I love street photography. I love the energy of it. I love the unplanned immediacy of street photography. I love the connection between the photographer and what’s taking place within the frame, and I love the connection between the viewer and the image itself. When you look at a good street photo, the photographer disappears — it feels as if it’s just you and what’s happening in the photo, unfiltered by any photographer. I love street photography.

Wait, let me amend that — I love street photography when it’s done well. But here are a couple of true things: first, it’s really difficult to do it well. And second, it’s even more difficult to do it well with consistency. Good street photography is hard. Bad street photography, on the other hand, is incredibly easy.

I should also point out that although I love street photography, I’m not a street photographer. I sometimes shoot photographs on the street (though I’m more likely to shoot in alleys), but street photography isn’t entirely about location. It’s about the ways people inhabit and move through public spaces. Most of the photographs I shoot in public spaces are urban landscapes. If there are people in the photographs, they’re incidental.

That said, I often see good street photographic moments when I’m out noodling around. I’m a completely fucking brilliant mental street photographer. But brilliant mental street photography doesn’t translate to the camera. It’s one thing to see a street moment and think ‘There — that’s it.’ It’s entirely another thing to anticipate that moment, put yourself in the right spot, and have your camera ready to shoot it. That’s one of the reasons I’m not a street photographer. I’m just not willing to walk around with a camera always at hand, ready to snatch that exact moment when everything comes into alignment.

But last week, as I was wandering around downtown, it occurred to me that I do always have a camera at hand. My smartphone. It’s not a great camera, but so what? It’s quiet and unobtrusive, which is pretty important for street work. I have an app called Lenka that shoots basic black-and-white images. This clearly isn’t the optimal arrangement for street photography, but it’s what I had with me. You have to work within your limitations.

I set the app to allow me to take a photo by pressing the volume button on my phone (so I wouldn’t have to fuss about with using the phone as a viewfinder) and went off try some street. Almost immediately, I came across a small group of folks learning to be blind. The headquarters of the National Federation of the Blind is located downtown, and I assume that’s why we so often see a group of blindfolded people with canes being escorted around town. I took a couple of shots without looking.

They weren’t great photos, but they were enough to encourage me to keep trying. I wandered around, saw some interesting folks, took some shots. I tried not to focus too much on people who looked interesting, because those were mostly folks who were marginalized because of addiction or abuse or weight or some other social condition. I tried to look for visually interesting situations instead.

Then I ran into this old drunk guy.

He immediately panhandled me, asking for spare change. I don’t carry much money; I use a debit card for everything. The only cash I had was a couple of twenties. So I told him I didn’t have any change — and I surreptitiously took his photo without looking. Shameful behavior on my part. Doubly shameful in that the photo was blurry.

The guy grinned and offered to take a twenty, which was a nice move on his part. It made me like him enough that I wanted to give him something. I told him I was heading for the drug store across the street and down the block, but if he was around when I came back that way, I’d hand over a little something — and I surreptitiously took his photo again. Still without looking; still shameful. This time the photo was badly exposed.

So I went to the drug store, bought a cupcake for myself and a chicken salad sandwich for the old drunk guy. When I came out of the store, the ODG was hobbling across the street with his walker. I’d told him I was going to give him something and dammit, he was going to make sure I didn’t forget. I gave him the sandwich and a couple of bucks (and yes, I knew he’d spend the money on booze). Again, I surreptitiously took his photo. Again, it didn’t turn out well; badly expose and blurry.

That’s what you get for shooting without looking, I suppose.

Having done my part to support the local alcoholic community, I kept on wandering and shooting. Every so often I’d stop and find a place to sit and chimp the photos. Most of them were bad. Some were really bad. But mostly I was okay with them. If nothing else, I was learning to get the framing right. Mostly. Partly. That’s hard to do when you’re shooting from the hip.

The light was getting increasingly harsh, the shadows were radical — great conditions for urban landscape photos, but not what you’d call street-friendly if you’re relying on shooting blind with a smartphone. Almost everything I shot was badly (or weirdly) exposed.

I decided to end the experiment. I knew a nice, quiet, dark space nearby (okay, let’s just call it a tavern), so I headed there for a cool drink and a chance to evaluate the photos. On the way there I came across the old drunk guy again. He’d taken off his shoes, put them in the basket of his walker (along with the uneaten chicken salad sandwich), and laid himself out on a public bench for a nap. Or to sleep it off.

And hey, I took his photograph one more time. Shameless again.

I learned four things from the experiment. First, I’m not a good street photographer. I’m okay with that. I’m not a rotten street photographer either. I can improve. If I decide to. Second, street work has a moral component. In the U.S. you pretty much have the right to photograph anything and anybody in the public arena. Doesn’t mean you should, though. Third, if you have a moral discussion with yourself before you shoot a photo, you’ll probably lose the shot.

Earlier I mentioned I tried not to focus too much on people who only looked interesting, because they tended to be folks who were marginalized in some way. Shooting photos of those folks would (or easily could) be exploitative — even if that wasn’t my intent, and even if I never showed the images to anybody. It would, in effect, be turning them into props; it would not be treating them as people.

There was a specific moment during the day I made a rule for myself. Shoot first, decide later if the photograph was ethical. Here’s how I came by that rule. I saw another drunk guy. The old man I’d met earlier was clearly an alcoholic, but he seemed pretty self-aware of his condition. He was friendly, with a sort of style and charm about him. He was clearly intoxicated, but not sloppy drunk. He was a sad case, but he was in control of himself and I liked him.

The other drunk guy was probably in his late 20s. He was staggering drunk. Oblivious to the world drunk. Slobbering and probably in dubious control of his bladder drunk. High school drunk. There was nothing likable or charming or self-aware about him. I could feel compassion for him and his situation, but I still recognized he was pretty disgusting. And he was heading up the sidewalk toward the public library.

I hurried to catch up. I didn’t feel any need or desire to photograph the guy himself, but I thought it might be interesting to photograph the reactions of the people he met in the library. I took a single shot when a library patron came out of the library as the drunk guy approached. And then I thought it would be cruel to photograph those reactions; it would be demeaning to the drunk guy himself, and to the people he encountered. The photos wouldn’t be about anything but condemnation for a man who had some serious problems.

So I turned off my phone and put it in my pocket. I felt I’d made the right decision when, as these two guys approached each other, the library patron looked completely repelled. But as they got closer the library guy’s face shifted from loathing to concern. He stopped and spoke to the drunk guy; I couldn’t hear, but I assume he was asking if the drunk guy was okay. The drunk guy just lifted a hand — maybe in acknowledgement, maybe in denial, maybe a suggestion that the library guy should mind his own business, I don’t know — and he just kept zombie-shuffling toward the library.

I’d turned my camera off. I missed that shot. It had the potential to be a truly good street photo. It was a strangely non-judgmental moment. Almost sweet, on the part of the library patron. And that’s then I decided shoot first; decide its value later.

I said I learned four things from the experiment. Here’s the fourth: a sincere attempt at street photography (for me, at any rate) is oddly dissociative. It’s a combination of being very aware of yourself and the world around you, yet being somewhat removed from it. Until — and this is the freaky part — until you see the elements of a photo possibly coming together. At that point you become intensely aware. Of everything. The light, the geometry of the background, the spatial relationships of what’s in the frame, and you start plotting vectors of interception — where it’s all going to come together and where you need to be at that point to shoot the photograph. And it’s both exciting and terribly frustrating because oftentimes you’re also hyper-aware that you’re almost certainly NOT going to be in the right spot at the right moment and you’re going to miss the shot.

I love street photography — when it’s done well. I doubt I’ll ever be terribly good at it, but I’ll periodically continue the experiment. If nothing else, it’s great fun.