Street photography is a bit of a mystery to me. Probably because its origins are surrounded in mystique and filled with famous names and even more famous photographs. But what sets an iconic street photograph apart from just an average or a not very good one?

This is not a screed or meant as any disrespect to the many greats, past or present, of street photography. Rather, it is an indictment on my own lack of knowledge, confidence, aesthetic, and just plain ignorance of what makes one street photograph shine and another just a boring piece of shit.

I’m not quite sure what the allure of street photography is, but I seem to be infected with it. I have many photographer friends who never stalk strangers on the streets and they don’t see the appeal whatsoever. To me, it represents the very essence of photography. To capture a moment in time, never to be seen again, seems magical to me. But what makes one of these moments more appealing to a greater number of people from the next picture?

There are street photos I’ve taken that I imagined would garner praise and slaps on the preverbal back, only to be met with disinterest, or worse, derision. Then I show a pic I think is just so so and people’s reactions are like, “That’s my favorite pic of yours.” It’s a mystery, and frankly, pretty damn frustrating.

Let’s take the below photograph as an example:

This is my favorite street photograph I have taken. I shot it in San Francisco on Tri-X film using my Leica M6 classic. What I love about it is the generational juxtaposition. The older couple, both dressed in black, hovering under an umbrella, locked arm-in-arm. While the younger couple on the left wear lighter colored clothing and only have hoods over their heads and stand apart from each other. To top it off, the two pairs are nicely separated by the old steel alarm box.

I entered this photograph in the SF Street Foto Festival contest in June of 2019 and was confident of winning in the film category. It didn’t get so much as a yawn from anyone. I believe it is this experience, more than any other, that has sent me on this road of doubt and uncertainty. A few months into 2020, in the middle of the Ro-Ro, I pretty much stopped taking street photographs altogether. Somewhere inside I decided it just wasn’t for me. But in truth, I was just being a coward.

Fast forward to December of 2022. I decided that I had had enough of taking only black and white photos and I bought a brand new Leica M11 from B&H Photo. I put my M10 Monochrom up for sale on Facebook Marketplace and decided to give color another go. But something gnawed at me. That same uneasy feeling when I stopped shooting street photography. It was the feeling of giving up again. So I returned the M11 a week later, took down my M10M listing, and decided to go all in for 2023. My goal is to shoot exclusively with the M10 Monochrom and do a lot more street photography. [UPDATE: This lasted about a month]

The first week in January, my wife and I took a trip down to San Diego. We ate breakfast in Ocean Beach and then hit the streets. The rush and excitement from shooting street photography flooded back into me. I struggled at first, but that’s the thing about street photography. It’s hard. It’s not easy capturing interesting candid scenes of strangers that happen in the blink of an eye. Not to mention, I struggled with my settings a bit.

This is probably my favorite shot of the day:

After returning home, I ventured down to Old Sacramento on a rainy Saturday morning. I walked around shooting street for a couple of hours and came away with a surprising number of shots that I liked. They may not be great street photographs, but what I’ve finally learned is that the street photographs that touch me, that move me, those are what good street photographs are. Not winning contests, not copying others, but being true to yourself and enjoying the photographs for myself.

Here’s a sample of images from Old Sacramento:

Now, from everything I’ve learned by reading, watching YouTube videos, and taking in-person workshops from Alan Schiller and Matt Stuart, the photographs above should have what it takes to be considered good street photographs. But does it really matter? I started taking pictures seriously in 1999, way before social media and affordable digital cameras. Did I shoot back then in order to share my pictures across the globe? The answer is no. I was shooting for myself. And I felt good when I took a photo I, alone, was proud of.

So for 2023, I’m going to try and de-program myself from the social media infection and share pictures that I love. If others find joy in them, then that’s just a bonus, but it’s not the goal. Like all aspirations, this will not be easy, but rather accomplished step-by-step through consistency and perseverance.