How to Overcome Obstacles in Street Photography

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Manila, 2013

I just finished a new book: “The Obstacle is the Way” by Ryan Holiday. The book is a huge source of inspiration for overcoming challenges– and using them to your advantage. In-fact, Ryan uses the quote from Marcus Aurelius for the title of his book: “The obstacle is the way” meaning that if it weren’t for obstacles in our life, we wouldn’t grow, develop, and mature.

I thought a lot about the obstacles I’ve faced in street photography– and how I have used those negative experiences and turned them into positive ones. Here are some thoughts on how you can continue to grow and develop in your street photography– and utilize negative experiences to your benefit.

1. See the opportunity in every negative experience

Manila, 2013

a) Negative experiences shooting in the streets

One of the biggest setbacks I have is when I’m shooting in the streets and I have a negative experience. For example, I remember when I first got yelled at, cussed at, and threatened by people on the streets by taking their photograph.

At first, these negative experiences lead me to not want to take more photos in the streets. However over time, I realized that these negative experiences were really important. Why? After the negative reactions I got in the streets– I realized that they weren’t all so bad.

Who cares if someone yells at me in the streets and calls me a creep? Like the saying goes: “Sticks and stones may break my bones, but words can never hurt me.” Sure it feels crappy to have someone yell and scream at you, but the confrontations I get in the street are rarely physical.

Also these negative reactions I got in the streets helped build my courage. I realized that getting yelled at in the streets wasn’t that big of a deal. I would generally quickly apologize, and move on. Over time, I have built up a resistance to negative feedback in the streets– meaning when people yell at me now, rarely does my heartbeat go up (as it used to).

b) Losing all your photos

Helen Levitt, NYC, 1972
Helen Levitt, NYC, 1972

Another negative experience I’ve had in my life when it came to my photography was having my hard drive crash (and losing around 2 years of photographs). At first I was absolutely devastated– but then again that negative experience ended up being a positive one. I was pissed that I lost all my files, but it gave me a fervor to go out and start creating a new body of work which ended up leading to better photographs.

Helen Levitt had a similar experience. She was commissioned by the Museum of Modern Art to product color street photographs. After a few years in, a burglar broke into her house and stole all her color negatives. Rather than simply giving up, she used that negative experience to fuel her creativity. She went out with even more passion than before, and simply hit the streets and ended up creating superb work which she ended up exhibiting in the MOMA with great acclaim.

c) Negative criticism of your work

Tokyo, 2012
Tokyo, 2012

There are times you might also get negative feedback or criticism on your photography. Trust me, I get this a lot. I’ve been called an asshole, a Bruce Gilden wanna-be, a hack, a poser, and other potty word stuff I don’t need to mention here. Furthermore, my work has been called derivative, boring, uninteresting, crappy, shit, etc.

At first, I let all these negative feedback get to me. It seriously challenged whether I wanted to continue in photography. Were what others saying really true? Was I really a poser and a hack? Should I give up street photography all-together?

I then realized that there was no need for me to be so defensive. I realized that I could never please 100% of people with my photography or my work (or even my personality as a human being). That was the reality of life. Although I had lots of people criticizing and throwing stones at me, I still had a lot of people who supported me and gained inspiration from my work.

So from that point forward, I realized that I didn’t want to work hard to please my critics. Rather, I would first aim to please myself– and also please those who actually liked my work.

Furthermore, I have found that the more criticism my work gets– generally the more interesting it is. I think my work that never gets criticized (including articles or videos for the blog) are generally uninteresting.

There is a saying from internet marketer Seth Godin that goes something like, “Nowadays you have two choices: to be ignored or to be judged. You can only choose one.” It is a tough choice– but I choose to be judged.

d) Missing “the decisive moment”

Paris, 2011
Paris, 2011

Another huge source of frustration that I get in my work is missing “the decisive moment.” I have missed this moment from situations in which I didn’t have my camera with me, I had my camera with me but couldn’t get it out quickly enough, or I shot the photograph but the settings were totally screwed up and I didn’t end up getting the shot.

I have also had other experiences in which I wanted to take a photograph of someone, but was too nervous and ended up hesitating (and didn’t take the shot).

I beat myself up a lot over these experiences. I will go to sleep thinking about these shots I “should’ve” taken.

But simply beating myself up for not taking these shots are a waste of time. It is better to learn from these experiences– and make sure I don’t let them happen next time.

So when I miss a “decisive moment” I have learned to always have my camera with me, and always have the settings correctly set to take a photograph.

When it comes to taking photos of strangers (and I feel nervous)– I ask myself: “Will I regret not taking this photograph?” I generally hate living life with regrets, so I risk the chance of a negative confrontation and just end up taking the shot anyways.

Use the power of negative experiences and channel them to help you grow, mature, and build up your skills in street photography.

2. Think differently

Manila, 2013
Manila, 2013

One of the most famous Apple taglines is: “Think different.”

What does “thinking differently” mean in the context of street photography?

1x1.trans Robert Franks The Americans: Timeless Lessons Street Photographers Can Learn

Well, when Robert Frank worked on “The Americans it was a huge departure from what other photographers were doing at the time. Rather than his images being happy, glossy, and clean– Franks’ images were dark, grungy, and depressing. He failed to find a publisher for a very long time for his book, and even when it did finally get published– it got tons of negative press. It was called anti-American, pro-communist, a piece of trash, etc. But now several decades later, it is called one of the best photography books over the last century. By thinking differently and approaching photographing America from a different perspective was Frank able to create a meaningful body of work.

1x1.trans 10 Lessons William Eggleston Has Taught Me About Street Photography
© William Eggleston

Or take William Eggleston for example. He spent the majority of his life shooting in a pretty boring city which is Memphis, Tennessee. He is best known for his color work of capturing the banality of everyday life– through commonly found objects, through colorful ceilings, and urban landscapes.

However Eggleston photographed at a time when color photography wasn’t taken seriously as an artistic medium. All the “real” art photographers shot black and white at the time. So when he had his first show at the MOMA, 99% of the feedback he got was negative. People were horrified to see his color “snapshots” in the MOMA, and lobbied to have the exhibition taken down. Of course fast-forward a few decades, and now he is known as a genius of color photography– and was one of the mavericks who brought color photography into the mainstream photography world.

1x1.trans 10 Lessons William Klein Has Taught Me About Street Photography
© William Klein

William Klein was another badass street photographer who went against the grain in street photography. He too didn’t like the clean aesthetic of Henri Cartier-Bresson in street photography. So he switched it up. He shot with extremely wide-angle lenses at the time (28mm and wider) and would experiment with slow shutter speeds, would cut off limbs of his subjects, and shoot extremely closely to them. He played with his prints in the darkroom, and made them even more blurry, contrasty, and surreal than he captured them. When Klein first published his New York work, it was also hated by many. He went against the grain and thought differently. But his work was able to pave the path for many other edgy street photographers to come– who were more aggressive, liked to interact with their subjects, and who wanted to give a middle-finger to the art world.

1x1.trans 5 Lessons Daido Moriyama Has Taught Me About Street Photography
© Daido Moriyama

The last example of a street photographer who thought differently is Japanese street photographer, Daido Moriyama. At a time in Japan when “serious” photographers were shooting with SLR’s or Leicas– he adopted a cheap and small point-and-shoot camera, the Ricoh GR. Similar to Klein, his work was extremely dark and grungy– with high contrast black and white littered with grain all over. He was also one of the first photographers who paved the way for the “stream-of-consciousness” photography in which he shot randomly and aimlessly in the streets– but would create some sort of loose narrative with his work afterwards. His work also was (and still is) disliked by many. They don’t “get” his work– but he ended up following his own unique artistic vision, and kept with it for many decades.

So even though all these famous street photographers were generally hated and despised for their work early on– they kept “thinking differently” and followed their own unique voice. And over the decades, their work started to gain more traction and respect.

When it comes to your street photography, remember to think differently. Whenever you think differently and go against the grain, know that you will always encounter opposition. But use this opposition you receive to fuel and empower your street photography. Remember once again, aim to first please yourself– then please others.

3. Action, action, action!

Manila, 2013
Manila, 2013

Sometimes in our photography we become bogged down thinking too much, reflecting too much, and not focusing on action.

There is a phrase: “paralysis by analysis” which I try to avoid at all costs. The only way to improve in life is to keep putting forth action and moving forward. In street photography you will approach a lot of obstacles like being unmotivated, not being inspired, and not knowing which direction to go.

However if you focus on action– you will be able to overcome those obstacles. Some actions that come to mind:

a) Shoot, shoot, shoot

The best way to get in street photography is to simply shoot more. There is a saying I read a while back which resonates with me: “To double your success rate, double your failure rate.”

This means, double your failure rate in street photography. Double the amount of bad photos that you make. And the more photos you take, the more great street photography opportunities will come to you.

1x1.trans 10 Things Garry Winogrand Can Teach You About Street Photography
Garry Winogrand, World’s Fair, New York City, 1964

Garry Winogrand is regarded as one of the best street photographers who have ever lived. I think what made him great is how prolific he was. Rumor has it that he would sometimes shoot a whole roll of film just walking down one square block. He passed away with thousands of undeveloped negatives– and some even regard him as the “first digital photographer.” He shot both because he enjoyed it– and he needed to. He only felt fully alive when he was out on the streets, making images.

And of course, the more he shot– the more “lucky” he got. There are theories that if you hand a monkey a camera the monkey will take a good photograph sooner or later from luck. Not to call Winogrand a monkey, but any of us who have any sort of common sense in street photography will eventually make a decent shot if we’re out shooting in the streets enough.

There are lots of moments when I don’t feel inspired in my work. I want inspiration to hit my head like a bolt of lightning. But this is a horrible way to work– because we rarely get those jolts of inspiration.

Rather, whenever I feel uninspired– I just go for a walk with my camera. I don’t have the intention to make a good photograph. I just tell myself: I’m going to go out on a walk, enjoy the fresh air, and exercise my legs a bit. And funny enough– whenever I just get out of my house (and off the computer), I will find that jolt of inspiration from the streets.

If your foot is stuck on gum, you can’t expect to become un-stuck without moving around. The same thing goes with inspiration and creativity.

I feel this is how we should gain inspiration:

Shooting -> Inspiration

Rather than,

Inspiration -> Shooting

Simply by shooting in the streets we will find inspiration. So don’t forget when in doubt– shoot, shoot, shoot!

b) Read, read, read (a lot of photography books)

The best way to become a better street photographer is to educate yourself. Reading art history, the history of photography, and photography art books are all superb ways to become a better photographer (even when you might not be out shooting).

Not all of us can go out 8 hours a day and pound the pavement. For those of us stuck in office jobs, we can still gain a lot of knowledge and wisdom in our downtown. should be bookmarked on your computer. Whenever you are bored, just go to the Magnum website and just browse for an hour or so. Find photographers whose work you like, and you can even see all the photos from their photography books on the site too. Use your free time valuably– and always keep learning.

If you want to find a list of great street photography books, check out my favorite street photography books.

c) Edit, edit, edit

Let’s say you’ve shot a lot, and you read a lot of photography books– don’t forget to edit, edit, edit.

Editing is one of the most difficult things in photography. I personally feel editing is harder than making photographs in the streets.

Editing is time-consuming, physically and mentally exhausting, and the only real way you can express your creative vision as a photographer. The final work that you decide to publish online, in a book, or in print form is what describes you as a photographer.

When it comes to editing, the photographs you decide not to show is more important than the photographs you decide to show. Richard Bram from In-Public once said something like, “The photographer’s most important tool is the wastebasket”. Not to say you have to delete all of your bad photographs– just make sure not to show them publicly.

When it comes to editing, be absolutely brutal with yourself. Only show your best work. For me, I think I get one good shot a month, and one shot that makes me really proud a year. I don’t think we should expect more than that.

Remember– street photography is the most difficult form of photography out there because there is so little you can control. You can’t control what your subjects look like, you can’t control the light, you can’t control the backgrounds. As David Hurn from Magnum says, you can only control where to stand and when to hit the shutter. The only thing you can control 100% is the editing process: which photos to show (and which ones not to show).

4. Focus on the present moment

Manila, 2013
Manila, 2013

In street photography we create a lot of conditionals for ourselves. For example:

  • I will start that photograph project once I have $1000 to travel.
  • I will go out and shoot more street photography once I get vacation time.
  • I will start that photography project once I get a raise at my job and buy that new camera.
  • I will become a better street photographer once I buy that new lens.

However rather than focusing on the future– focus on the present moment. Think what you can do with your photography not later– but now.

I used to think that what was holding me back in street photography was my camera. Sure I knew that “the camera didn’t matter”– but I always felt that getting that new Leica would give me that edge. The Leica would make me more stealthy, more confident, and also force me to carry my camera around me more. Although having a Leica has helped me shoot zone-focusing easier, it hasn’t made me a better street photographer. No camera I have ever bought has made me a better photographer. Only studying photography, shooting more, and being more brutal in editing has made me a better photographer.

So some things you can focus on in the present moment in street photography:

  • Appreciate the camera or gear you own– and go out and shoot with it.
  • Pick up a photography book in your library and analyze it– cover to back. If you don’t own a photography book, go on Amazon and get one shipped to your house. If you are tight on cash, go to the local library and browse some photography books.
  • Go on Flickr or Facebook and offer a critique to another street photographer. Offering more critique will help you better hone your own self-editing skills.
  • Write down a list of photography project ideas. Then choose a project, and set a deadline for when you plan on publishing it.

Regardless of the obstacles you face in your photography: financial, socio-economic, lack of time, or lack of inspiration– know that it is always in your power and ability to still overcome them in the current moment.

5. Focus on what you can control

Manila, 2013
Manila, 2013

In street photography there are lots of things we can’t control. A list of things we can’t control:

  • Whether we get 100+ likes/favorites on social media
  • Whether our photographs get exhibited at the MOMA
  • Whether we get published in a magazine or a prestigious book publisher
  • Whether we get accepted into Magnum
  • Whether we become world-famous and rich off our photography

However there are things we can control in our street photography:

  • Getting out of our house, taking a walk around the block, and taking some photos
  • Offering mentorship, critique, feedback to other aspiring street photographers
  • Self-publishing your own photography book on
  • Pushing your hardest to become the best street photographer you can be
  • Focusing your efforts in street photography and taking it seriously

So in a world with lots of externals we can’t control– we should turn inwards, and just take time and energy with things we can control.

(With 100% certainty) we can’t control whether we will be rich or poor. We can’t control whether other people will like us. We can’t control whether we will be published or not.

So whenever we face frustrations and obstacles in life and our photography– focus on what we can control. Our own will, our emotions, our perspective of the world.


Manila, 2013
Manila, 2013

We will face countless obstacles in street photography and life. We will deal with frustration, “paralysis by analysis”– and things that just get us stuck. We will feel uninspired, unmotivated, and crappy about our photography.

But know that the obstacles in street photography are what make it so exciting and great. Even though it is damn hard to make a great street photograph– once we do, it is immensely rewarding. And why is it so rewarding? Because it was difficult to do.

Anything that is easy to do in life isn’t fun. We need challenges to thrive in our lives.

So don’t set the bar low in your street photography. Set it high. Absurdly high. There is no reason why you can’t become as great as a Magnum photographer. Sure you might not get into Magnum, but you can certain improve your photography to massive heights. And you can do that by truly immersing yourself into photography. Always keep learning, stay humble, and hustle hard when you’re in the streets.

The next time you face an obstacle in life or street photography– know that it is an opportunity to improve yourself, to motivate yourself, and to break outside of your comfort zone.

As Marcus Aurelius said, “The obstacle is the way.”

If you are interested in overcoming more obstacles, I’d recommend reading: “The Obstacle is The Way“.

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