On Failure and Street Photography

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Photos in this article are from my “Grandfather” series.

“99% of street photography, if not more, is about failure” – Alex Webb

Street photography is all about failure. The failure to have the courage to take that one shot. The failure to capture “the decisive moment.” The failure to get a clean background. The failure to have your subject make eye contact. The failure to move your feet to get a better frame. The failure to get recognition for your work. The failure to have your photo get “explored” on Flickr. Failures upon failures upon failures.

I think one of the things that initially drew me to street photography is just how damn hard it is. It was unlike any other form of photography out there. It was so unpredictable. Whereas when I shot landscape, macro, or architecture– I could take however long I wanted, and I had so much in my control. But with street photography, I had to learn to relinquish control to simply “go with the flow.”

I couldn’t control the light, control how people looked, the background– all I could control is how well I could move my feet, and click the shutter at what I thought would be the “right” moment.

I’m currently staying with my manager Neil Ta at the home of Gareth Jones and Savlatore Gullifa in Amsterdam– and I had a conversation with Gareth about the constant disappointments and failures that the both of us have in street photography. But I came to realize that it was our failures which lead to our successes– and how disappointment was a sign that we were progressing in our photography.

For example, when I started street photography– I thought all of my photos were absolutely amazing. But when I started to look at the work of the masters before me, I soon became disappointed in my work. I felt like every photo I took was an “almost” photo– and that I would fail constantly, over and over– to get that one “perfect” photo.

But in street photography (and in life) there are no perfect photos or perfect moments. They are all imperfect in little ways. Imperfect in terms of the frame. Imperfect in terms of the moment captured. Imperfect with random things dangling around the corners of your frame.

But I think it is in those imperfections come beauty. And not only that, but we need to constantly fail in order to become better. It was Thomas Edison who said: “Genius is one percent inspiration, ninety nine percent perspiration.” We need to sweat and fail in order to improve, and move ourselves to the next level.

Personally I see myself as a failure in street photography in a lot of different ways. However I have learned from my failures– which help me become a better photographer. Here are some examples:

1. Failing to take the photo

My grandfather’s resting place before he passed away. Part of my “Grandfather” series.

I have missed countless moments because I was too nervous, scared, or hesitant to take a photo of someone on the streets. But whenever that happens, I tell myself that I won’t hesitate the next photo– and not have regrets later on.

Therefore I build up on my failures to take a photo of someone to build up my confidence. I don’t want to continue to fail taking a certain photo and regretting it. So I try to live without regrets, and just take a photo (and not worry so much about the consequences after). And generally, nothing bad ever happens.

2. Failing on my projects

My grandfather as a younger man. Part of my “Grandfather” series.

I have started countless projects that I have never published online because they all failed. They either failed to materialize, failed to produce interesting images, or failed to have a cohesive idea. For example, I have tried to work on the following project ideas:

  • Airports
  • Cars
  • Babies
  • Stuff on the ground

I have also failed to take any interesting photos in some of the countries I have visited.

But it is those failed projects that have lead me to work on the photography projects I am now more interested in. By failing to work on a certain project tells me that either that project isn’t easy to photograph or uninteresting in general.

So by process of elimination, I have been able to focus on some projects that have been interesting or meaningful to me. They include the following:

There is a saying in the online startup world that says: “Fail fast, fail often.” Once you fail quickly, you can quickly move onto better and more interesting things.

3. Failing to be liked by everybody

My family bowing before and honoring the spirit of my Grandfather. Part of my “Grandfather” series.

I am blessed to have you to read this and a strong following on social media. But still, I always fail to get recognition from other photographers. No matter how hard I work in my photography, there are always photographers I disappoint, other photographers who hate my work (or hate me), or people who hate my blog, my YouTube videos, etc.

I want to be liked by everybody– but I have discovered that is simply not possible.

There is a saying by Roman philosopher Publilius Syrus who said, “To try to please everybody is to please nobody.” I have found this to be true both in my photography and my life.

By failing to meet people’s expectations– I start to focus inward: on my personal expectations. Over time, I have began to care less of what other people think of me and my work. Of course I still want people to like my photography, and I constantly get critique from people whose work I admire and trust. But it is for me to achieve to the most of my personal abilities and standards rather than to simply please others.

4. Failing to make interesting photos

My family marching towards my Grandfather’s grave. Part of my “Grandfather” series.

It is very rare that I take a good photo. In my opinion, I might take one good photo a month, and one great photo a year. That is the expectation I set for myself. And often, I don’t even match that. It might be 3-6 good photos a year, and often I don’t think I ever make any great photos. Out of all the photos I have taken, the only two photos that really have embedded themselves inside me are my “Red Cowboy” photo and “The Sunbather” in Marseille.

I always strive to take interesting photos, but most of them simply aren’t very interesting. But I have learned this to be a good thing– is that I set my bar pretty high for myself, and only try to share my best work. This is why I don’t share that many photos– is because I simply don’t have that much great work to share.

But I’m glad that I fail regularly– because it gives me the motivation to try even harder in my work. I have tons of “almost” photos photos that “almost” work but don’t work because of a small distraction in the background, or moments where I caught the photo half a second too late.

But every time I fail to make a strong photo, I always get one step closer to taking a truly great photo.

5. Failing to go out to take pictures

A crane covers my Grandfather’s grave with soil. Part of my “Grandfather” series.

Another thing I fail at is to go out often enough to take photos. Ironically enough– even though I am a “full-time” street photographer, in-between blogging, making videos, answering emails, traveling, helping out my friends and family– I have a hard time making time to take photos.

I would love to have huge blocks of time when I can go out and simply shoot, but most of the time my schedule doesn’t permit it. I am often running around running errands, or doing things during my day which prevent me to just relax and take photos.

But what I have learned instead is to integrate my life with my photography– rather than simply trying to separate them. When I am traveling it is easy for me to spend all day taking photos. But when I’m at home, I make it a rule to always have my camera with me (regardless of where I go).

I carry my camera to the most mundane activities. I bring my camera when I’m buying groceries (taking photos of stuff for sale or other shoppers), I take photos after dropping off my girlfriend Cindy to school and around UC Berkeley Campus, I take photos when I’m sipping on a coffee at a Cafe, or even when I’m driving (I either pull over and take a photo, or even sometimes take photos while I’m stopped at a traffic light). I even started a photography project at the gym I work out at– simply tossing my little Ricoh GRD V in my gym bag and taking photos of some of the guys working out.


Self-portrait. Part of my “Grandfather” series.

I think failure is something I always fear– but something I have learned to embrace. I find that there are moments of fear that I always feel– when it comes to taking photos, sharing my work with others, or not getting admiration from others.

But every time I fail in something– it gives me more information, inspiration, and motivation to better myself and my photography.

I am the biggest failure in street photography, but it are those failures which help me re-evaluate myself and learn from my mistakes. I hope to one day aspire to be great, but I still have a lot more failing until I get there.