Photography is magic. It gives you the ability to freeze time, forever. And for me, the most magical genre of photography is capturing the drama of the street. It's spontaneous and unrehearsed, accessible to all and the most challenging type of photography in a world mostly out of our control. Street photographers organize chaos within the frame and hope to capture an insightful moment that communicates a truth.
The term "street photography" is really just a label that's open to interpretation. For me, shooting in the street is personal, and the more personal you make your work, the more universal it becomes.
My preference is to capture candid street pictures with people in them, but I also shoot road signs, billboards, storefronts, architectural details, and quirky moments in time. I want to show everyday beauty, characters, moments, places, and details viewers may otherwise miss.

Waiting for a bus in Lisbon, Portugal.
Only you can define what you want to say and show in your images, but whatever it is, you need to be able to react quickly. Because in the perfect storm that is street photography, if you hesitate, you miss the picture.
TECHNICAL TIPS
If you’re new to street photography, start with the camera you have. Phone cameras are the least obtrusive, DSLR cameras have the widest variety of options, and in-between are mirrorless and point-and-shoot cameras. The important thing is to learn your gear inside and out so you don’t have to think, only react to the moment in front of you.
Once I commit to my gear (usually one DSLR camera and one lens), I take advantage of what it has to offer. For example, I reduce the chances of blur from camera or subject movement by setting a fast-enough minimum shutter speed, such as 1/400th of a second, sometimes in conjunction with auto ISO. (Unintended blur is the most common technical issue with street photography.) You don't have those options when shooting with a phone camera, but you can press down and take a burst of images to increase your odds of capturing the right moment.

A Lisbon cafe. I work fast, and people often don’t realize I’ve taken their picture, even though I'm using a big DSLR.
Editing. After you've captured an image, it's time for post-processing. I have a minimalist philosophy: a stripped-down shooting system, simple compositions. And when it comes to post-processing, I want to maximize my results with a minimum amount of time in front of the computer.
I use Adobe Lightroom Classic for digital asset management and image editing. Adobe Lightroom CC is another management and editing option, with a different interface than Classic. You may want to check out both to see which you prefer. Or, if you're already comfortable editing in Adobe Photoshop CC, you'll find the tools I describe below in Photoshop's Camera Raw filter.
My Lightroom Classic workflow is straightforward. I keyword, cull, and organize images in the Library module, then process my final selects in the Develop module.
I always shoot in RAW to preserve the highest image quality and dynamic range, and I begin processing by applying minimal initial adjustments to color and contrast to compensate for the unprocessed RAW capture. Typically, I start with the Basic panel and work my way down, making global adjustments, such as white balance, exposure, and bringing back highlights and recovering shadows. I like the punch of extra clarity. Sometimes I hit the Auto button for a starting point and adjust sliders from there.

I love to shoot this kind of urban landscape even when there are no people in the scene. The color of the curtain drew me to the scene.
I then make targeted adjustments using the HSL panel, adjustments brush, and radial filter to further draw attention to important areas in the image. Range masking and auto masking for the adjustment brush and the target adjustment tool make quick work of isolating the areas to adjust.
I love black and white photos, and Lightroom gives me amazing precision with the Black & White Mix sliders, letting me play with very specific underlying tones when enhancing my black and whites.
If I can make a picture better through cropping, I do. I maintain the original aspect ratio, create a crop box, and move the image around, finessing the crop to maximize the impact of the composition. For me, it’s important that all of my images are the same shape to give my work a consistency.
Lightroom tracks my ever-growing body of work and lets me explore new narrative themes by creating collections and collection sets, where I can experiment with image sequences and threads that might morph into new projects. I also use it to mock-up books and create slideshows, and when I sell a print, I output directly from Lightroom.
BEYOND THE TECHNICAL
The technical aspects are easy. The concepts that are tougher but vital to success as a street photographer are patience, shooting a lot of frames, and leaving your comfort zone—that's the most difficult for many people, but also what makes street photography so satisfying and rewarding.

This is the kind of quirky photo I love to find and take.
You can choose to engage people in the scene, or you can be a fly on the wall. I often try to blend into the background to capture authentic story-telling scenes without influencing them. I tend to use wider lenses—my favorite street lens is the 35mm focal length on a full-frame sensor camera. This puts me physically closer to the scene, communicating an intimacy. With close proximity, I sometimes get noticed and occasionally people question why I'm photographing them.
The image below of a mother and son looks relatively serene, a quiet moment captured on a Montreal bus when I was a teenager. But raising my camera to my eye and clicking the shutter felt very different from the calm the photograph depicts. It felt more like a bungee jump because when the shutter sounds, anything can happen (which is why cameras with silent shutters can be so beneficial).
[Vertical image] Mother and child on a Montreal bus. It's a simple image but not an easy one to take on a crowded, quiet city bus. Street photography is not a time for timidity; be bold even if it’s outside your comfort zone.
[Horizontal image] What seems like a scene from West Side Story was a chance encounter. When I street shoot, I flip a switch and I’m “on,” looking for images I may not normally notice.
On those very rare occasions when things go sour after the shutter is clicked, I do what I can to diffuse the situation. Sometimes I engage; often I try to avoid the confrontation by distraction, pretending to ignore the person and aiming my camera at something else.

I noticed how the light would illuminate people walking by the entrance way, so I waited while others passed. I was “lucky” the girl turned toward the light; I use quotation marks because luck favors the prepared.
I make no apologies. Street photography is a historical record. I capture the world at a specific time and place for posterity, and I'm not out to exploit or take advantage of people. It's legal in most places to photograph someone without their permission because the expectation of privacy is different when you’re in a public place. In most countries, you can even lawfully post and print and sell that image as long as it’s for personal artistic expression and not for commercial advertising.

If I’m not asking people for permission to photograph them, I capture life as I find it, without interruption. It's better to beg forgiveness than to ask permission, but when a person doesn't want their photo taken and I can’t convince them otherwise, I comply.
All that said, when someone doesn't want their picture taken, I may try to change their mind, but I always respect and honor their ultimate wishes. If a situation escalates into a problem where deleting the photo can help, then I delete it, but that's happened only once.
Enough negativity. I’m confident your street experiences, like mine, will be overwhelmingly positive. You'll learn to love risks because they so often lead to strong images.
Getting out of your comfort zone in street photography also means boldly exploring interesting angles: low, high, and close to my subjects.
There wasn't much time to grab these streetcar images. I don’t hesitate or think, I act. I used black and white as a way to eliminate distracting color and cut to the content and message of the street image.
I then got into the streetcar and out of my comfort zone, as I did as a kid on a Montreal bus, to make these two images.
Let's talk about those times when you do engage people on the street. It may not be natural to approach strangers, but it gets easier, and it’s worth the risk and effort. I've collected many positive experiences from talking to strangers, and some great images, too. I liken the process to jumping into a cold lake: at first it’s cold and uncomfortable, but eventually the water feels just fine.
I rarely use the phrase, “May I take your picture?" The subject often expects me to shoot only one frame, but I want to work the image. Instead, I go up to people and ask, “May I talk with you for a moment?” I then deliver an elevator pitch as to why I want to photograph them, and they end up more flattered than skeptical. That gives me time to shoot a variety of images while moving around, adjusting the framing and the lens-to-subject distances. However, I do get rejected sometimes, and I don’t take it personally. How can I? They don’t even know me.

This young woman posed for me. In the brief session, I tried a variety of different things, asking her to look at me and away.
The more I learn about a person from our brief exchange, the more likely that I'll say something that will provoke a compelling expression. (The eyes are often key, since they can communicate so much.) My instinct lets me know if I should get personal, asking about their proudest moment or secret dream. I also try to find the best light, or if the light's not there, I supplement it with a small flash and diffuser. Often the best images come in the last few frames, so the more time I can squeeze out of a situation, the better the images become.
I'm not a patient person, but I know that patience is rewarded in photography. It's why I search for scenes and situations with visual potential, and then wait for the elements in the frame to come together. Try parking yourself at a busy street corner; let the imagery come to you as you wait, eye to the viewfinder, triggering on impulse. You may choose to focus on one plane within the photo and let serendipity create visual layers for complex street compositions.

In this image, I framed the scene and focused on the person illuminated with the blue light. By staying in one place and shooting a variety of pictures, eventually I was able to make a layered image that I liked.
Photography is a numbers game: The more you shoot, the "luckier" you get. Press that shutter a little more than you normally would. Capturing that one, fleeting, decisive moment is not easy. Most of your attempts won't be successful—and that's OK. There will be a time when planets align and all the moving parts come together to create a strong street image. That’s the magic. That’s street photography.
April 27, 2018
All images ©Steve Simon