you want to read the full text online (or save it to a service like Pocket or Instapaper):

The Street Portrait Manual

by Eric Kim

6/5/2015

Introduction to Street Portraits

Street portraits are something close to my heart. When I started “street photography”, apparently it was unacceptable to take portraits of strangers in the streets. It wasn’t deemed “street photography”, and apparently taking photos with permission wasn’t as difficult and challenging as the traditional candid “street photography.”

For me, I have always been an extrovert. I genuinely love human beings, and love being around them. I prefer to interact with people, rather than just being an unattached observer. I like to hear peoples’ life stories, and build a genuine human connection with them.

About 70% of my work is shot candidly (without permission), and 30% of my work is shot with permission.

For me, it takes a lot for me to step outside of my comfort zone and ask to take a portrait of a stranger. It is also scarier than shooting candidly, because there is a chance that I might get rejected.

This is because when you shoot candidly, your subject had no matter of say whether or not they are going to get photographed. The bigger issue with shooting candidly is whether or not they will get pissed off you at you or not.

The part of making yourself vulnerable of shooting street portraits is that they have the option to either say “yes” or “no”. If they say “no”, then you’re out of luck.

Why Write a Book on Street Portraits?

I have written a lot of articles on street photography, but I realize I haven’t talked too much about shooting “street portraits”. You might have a lot of questions like: “What is the difference between ‘street portraits’ and ‘street photography’? How can I make a genuine image that doesn’t look too ‘posed’? How can I overcome my fear of approaching strangers?”

In this book I hope to cover all of these topics. For further resources, you can also check out my “street portrait” videos on YouTube, or even my YouTube video presentation lecture: “How to shoot street portraits.” I know some people prefer to learn via video instead of text, and that is totally cool.

But for me, ultimately I best prefer to learn via reading. So if you’re a bookworm (like me), I hope you enjoy.

What is a Street Portrait?

To me plainly put, a “street portrait” is simply a photograph of a stranger in which you ask for permission.

So what is the difference between “street portraits” and “street photography”?

Well, for me I think there isn’t really a difference. In-fact, I consider “street portraits” a sub-genre of street photography.

For example, let’s consider “street photography” the genre of photography. Under “street photography” we have different branches such as “street portraits”, “candid photos”, “urban landscapes”, and “found objects”.

And how would I define “street photography”? For me, street photography is documenting humanity. I don’t think that “street photography” necessarily has to be candid, nor does it even have to be of a human being. But generally speaking, the best “street photographs” tend to be candid and of human beings (because they feel more “authentic”, and we can relate with them more emotionally).

But for me, I actually think that getting a powerful image that is shot with permission is actually much more difficult than without permission (candidly).

Why is that?

Well, if you’ve ever tried to shoot a “street portrait” (with permission), you might have the biggest problem most photographers face: having the subject look too “posed”.

So how can we crack the barrier of asking strangers permission to take their portrait, and have it look more real, authentic, and non-posed?

What makes a great street portrait?

For me, a great street portrait is an image where I can look into the soul of the subject, and relate or empathize with them on a human level.

There is a saying: “Eyes are the windows to the soul” and I greatly agree. If you look at some of the most famous paintings in history, 99% of the time the subjects in the paintings are looking directly at you, the viewer. The effect this gives the viewer is that the painting is looking directly at you, which makes it more personal, intimate, and sometimes a bit nervous (after all, they are making “eye contact” with you).

If you have ever been in a public space such as inside a bus, a train, or even an elevator, you know how awkward it can be when a stranger suddenly makes eye contact with you. Either you (or the other person) might quickly look away, either feeling embarrassed or awkward.

Eye contact is a very intimate thing. Apparently even a lot of couples have a hard time maintaining uninterrupted eye contact for a very long time.

Assignment #1: Make uninterrupted eye contact with someone you know for 1 minute

If you want to overcome this awkwardness of eye contact, this is an assignment that I learned from my UCLA sociology professor (Terri Anderson) in one of the first days of my Introduction to Sociology course. The assignment was this:

Pair up with a partner, stand really close to them (until your toes are touching), and make uninterrupted eye contact with them for 1 minute. During this minute, you are not allowed to smile, laugh, or talk. Deeply gaze into their eyes, note their eye color, and no matter how awkward it may feel, don’t look away.

When I first heard of this assignment I thought it was crazy. I never did anything like this in my life before. But as I quickly learned, the social rule not to make uninterrupted eye contact with someone is something which is merely socialized. We can break this “rule”.

What I discovered from doing this experiment is that at the end of the day, simply looking into someone’s eyes is just that: looking into someone’s eyes. What I mean by that is there is no need to feel awkward, ashamed, or embarrassed by looking into the eyes of someone else. Nothing bad will happen. The world isn’t going to explode, you won’t die, and everything will be okay.

I know it may be difficult to do this assignment with a complete stranger (for me it was easier, as it was with a bunch of fellow undergraduate students).

So for you, try the assignment with someone you know or love. It can be a friend, a colleague, your mom, or your partner.

Tell them that you’re trying to build your confidence when it comes to street photography (especially when it comes to shooting “street portraits”) and ask them to play along.

So do this: stand straight looking at them, toes touching, and no laughing, smiling, or talking for 1 minute straight.

Based on the students I’ve made do this assignment in past workshops this is what the students discover: that the longer you stare at someone, the less awkward it becomes, and the more comfortable you feel in the presence of the other person.

So consider this first assignment your training to overcome your fear of shooting street portraits, and to build your confidence.

Great “street portrait” photographers in history

When most people think about “street photography” they think of the candid black and white photographs of Henri Cartier-Bresson. They think of people jumping over puddles, bicycles racing down a curved pathway, or a couple having a nice moment at a cafe.

I think those photographs are lovely, but realize that there are also many other street photographers in history who have focused more on “street portraiture” (portraits of strangers with permission).

For example, take Diane Arbus. A female NYC-based photographer, she got intimate with strangers in the streets, often those who were considered “freaks” by the rest of society. She took portraits of giants, dwarves, transgender and transsexuals with great love, sincerity and empathy.

Vivian Maier is another street photographer who has recently hit the spotlight. Roaming the streets of Chicago, she always carried her Rolleiflex in which she shot a lot of “street portraits” of strangers (either candidly, or with permission). While she was interested in capturing “moments” on the streets, it seems that one of her primary interests were capturing interesting people or characters in the streets.

Another photographer who made beautiful “street portraits” who I greatly admire is Richard Avedon. Although Richard Avedon made his living shooting commercial portraits of celebrities, for advertisements, and of other famous people, his body of work: “In the American West” were of just ordinary people in America. They were shot (with permission) on an 8×10 view camera in black and white, with subjects against white backdrops. These portraits are simple, but serene, sometimes unsettling, and deeply peering into the psyche of his subjects.

A street photographer who I greatly admire is Bruce Gilden, and his primary interest is also capturing interesting “characters”. He is also a NYC born-and-raised photographer, and is also an interesting character himself. He talks with a heavy New York accent, and has a lot of attitude and an infectious energy when he’s out shooting on the streets. Although he shoots a lot of “street portraits” of subjects candidly, he also asks for permission as well. A lot of his recent work is on medium-format digital color, where he looks directly into the soul of his subjects with uncompromising sincerity.

Definitions, shmefinitions

Ultimately what I want you to know is this: don’t worry about definitions. To me at the end of the day, definitions are just rules imposed to you by people who think they know better than you. They think that everyone should fit into a nice little box, and that makes life easier to categorize.

I have been part of numerous debates and online drama on what street photography is and what street photography isn’t. A lot of prominent street photographers don’t consider “street portraits” a part of the canon of “street photography”.

But ultimately at the end of the day, who cares? Just shoot whatever interests you. Whether that is a candid photo of strangers jumping over puddles, whether that is up-close-and-personal “street portraits” — it doesn’t matter.

First of all, you are a human being who is interested in life, society, and the well being of strangers and other individuals. Secondly, you are a photographer, because you happen to like to document life before your very eyes. Thirdly, you are a “street photographer,” because you generally prefer to shoot in urban or public areas.

Don’t let labels hold you down.

Why Shoot Street Portraits?

So one of the questions you might have is “why shoot street portraits?”

Generally for me, I find that there are many instances in which you’re walking in the streets, and are just suddenly drawn to an interesting character. They might have an interesting hat, mustache, sunglasses, outfit, mood, or style.

Something compels you to take a photograph of them. It is inexplicable. It is something that is deep in your bones. You don’t know why, but you must photograph that person.

If a stranger is walking on the streets, it isn’t always possible to get a close-up portrait of their face without permission. You might accidentally bump into the person while walking head-on with them, or sometimes you just want to hear their life story.

For me, I have found one of the biggest benefits of shooting “street portraits” is that it gives me the opportunity to get to know that stranger. It gives me the chance to hear their life story, to empathize with them, to connect with them, and hear what they are all about.

These kinds of interactions aren’t possible when shooting candidly.

When to shoot a street portrait?

For me, deciding when or when not to shoot a street portrait depends on my mood. There are certain days in which I feel more extroverted, and walk to talk to everyone who is passing me on the streets. Other days, I feel more introverted, reserved, and contemplative, and I prefer to shoot candidly and from a distance.

Ultimately you should follow your gut. If you genuinely want to shoot a street portrait of someone, don’t think to yourself, “But this isn’t ‘street photography’”. Just go and shoot that person by approaching them, introducing yourself, and asking for permission.

Also another time to know when it is appropriate to shoot a street portrait is when you’re afraid of your subject (or how they might react).

For example, I am really drawn to guys (or girls) who look badass and a little rough around the edges. I am especially drawn to people who look tough and have a lot of tattoos (face tattoos interest me the most). But sometimes I look at people and feel scared— I am not sure whether they are mentally stable, or whether they might punch me in the face if I shot a photograph without their permission.

In these situations, I will go up and ask them nicely. And the funny thing is that often the scariest-looking people can be the nicest people. But you never know until you step outside of your comfort zone and ask.

Assignment #2: Make small talk with a tough-looking stranger

For this assignment, it is all about shattering stereotypes or your preconceived notions of other people.

The next time you’re out on the streets, in a cafe, in a restaurant, ordering something at the store, whatever— and you see someone who looks “scary” or “tough”, try to make small chat with them.

If you live in the states, I usually like to approach tough-looking men and say, “How’s it going boss?” One thing I have learned while growing up is that calling someone “boss” gives them authority, power, and is good for their ego. Not only that, but it makes yourself more humble in respect to them.

Then try to make small chat. It can be about anything. Talk about the weather, the local sports team, or how their day is coming along. Be real. If they respond by saying, “Not much, and you?” perhaps you can respond by saying, “Oh man, my day has actually been pretty shitty. Didn’t sleep much last night, and had to pound 2 double-shots of espresso this morning just to feel like a human being.” It is rare that people open up this honestly, so your subject might be surprised and interested in what you have to say.

If you even have the time, try to learn more about who they are as a human being. Discover where they’re from, what their interests or hobbies are, or what they are passionate about.

Soon what you will discover is that this person who you stereotyped as being scary, tough, or unapproachable is just like you: another human being worthy of love, respect, and openness.

And once you realize that, you will feel much more comfortable approaching random strangers on the street who look tough, you will find out they aren’t so bad.

Worst case-scenario if a tough-guy (or girl) tells you to “fuck off”, take it in stride. Tell them “no problem” and move on— and be happy that you know that you have the strength, confidence, and courage to take negative talk as well.

How to Overcome the Fear of Shooting Street Portraits

In this chapter, I want to talk more about certain practical tips and strategies to overcome your fear of approaching strangers, and shooting street portraits.

Learn to love rejection

When it comes to shooting street portraits, often the fear of rejection is worse than the rejection itself.

For example let me tell a story: When I was a high school student, there was this really pretty girl in my class that I wanted to ask out to a dance. She was way out of my level— far more attractive than I was (nerdy Asian kid).

Anyways, I really wanted to ask her out to the dance, but I was deathly afraid of being rejected. Not only that, but I was afraid of being publicly humiliated when I was rejected. I imagined her rejecting me, laughing at me, and then calling over her hot friends (who would all laugh at me in unison).

But one day I though to myself: “You know what Eric, you’re going to regret not having asked her to the dance, more than you will getting rejected.”

So one day I finally mustered the courage to approach her and ask her to the dance. She rejected me (in a nice way) by saying that she already had a date, but perhaps next time.

Needless to say I was pretty bummed out, but at the same time, I was quite proud of myself for taking a risk. Not only that, but the rejection wasn’t as bad as I imagined it to be.

I think we should apply the same line of thinking to street portraits. The fear of rejection is often worse than the actual rejection.

For example, when you approach a stranger and ask to shoot their portrait, most people generally decline or reject you in a nice way. They won’t say “no” then punch you in the face.

Risk aversion in human beings

As humans, we tend to be “risk averse”, meaning, we hate risks. We hate missing out and losing out. For example, losing $100 feels twice as painful as winning $100 in a casino.

Similarly when it comes to life, being rejected (or the fear of rejection) can be twice as painful as being accepted.

So if you’re afraid of being rejected, don’t feel bad. Rather, congratulate yourself. You are a normal human being.

But if you want to improve your confidence in street photography, you need to learn how to love rejection, and to love risk-taking.

Assignment #3: “The 5 yes, 5 no” challenge

In order to love rejection, I give you the “5 yes, 5 no” challenge.

The concept is simple: you approach a bunch of strangers and ask to make a portrait of them. Then you have to keep asking until you get 5 strangers to say yes, and 5 strangers to say no.

You will find that most people will end up saying “yes”, and getting a “no” is actually much harder than it seems.

I actually have some students who did this assignment in workshops who struggled to get 5 “no’s” by the end of the day. So when they would finally get someone to reject them, they would yell out gleefully: “Yes! Thank you so much for rejecting me, I got a ‘no’ for my assignment!” (while the stranger who rejected them looks at them strangely).

So if you do this assignment, you will learn to love rejection— because being rejected is part of the assignment.

Apparently this assignment can also work in different aspects of life— when it comes to dating and also sales.

Dating is a lot like a numbers game. The more people you ask on dates, and the more people you approach, the more likely you are to get a “yes”. But you are going to have to get a lot of “no’s”.

But think about it this way: if you approached 100 people intentionally trying to get rejected, I can guarantee sooner or later you will unintentionally get at least 1 person to say “yes”.

Similarly, sales in business works the same way. Rather than trying to get 1 sale for your business, try to intentionally get 100 people to say “no”. By working this way, you learn to love rejection, and know that every rejection is a closer step to getting a “no”.

I’ve personally found that the more I get rejected, the more confident I become. Not only that, but I start to learn what not to say when approaching strangers. Then based on my experimentation on approaching strangers on the streets, I start to get more comfortable, and end up getting more “yes’s”.

The fear of looking like a fool in public

We hate being judged. We want everyone to like us, to love us, and to think that we are “normal” human beings. Sticking out can be scary, and when it comes to shooting street portraits, it is a very strange thing to do. After all, how “normal” is it to approach a totally random stranger and ask him/her to take their portrait?

So know that as a street photographer, you are a bit of a social anomaly. And that is okay. Know that the reality of the matter is that when you approach a stranger and ask to make their photograph, you will have other strangers (around you) looking at you strangely, perhaps judging you.

But once again, that is okay.

Being a street photographer you are cut from a different cloth. You are more intensely attuned to the emotions, feelings, thoughts, and emotions of others. You are genuinely trying to do a good and positive thing through your photography— to connect with strangers and other human beings that you feel some sort of connection with.

So be proud that you are different, perhaps weird in a sense.

But how can you overcome the fear of being judged and being looked at as being “weird”? Well— this next assignment will be good for you.

Assignment #4: Do something outlandish

As a confidence-boosting exercise there is something called the “coffee challenge” (learned this from startup mogul Noah Kagan) and it is this: Go into any coffee shop and ask the barista if you can get 10% off your order.

Now I know this assignment sounds a bit crazy. What incentive does the barista have to give you 10% off a coffee?

Well first of all, you can say something a bit out of the ordinary, which makes you interesting, novel, and fun. You can say something like, “I’m a nice guy, you’re a nice guy, and so can you give me a ‘nice guy discount?’” (learned this one from Ira Glass from “This American Life”). Surprisingly, this works more than you would imagine (as a lot of employees can give you a staff-discount).

Or you can try to make them empathize with you. Perhaps if you’re having a pretty bad day, you can say something like: “I know this sounds really weird, but I’m really having a tough day. I’m really stressed out at work; my boss is such a dictator. I need a lot of energy to make it through today. Could you do me a massive favor by making me feel better by giving me a 10% (or any) discount on a cup of coffee?”

I think we make the wrong assumption that everyone out there is cold, heartless, and only in life for himself or herself.

But the opposite is true: we feel happiest when we help others (psychologically proven).

So know that by asking for a small favor, you are giving that person the chance to be kind, generous, and thoughtful. By asking for a small favor, you can actually make the other person happy.

Also this assignment will teach you that it is okay to be rejected. If the barista says something like: “Oh sorry, we don’t do that” — you can just say “Oh no problem” and smile, and order your coffee as normal. No need to feel awkward, judged, or ashamed.

As a street photographer, you are a unique human being. We aren’t like other “ordinary” people — we are drawn to strangers, have a lot of empathy for other human beings, and are genuinely interested in “the human condition”. So what if others might see us as a little weird, stranger, or unusual? It is totally fine — judge yourself positively (and don’t worry of how others judge you).

How Do You Get Interesting Posed Street Portraits?

One of the common questions that I get when it comes to beginning street photographer is: “How do I get a street portrait (with permission) that is interesting— that they don’t look like they are just posing? I want to capture something authentic, and real.”

The way that I respond is this: Just because someone is posed doesn’t mean it is a less “authentic” image. In-fact, the famous image of William Klein’s “Kid with gun” is a posed image. He saw a bunch of kids playing with toy guns, and told one of the kids: “Look tough” — and in that moment the kid gave William Klein the most dirty look, and pointed the gun straight into his face with a look of anger, malice, and passion.

A lot of people ask William Klein: “But this photograph isn’t authentic, it is posed. You just told him what to do.”

But to that William Klein responds: “Yes, I did prod him a little bit, but his expression is something I could have never made up myself. It was a part of his inner-self which truly came out.”

So what you are trying to do when you’re shooting street portraits is to get a little deeper into the psyche of your subject, and for them to show a little more of their inner-self.

Some practical tips:

Wait for your subject to drop their guard

When you’re making a “street portrait”, you want your subjects to drop their guard.

Whenever you start shooting a street portrait, in the beginning your subject will generally be very stiff, uncomfortable, and they don’t look or feel natural.

But the more you talk and engage with them, the less aware they become of your camera, and the less aware they think of you as a photographer.

Sometimes I need to talk with a stranger on the street for about 5 minutes or so before they really drop their guard, and I can capture a more “authentic” look into their inner-life.

The way I get them to drop their guard is just making small chat with them, taking photographs while they talk, or sometimes even shooting with a friend (who distracts them and talks with them) while I make images.

Geoffrey Dyer calls this the “unguarded moment” — similar to the “decisive moment” except it is the moment when the subject becomes vulnerable and drops their outer shell, and reveals more of their own personality.

Ask your subject not to smile

Most people when they are walking on the streets rarely smile. Even though I am a very happy and smiley guy, when I walk on the streets, I am generally stone-faced (as well as most other people).

So having a subject look into your lens, throwing up a peace sign, and smiling doesn’t feel real or authentic. It just looks like another Facebook profile picture.

So this is a tip I got from Magnum photographer Martin Parr: tell your subject that you want a “dignified portrait” of them that is serious. So you ask them not to smile, and to look straight into the lens. Believe it or not, this makes for much more authentic-feeling images.

Practical Tips on How to Shoot Street Portraits

Now to move on, I want to share some other practical tips when it comes to making street portraits.

1. Ask your subject to move to an interesting background

One of the practical tips I have when shooting street portraits is that it is okay to move your subjects.

99% of the time when you approach a stranger, the background will be very messy. You might have random trees, telephone poles, white cars, or random pedestrians that might take away from your subject.

One of my favorite portrait photographers in history is Richard Avedon, and he was famous for taking portraits of celebrities (and strangers) in front of simple white backdrops.

The benefit of having a very simple background was that 100% of your attention is drawn to the subject, nothing else. You had no other distractions.

So if you find an interesting character and you want that person to be the absolute focus of them, you can do this: Before approaching anyone always scan in the background and look for interesting or simple backgrounds. And when you see an interesting subject come towards you, you can introduce yourself, ask to make their portrait, and if they say: “Yes”, then you can ask them: “Oh this background here is really messy. Do you mind moving over a few steps to this wall so we can get a nice and simple background?” The key is also to guide them by using your hand to move them in that direction, by facing your palm upwards and waving towards the wall. This makes them feel like a VIP guest being escorted to the side.

Believe it or not, literally 99.9% of my subjects who say “yes” to having their portrait taken are willing to move a little bit (sometimes even further) to get a simple background.

Also when you are photographing your subject against a background, make sure to look at the edges that you don’t have any distractions poking into your frame.

2. You don’t need to photograph their face

Sometimes people don’t like to have their faces photographed— but most people rarely object to having their hands, feet, or accessories photographed. Some people are just anxious about appearing on social media websites, Facebook, etc.

So if you approach a stranger and they reject having their portrait taken, you can ask them a follow-up question by saying: “Oh, do you mind if I took a photograph of your hands instead? I love your nails, or the character of your hands.”

Most people will then say “yes” — so in these instances, just focus on their hands, their feet, whatever else.

Sometimes making a portrait of a person’s details (not their entire body) is much more interesting. And sometimes a person’s hands can be more interesting than their face.

3. Take a photo of them looking at you / not looking at you

There’s a saying: “Eyes are the windows to the soul”. Sometimes it is better in a street portrait to have someone looking directly at you, and sometimes it is better to have them not look at you.

So when you are shooting a street portrait, you can get best of both worlds: try to get an image of them looking straight into the lens, and another image of them looking away.

So when you’re making their image, you can direct them a little bit. Ask them, “Oh, can I get one photograph of you looking straight into the lens?” Then you can ask them: “Oh, can I get another image of you looking up, down, left, right, etc.?”

Also another practical tip: don’t chimp when making someone’s portrait. This is something that is quite distracting to the subject, and not only that— but it is better to review your photographs when you get home. While you’re photographing your subject, direct 100% of your attention onto them (not the images you are making).

4. Provoke a response

When I am shooting a street portrait, I never 100% know what is going to happen.

I know some street photographers who hate being noticed or detected by their subjects. They want to be more of a “stealth” photographer, or completely invisible.

But I think this isn’t always the right approach— because sometimes by having the subject aware of your presence, you can get more interesting photographs. Meaning— some of the best photographs I have ever made were from my subjects having a response to my presence.

So long story short to make a more interesting street portrait, try to provoke a response.

You can do this in many ways.

First of all, you can try telling a joke. Then if you get your subject to laugh, that is marvelous. Having someone naturally laugh makes a great portrait.

Sometimes you can go darker— you can ask the subject to think about a difficult time they had in their life recently. Then generally the expression of a subject becomes more calm, meditative, and reflective. These expressions often provoke more of a melancholy mood.

In a street portrait I shot recently in New York City of an amazing old lady (she told us she was 84 years old) — I directed her like normal during a workshop. I saw her in the streets, approached her, complimented her on her outfit and how amazing she looked, and started to make portraits of her. I shot about 25 photographs in total, but the best photograph was when I provoked a response in her. There were about 8 other students around me, and she started laughing because of all the attention she was getting. And that is what made the shot.

So think about other ways that you can provoke a natural expression or reaction in your subject.

5. Remember you’ll never see them again

The people you meet in your life and on the streets is a blessing. Chances are once you find someone interesting in the streets, you will never see them again in your life.

This goes back to the idea of risk-aversion: we hate missing out on opportunities, and hate regret in life.

So I follow what Jeff Bezos from Amazon calls: “the regret minimization framework” — I want to live my life as free from regrets as possible.

So whenever I see an interesting subject on the streets, I remind myself: “I will probably never see this person ever again. Will I regret not asking to make their portrait?”

If the answer is “yes, I will regret not taking their photograph”— I quickly shed my fears, approach them (still feeling a bit nervous), and ask to make their image. If they reject me, I still feel a bit bummed, but am glad that at least I asked. So I have no regrets.

6. Sometimes it is good to be a bit pushy

Whenever I approach a stranger and ask to make their portrait, there are some people who don’t give you a direct “no”. They might be a little bit shy and say something like: “Oh, but I don’t look good today” or “Oh, but I am so old an no longer pretty” or something like that.

In these situations you need to realize that these aren’t direct “no’s” — they are on the edge, but just need a little more convincing.

So I tend to be a little pushy, because if I want to make a portrait of a stranger, there is a need for me to capture it.

So I will reassure them that they look beautiful, or that it will only take one second, or that they look really cool.

So long story short, I don’t easily take “no” as an answer.

But ultimately you want to follow your own intuition. If you hear someone say “no” and it is a firm “no” — no need to be pushy. Just thank them, and move on.

7. Be genuinely interested in your subject

As humans we are really good bullshit detectors. It is very easy to tell when someone is just feigning (pretending) to be interested in us to get something from us.

Therefore, the only solution is to be genuinely interested in your subject.

Know that as a street photographer, your job isn’t to just make interesting photographs. You also have a duty to connect with these strangers on the street, to hear their life stories, and to empathize with them emotionally.

So even after I make a street portrait of someone, I generally hang out with them for a few minutes, talk about their day, how they are doing, and anything else going on in their life. I try my best to pay attention, and to listen attentively. I give that subject my 100% undivided attention, then when they need to run (or I need to run), I thank them for their time, smile, and move on.

8. Show them your LCD screen

Another great #protip when shooting street portraits: after making a portrait of someone, show them the back of your LCD screen, and show them what kind of image you made.

Generally a lot of people are skeptical to having their images taken. Not only that, but photography can sometimes be very greedy and 1-sided: the photographer gets all the benefit, while the subject gets none.

But try to make the process a 2-way street. While taking their portrait, show your subject your LCD screen. Then they get a better sense of why you are trying to take their image, and what you see that is interesting as an artist.

Furthermore you can take it a step further by asking them “which photograph of you do you find the best?” Sometimes it can be the most flattering image of them, but sometimes it is the image that they feel is a little more quiet and “authentic”.

You can even ask them to suggest certain poses or expressions.

Have fun, and make them interact with you, and become a part of the image-making process.

9. Offer to email them the photograph

Most people don’t have professional cameras or DSLRs or good profile pictures of them. So realize that when you’re making their portrait, you have the opportunity to give something back to them.

I generally ask people if they have an email address that I can send the photographs to. This excites them.

Another strategy: carry around business cards and ask them to email you. An easy place to get good business cards: moo.com (you can even print your own photographs on the back of the cards)

10. Tell your subject why you want to make their photograph

Sometimes people have low self-esteem and don’t see their inherent beauty.

So when you approach a stranger to make their portrait, tell them why you want to make their photograph, and what exactly you find interesting about them.

I suggest you to be very specific— tell them it is their facial expression, their outfit, their mood, or their look.

And the way you can package this is as a compliment. Most people never get compliments, and to get a compliment puts them in a good mood and headspace.

Spread the love.

11. Realize that just because you had an interesting interaction doesn’t make it an interesting photograph

This is another tough thing you will discover when making street portraits: just because you had an interesting interaction with a stranger doesn’t mean the photograph itself is interesting.

But that is okay and totally normal. Not every street portrait you take is going to be interesting in an objective standpoint. But it is okay, because sometimes the interactions can be more valuable than the photographs.

At the same time— learn to divorce yourself from your photographs. You must kill the backstory of your subjects in your mind and try to be more objective while editing.

A practical way to do this is to wait about a week or two after taking someone’s portrait, and look at it with fresh new eyes. Do you still find it interesting or intriguing from an outsider’s perspective (assuming you didn’t know the backstory?)

You can also ask friends, colleagues, or other street photographers for their honest opinion. Tell them to be “brutally honest” and most people are generally very frank and helpful.

12. Shoot both horizontal/vertical photos

When it comes to shooting street portraits, I think the natural thing to do is just shoot vertical (portrait-orientation) images.

However try to switch it up. While shooting, try to take both horizontal and vertical photos of your subject.

When shooting horizontal photographs, get really close to your subject. It is okay to chop off the top of their head (but try not to chop off their chin). Experiment with different compositions and framings. Sometimes when you’re shooting a horizontal photograph, you can just photograph their arms or body language.

When you’re shooting vertical photos, try to experiment with uncommon compositions. Put their eyes all the way on the bottom of the frame, or on the top of the frame. Switch things up, and don’t just make a typical head-on shot (although this sometimes is the best image).

But the take-away is this: if you make a lot of variations of a person (horizontals, verticals, close, far-away), you have more freedom in the editing (selecting) process to choose what you think is the best image. It is always better to have more choices and “optionality”.

13. Shoot from different perspectives

Not all the street portraits you shoot need to be shot head-on. Try different perspectives. Shoot from the left, shoot from the right, try crouching down really low, and try to tippy-toe.

When working different perspectives, you can also direct your subject by changing their gaze in different directions as well (looking up, down, left, right, etc.).

You never know which perspective works the best, so once again— try different variations.

14. Get close enough to see the color of their eyes

So how do you know if you are “close enough” when photographing your subject?

I have a simple test: get close enough to your subject where you can see the color of their eyes.

It can be scary and awkward to get close to strangers, and get that sort of intimacy. But I do believe the benefit of being closer to your subjects is this: with physical proximity, comes emotional proximity. This is very similar to the famous Robert Capa quote: “If your photos aren’t good enough, you’re not close enough.”

15. Try to shoot with / without a flash

Another thing when you shoot street portraits: try to experiment using a flash. The flash doesn’t need to be something big, bulky, and distracting— it can be the small-integrated flash you have in your camera. Or if you don’t have an internal flash in your camera, pick up the cheapest, smallest, and most unobtrusive flash.

In terms of technical settings when it comes to shooting street portraits, I generally recommend people to shoot in “P” (program) mode and to choose your ISO to 800. And if you shoot with your flash on “P” mode, you don’t have to think too much about the technical settings— your camera will figure out the exposure for you.

The benefit of shooting with a flash with street portraits is that it adds more contrast to the subject, and gives them a little “fill flash” to light up the shadows in their faces. Not only that, but the benefit is that it helps separate them from the background.

So when you’re shooting street portraits, try to shoot both. Try to get photos of them with and without a flash. You never know which will work better (natural light or artificial light)- so try to do both.

16. Capture hand gestures (get their hands close to their face)

Another practical tip when it comes to street portraits is this: try to capture hand gestures in your subjects (preferably close to their face).

One of the most boring ways to shoot a street portrait is to have someone’s hands idly by their sides, and looking straight at you. Often getting interesting hand gestures makes the photograph more energetic, alive, and animated.

Simple suggestions: you can comment on something close to someone’s face to get an interesting hand gesture. For example, you can comment on someone’s cool glasses or sunglasses, and ask them where they bought it. And when you ask them that, most people end up taking off their glasses (which makes an interesting hand gesture).

Another example: you can compliment someone’s hair, and ask them how long they grew it or where they got it styled. Then naturally your subject will start playing with their hair, which also makes an interesting hand gesture.

Sometimes you can be a more direct by asking them to just put their hand on their chin, and ask them to think contemplative thoughts. Or if you’re talking to them and you see them do an interesting hand gesture (like wiping their nose), you can ask them, “Oh, can you do that again? Can you just wipe your nose again?” and ask them to “replay” their hand gesture.

17. Take a step back

I know that I mentioned the importance of physical proximity to your subjects, but there are certain situations where taking a step back is actually beneficial.

I think in street portraits what you want to do is avoid the awkward “middle distance”. Meaning— you either want to be really close to your subject, or intentionally far from your subject (to capture more of their surroundings).

The best way to get a strong portrait from a distance is to try to capture an “environmental portrait” — where the background of your subject is as interesting as your subject. You try to give your viewers a “sense of place” in your photograph.

For example, in this photograph of a man I shot in San Diego, I loved his outfit, but also loved the hobby lobby in which he was sitting in. Instead of intentionally getting really close, I took a step back to get the entire environment. After taking a few photographs, I approached and asked him: “So what you up to?” He told me: “I own this hotel!” I was amazed, he invited me to the VIP clubroom to hang out (but I had to politely decline, as I was on the way to teaching a workshop).

So when shooting environmental portraits, ask yourself: is this background adding to my image, or distracting from my image? Incorporate interesting details into your background which you think your viewer will enjoy.

18. Work the scene

I wish I talked more about this earlier on, but when it comes to shooting street portraits, don’t just take one photograph and move on. Rather, work the scene. Take many different photographs and different variations.

I know the gut-reaction is to take one photograph really quickly, and then wanting to run away.

But rather stick with your subject. Take many different photographs of them from different angles, positions, and distances.

Whenever I see a subject I am really interested in, I will try to take as many photographs a humanly possible.

In one image I shot of a man with a face tattoo in SF, I shot 50+ photographs of him all from different angles, exposures, and backgrounds. This gave me a lot more freedom in the editing phase to choose the image that I thought was strongest.

A simple rule is this: when in doubt, take more photographs.

19. Realize a street portrait is more about yourself, not your subject

An interesting lesson I got when watching a documentary of Richard Avedon was this: he told the interviewer that his portraits were less about his subjects, and more of self-portrait of himself.

I think we should take the same approach and thoughts to our portrait making.

In terms of “ethics” of shooting a street portrait, is it “ethical” to make a photograph of someone in an unflattering way, or in a way that perhaps “distorts” who they are in “reality?”

For me, I think if you take the line of thought that street portraits are more of a self-portrait of yourself (rather than a realistic depiction of your subject), you are in the clear.

Because for me, I generally try to look for the sad, melancholy, and depressive aspects in people. I generally shy away from “happy photographs” of people smiling, because I think even though I am an optimist at heart, I can see a lot of pain and suffering that people in society experience. I want my photographs to highlight that, and to feel more emotional.

But ethics is a tricky issue. Philosophers have been debating the ethics of everything for millennia. My rule of thumb is this: treat others how you would like to be treated. And not only that, photograph others how you would like to be photographed.

Personally, I don’t mind having my photograph taken and “distorted” by other photographers. I know that how my photograph is less about how I look in reality, and more about what the photographer wants me to look like.

I am also very comfortable being photographed, so I don’t mind if people move me around, or take my time. In-fact, I love the attention.

But that is just me, and you might be different.

So ultimately shoot street portraits in a way that feels authentic, genuine, and real to you. And when in doubt, follow your heart and your gut. Don’t let others dictate your rule of ethics for you.

Assignment #5: Become comfortable on the other side of the camera

One of the biggest barriers that prevent street photographers to being more comfortable in the streets (and shooting street portraits) is that they themselves don’t like having their own photographs taken.

If you don’t like having your photograph taken, that’s a serious problem and barrier. How can you expect to take portraits of others, if you don’t like it being done onto you?

Another issue of not being comfortable of having your own photograph taken is this: you assume everyone else doesn’t like having his or her portrait taken. But in reality, that isn’t true. There are some camera-whores out there (like me) who love attention and love being photographed.

So this exercise can hopefully help you feel more comfortable on the other side of the lens.

The next time you’re out on the streets and you find someone interesting you want to photograph, start off by asking if they can take a portrait of you. Hand over your camera to them, and ask them to take 5 portraits of you in different angles and perspectives (needless to say, don’t hand over an expensive camera to someone who you think will run off with your camera).

Then once they’ve taken a bunch of photographs of you, then ask if you can take their portrait. This makes the image-making process a two-way street, and makes it a reciprocal process.

And while you’re having your own photograph taken, ask yourself: “What makes me feel uncomfortable?” And based on that, you can change your approach in terms of how you like to approach strangers and shoot street portraits.

Another idea: try shooting more self-portraits of yourself, and build up your own inner-confidence. Shoot selfies of yourself in the mirror, in puddles, in reflections, and just shadows of yourself. Perhaps put your camera on a tripod, use off-camera flashes, whatever. Give your camera to your friend or significant other, and direct them to take an interesting photograph of you, and practical feeling more comfortable being photographed.

You will never be able to have true confidence and comfort shooting street portraits of others, if you yourself don’t like being photographed.

Conclusion

I hope this e-book has helped give you some ideas, tips, guidelines, or inspiration to shooting street portraits.

Ultimately if I can sum up the entire book in a sentence it would be this: the more vulnerable you make yourself to your subject, the more vulnerable your subject will be to you. Treat others how you would like to be treated, and do it in an open, authentic, and loving way. Have empathy for your subjects. Don’t think that the image is everything, sometimes the interaction you have with your subjects is more important than the photograph itself.

Don’t be afraid. Don’t hesitate. Don’t think you are pissing off or upsetting people.

You are trying to uncover a deeper part of someone’s soul. You are trying to find this hidden beauty, or this hidden pain. But you are doing it for all the right reasons.

Shooting street portraits is damn scary and nerve wrecking. I think asking for permission to photograph a stranger is actually much more difficult than shooting candidly. Because you have to make yourself vulnerable to being rejected.

But know the more you get rejected, the more resilience you will build up— and soon you will love to get rejected (or become indifferent to it). Because the more you get rejected, the more you are to have someone say “yes”.

So if you’ve enjoyed this book, email it to a friend, share it on Facebook, tweet it, or better yet— use the lessons and assignments in this book in real life. A book is useless without making action.

So go out, ask for permission, expect rejection, but try to get a few “yes’s”. Interact with strangers, step out of your comfort zone, and make beautiful images that are genuine, have soul, and full of heart-throbbing emotion.

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Open-source

This book is “open source”— meaning you are more than free to do anything you want with it. You can change the text, translate it into a different language, or copy-and-paste passages or ideas to your own blog.

So I recommend sharing it with a friend, or thinking how you can help edit or make this even better by remixing it.

Share the love and pay it forward! Enjoy! :)