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Street Photography: The Art of Photographing Strangers

Lesson 7 of 20

How To Tell Your Story Through Photos

Ashley Gilbertson

Street Photography: The Art of Photographing Strangers

Ashley Gilbertson

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Lesson Info

7. How To Tell Your Story Through Photos
Some stories try to change the world, others just celebrate the beauty and fun of it. Dig into researching the location, narratives, and existing work on a potential story. Learn how to build and pitch a photo essay, including a sample pitch.

Lesson Info

How To Tell Your Story Through Photos

So I've been talking a lot about the's like big issues that often pretty hard teo manage I think so I wanted to remember that doesn't always have to be like save the world that's fight injustice on dh you know be that photo journalist but I guess I am except I you know I feel like I'm central casting sometimes for like theo bleeding heart photojournalist I am and it's true I am but I also thought about stuff that eh like just think is amazingly good fun sometimes and I do this to try to balance myself out like I get so deeply invested psychologically into the stories that I'm working on that I need thio almost come up for air and remind myself that sometimes it could just be whimsy on dh great fun so one of the things that I've been doing over the course of last year's photographing black messengers in new york uh that's because they have their own society that have their own language they had their own cliques they they're not welcoming teo outside of so much so but I love that I coul...

d something I very much identify with you know is thie is ah I think at heart and introvert on dh you know somebody who likes to have a very tight small group of friends I really relate to these guys they also have a very healthy disrespect of the law which I which I family respect um so this is one of the bike messengers, cooper ray, that I photographed, he climbed up on top of a building. Teo, look at the downtown area of new york from up there, which he just does regularly he's great. So not all stories have to be, you know, as driven or is focused on trying to change the world, sometimes you can just celebrate the world as it is and that's beautiful in itself. Yeah, when you do stories like this, when you focus on things like this, like you were mentioning before about just focusing on your own backyard and being able to make that work for you, how do you get funding for these projects, or how do you market this? I don't this stuff I'm not marketing, like I showed the work in a cafe just fun in new york, except like, I don't really put on social media, and this is like, this goes back to when the questions we're asking earlier, like a lot of these guys, you know, like the messengers and photographing, like, what do you do with the pictures? You know, like, maybe I'll create a little magazine, maybe I'll do a book, maybe put him in a magazine, except like, I'm gonna be shooting it for a few years. So to say, I don't know like I'm going to be around, I'll tell you when something happens, but for now, I don't know, and as far as funding goes, I intentionally choose stories that I can shoot on a low budget, so like this, all you need is a bike. Um, so I tried to find things that I'm not going to eat up, you know, that they'll they'll it'll be an investment of time, but it won't be a huge investment of resources, they don't need translators, I, um, you know, in order to gain entry and it's still like, this is a fun story that I'm enjoying doing that it's still a closed society, so you still need to find a way, you know, to get into this. So in order to photograph this, um, I became aware of a guy who was a black messenger guy come christopher lee, um, and chris had been photographing, like, making a documentary about the bike messengers and the cycling community in new york city, you know, from the perspective of the messages, so I met with chris to say, like, I'd like to photograph the guys that you're photographing but don't want to step on your toes, you're like, this is his scene. This is his thing, and I'm coming into it on dh, you know, I think it's it's a sign of respect like this is your scene, do you mind if I do you mind if I work in this as well? Um, the funny thing that though, was I wanted to get into the vaccine and chris said, yeah, I'm of course I'll make all the introductions that you need, but I also want to get out of the vaccine, so can you help me with photojournalism? So we've sent he since became my apprentice and so high I'm sorry. One more question, how much time do you spend you live in new york? I assume? How much time do you actually spend in new york vs out on assignment and other places out of the year? I don't know, I will say that I just had a conversation a lot this morning discussing how to talk about how much I travel with my six year old like it's more than it's a lot, uh, it's less than half for the time usually, um so on a busy year, it's, maybe half sometimes, but I try to keep it down to like thirty or forty percent, but I never look at the numbers because I'm scared of what they're gonna show, um I mean, I try I try really hard to work in new york and like, this is the thing, like when you're in your twenties in your early thirties, you know, you could be jumping on planes and going all over the place, and it doesn't affect your well, it does affect your family, of course, except it doesn't affect your kids or your wife so much because he just going around you like jack kerouac with camera, it doesn't really matter, but when you start having a family like you have to start really choosing your trips, you know, and at this point, like I want to say, this is cool story and the philippines that I think I might go over and have a look at, you know, like I find stories that I know we're going to work, I find stories that I research and set up contacts for, like, I can't waste two weeks of my life now I have too many responsibilities. Do you ever reconsider a story based on safety? Yeah, of course. Yeah. I used to do a lot more of the unsafe stuff. But now it's it's, you know, there's there's less chance of dying involved, um so as far as like once you've identified an issue or or even a space for that matter could be zuccotti park where there's occupy wall street people or it could be the park in chicago, you know, it could be a neighborhood of your city, you should try to research that area, find out aspects of it that could be surprising or interesting find out look for not just other photographs of these places that eggs just like radio is actually a great place to find stuff and now that's all archived online the way that radio reporters actually described these situations they're looking at a kind of great for photography because you get to imagine how it might be without looking at somebody else picture of being influenced by it, you're gonna go out and copy a radio reporters picture so it's it's, one of the mediums of research that I love I love using um so television and newspapers making sure that you can add a fresh voice to the story, like I said with the banlieue piece it's pretty red this happens because almost always a fresh way to approach a story, but the banlieue piece was just so good, I I couldn't there's no way I'm going to come close to it, so I left that one but usually looking at the other approaches that have already been made it gives you the opportunity to think a little more freely as as what you could do that's very different well slightly different you know, like in the case of the refugees that was slightly different I felt that the media media I'm a part of media but my colleagues in the media hadn't been presenting the story in a fashion that best represented the you know, the emotional bread that that story that they were in fact a lot of refugees that we're that we're making this journey that there were moments of relief a moments of joy, moments of uh great compassion and empathy and camaraderie and I wasn't seeing a lot of that in the press I was seeing a lot of the drama on, you know, like the the crying refugees on the beaches and that was that's one note of a multi faceted story so I went the intentionally trying to fill out the different emotional breadth of that story you know, that's not that different it's a little bit different but it was enough you know, people really engaged with that work um when you can't find a lot of work when you find something really obscure which happens um or something that's really new which happens a lot in technology there's not a lot of people shooting technology it's not easy to shoot um if you can't find work that exists, then I go on instagram because everything exists on instagram he's going to search the right hashtags as you'll see in the next slide andi stop making contacts as I said on this story we did about hacker hostiles hacker hostel to these places that they offered cheap accommodations well, cheap accommodation doesn't really exist and it's an oxymoron in san francisco right? But cheaper accommodations for people who are in the tech industry or movement as they like to call it so they cram you know dozens attends of people into one small apartment complex or former hotel on giving cheap rent and everybody sort of feeds off one another as faras context goes, it goes what silicon valley and have you seen that show that like the silicon valley had like I think what's his bachmann's house he's kind of a mini hostel except like they'll get their own room like what you often see is like a lot of bunks crammed into one room or like I was I found out about this one place in the course of my research so there was a story in the new york times um piques my interest about this story and I found out there was another place another hostel called twenty mission which is on the corner twentieth admission in san francisco and it's a full mccracken hostile it was this like run down place that all these crackheads used to go in and usedto smoke um it turns out on entrepreneur came in on dh that bought this space on built it out piece by piece and like filled it up with uh with tech people and it turned into this like totally amazing space but I couldn't find any pictures of it so I went on instagram on star search like twenty mission hashtags and so then I start getting a visual sense of what the place looks like obviously they have pretty good parties that's what the kitchen looks like in there eating you know, as a group they got like, this weird internal space in a new roof space and then they have like this guy whoever he is like coming in with like, wearing he looks like six million dollar man is something I know so I have some sense of visually what this place is going to look like. So from that I'll write a pitch the pitch like this is a pitch that I sent to an editor and it's in the pitch kit um I called her hacker hostels uh I think that the story ended up calling it hotel startup but um so I said outside of the hbo series silicon valley visual representation of the tech industry a rare beyond the high flyers with no idea who populates and work it's within the scene or what it looks like my shooting a photo essay on a hacker hostel readers will get a sense of mohr of more common players in the industry, the ones who don't sell their startups millions of dollars. So I go into generally an editor's going to be the first paragraph on decide then and there if they're gonna buy the story or not. But for my purposes, I'd like to believe that sometimes they read the whole thing. I'm going to talk about what these places actually look like. Forty and sixty people living in a dorm, predominately young men, um, they share their dreams of quick wealth and prestige. People stay for two weeks to a few months. It's, similar to the incubation style of spaces or elaborate a ivy league university. Um, they have pitch patties on monday. Um, like designed throughout the hostile networking at all hours communal kitchens. Um and that nobody had bean into these places and lived in this place. So, um, I found this place. So this is twenty mission. So this is a guy called madonnas. So I went in the eye was everybody was a stranger. Like I thought it was totally bizarre. Like think it never gets old man like you never get used to it, it's always really uncomfortable. Like I turned up on a sunday night at the hostel. I got off my jetblue flight like driving got a cabinet. San francisco got over twenty that mission. I don't know how to get in. So I like I found a door with this graffiti all over it, like banged on it. Somebody comes downstairs and he's like yeah, come up. I go into the kitchen with all my stuff. It was like, all right, see you, where's, my welcoming party like there's? No way. I'm not expecting a red carpet, but thanks for finally somebody comes in he's like a either journalists. Yeah, like years. Your room and I get some room that was like, yeah, it was it was weird. I mean, it's, I was really uncomfortable, but so were they likewise there general is coming to live amongst us. Um, you just write everything yourself I normally take. I take extensive notes at the end of every day, I sit down my right. I mean, I'm normally writing anyway, and I think, um, like in the creative industry will find a lot of a lot of people carry on, no paddle the time, always scribbling down ideas and the ideas may go, most of the ideas will go absolutely nowhere. Um so just we're sitting and writing ideas for proposals and pitches like you should be going through that keeping nose thing going through every couple of weeks and looking at what's stuck what's still a good idea and then on stories like this I sit down I am taking notes throughout the day I transfer that to a computer file and then I'm taking like diary like long diary entries from each day I'm writing down quite says I hear them um this is obviously a little light situation do you also traveled with lights isn't kind of know how to shoot with light. Okay, um, so eventually I started meeting people like I just sat in the kitchen like a freak on waiting for people to come in and I would introduce myself and so the first day was pretty weird and then the second day was a little bit better and then the third date was a little bit better and then by the fourth day like people, you always that guy I'm ash and I'm taking pictures and I'm a generalist, so I ended up gravitating towards darkness who's the guy on the computer here who's finishing coating some software that he was writing while his friend is sucking up a whippet and his other friend having the beginning of an orgy on the bed behind them um and it was it was cool like the story itself was really interesting they were totally open to me like they knew what I was doing and there was never any question as to what I was doing that you know, it was always clearly established that I was a journalist which is important, especially in your building trust they could be too much trust at a time like this things that maybe they don't want to be photographed, so I'm often holding up my camera saying don't forget that I'm a journalist um so then from the notes that I wrote like the bloomberg businessweek, we wrote a story from that put together like they have a have a tv studio that goes straight to youtube on in the basement have got a garden at the top um in the bottom right picture um one of my favorites the they had a girl come over for the night on dh like they were totally stocked like this is pretty cool like trying to entertain her with music and playing in town and stuff like that. Then a bunch of guys came into the room and noticed that this kid sitting on the couch was wearing an apple watch and like they will completely ignored the girl they're like oh my god, is that the new apple watch say I remembered where I wass um that's all see on the right who's drinking that uh soylent which is a meal replacement drink up on the top left this was thiss was in question of so whether or not I would actually get to photograph this or not but that was the initiation ceremony that people would have to go through when they joined the hacker hostel um you know dennis is bed lab I guess um it was pretty funny they swore that they had to clean up after themselves and dry off before they got out of the shallow it's all communal showers and bathrooms and the mets yoga on the roof and you know, I'm still even though I was there for ten days and even though I'm still shooting every day and everybody knows what I'm doing before each situation I'm still asking permission if people mind if I shoot you know, like they're doing yoga on the roof and like everybody's comfortable with me they're all cool with may but still they're doing your guy go on before it begins I said, do you mind if I take some photographs of you doing yoga on the man in this picture is like actually I do think I'm trying to do yoga it's not going to be very cool having some guy like running around taking my picture so is there a way that you could do this where you stand back a little bit and just do it for the first few minutes yeah that's cool that's all I need to not overstayed your welcome it's sometimes important um and I think that would lead into, like, not overstaying her welcome with leading to your question of when do you actually finish the story often there's like a hard deadline that you have to respect the magazine deadline you got a file on a certain date, but then I usually set limits on a story going into it like the iraq story. There was no outpoint, there was no way to end it. It just it happened in that case. Naturally, I couldn't go back anymore. I burnt myself out. I didn't know how to keep I don't know how to keep shooting what felt like the same thing. I didn't feel like I was adding to any sort of constructive conversation anymore. I felt like I needed a new way to address this story, which is why I started looking at veteran's issues in the united states and in the bedrooms book um on the bedrooms book, you know that that could have been a book that's forty bedrooms in that book, it could have been a book that went on for I was going to say years, but it did it could have been a book that never ended, you know, when do you actually what parameters do you set to prevent yourself from working on that for the rest of your life and maybe maybe you do wanna working the rest your life, but I had to set really hard parameters that I'm going to do veterans of the iraq and afghan wars on because if I start doing veterans, I found that there was a bedroom in charlottesville that belonged to a vietnam vet that have been there for forty years if I photograph that they want to go earlier one a photograph the room that's in france that's the world will one veteran's room um and then I'm going to go that deep that wanted expand this memorial project into cancer victims into ka crash victims and then when does it stop? You know, you have to have your self imposed deadlines on dh limits on the type of work that you're trying to do and where it will stop otherwise it's too big, you know, this is the importance of photographing things in a local perspective photographing specific families you will organically come to an end except self imposed deadlines like how does this work look after a month? How does it look after three months and that's a long story, you know, on a think on photographing strangers on the street, you know, photographing the same street corner can be great the same place every day for a week you know, you start recognizing characters. You start recognizing people who coming back. The people who said no last week might say yes next week. But then when do you stop working in that one corner, you know, but I think, naturally that happens, and if it doesn't happen, then so what? Like, you shoot the same street corner of fifty years? It would be an amazing project, I think.

Class Description


  • Confidently approach strangers for street photography
  • Refine your eye for strong compositions
  • Choose the right gear for street photography
  • Tell a story through street photography
  • Write captions to accompany your work
  • Cull and edit your street photography images
  • Use street photography tips for building a career


Find the courage and skill to photograph strangers in public. Work with renowned street photographer Ashley Gilbertson to build both the confidence and skills necessary to succeed as a street photographer. Learn how to capture people moving through everyday life in artistic ways. Find out how to approach people in the street -- and how to photography anonymously in public places when everyone says no.

From understanding gear and the nuances of focal length to working as a documentary photographer in a public space, take your passion for street photography to the next level. This class isn't for beginners learning shutter speed and aperture for the first time -- it's for anyone that's ever wanted to work in street photography but struggles to build the courage to do so.

Watch behind-the-scenes videos following a real street photographer in action. Hear tales -- and see sample images -- of street photography across the United States and abroad, including major cities like New York and Chicago. Build captions and edit images with Photomechanic and Adobe Lightroom Live. Dive into an art form that reveals the complexity of human nature with Street Photography: The Art of Photographing Strangers.


  • Intermediate photographers eager to try the street photography genre
  • Enthusiast photographers branching into documentary style photography
  • Advanced photographers struggling to come out of their shell to approach strangers

SOFTWARE USED: Adobe Lightroom 6.0


Australia born photographer Ashley Gilbertson is a well-respected documentary style artist that many consider among the best street photographers. From working on editorial shoots to personal projects, his work has earned him an Emmy nomination, the Robert Capa Gold Medal, and an American Society of Magazine Editors Ellie award. The street photographer is also the author of two photography books and a regular writer for publications like The New York Times and The Washington Post. Based in New York City, Ashley's work has been featured in major publications as well as museum and art galleries around the world. 



I have taken more than a few of the Creative Live courses. I have, in general, found all of them to be very good and I have learned something important from them all. Not always enough of exactly what I was looking for, but something useful and important. This course was absolutely amazing. The best I have taken. I would like to download it and see it again and again. Ashley's style was authentic, humble, yet confidence inspiring. The information he gave was focused and totally useful. He shared both philosophy and thinking as well as real tools to learn - whether they be soft stuff (like how to approach someone) or hard stuff (like gear and settings and such). I cannot recommend this class highly enough. If you want to learn to do "humanistic photography" (his term which resonated with me), this is best I have ever taken!


This was a terrific and wonderful class. Ash was superb. His stories were awe inspiring, his passion was evident and his ability to teach was flawless. I would take any other class by him and actually can't wait for more of the VII agency programs eminating from Ron's class during photo week 2015. A great great addition to Creative Live's orbit.


Wow, I loved this course - I watched the whole thing, and most of it twice, during the first run. Ash is is intriguing, a good teacher, honest. I found this class to be so inspirational. I especially loved his encouragement about talking to strangers, asking to take their picture- "what's the worst thing that could happen?" And the videos watching him in action were motivating- you saw him make connections but also saw him get rejected too, but he keeps such a positive outlook. Love this class, please more photojournalism!