Street photography can be either easy or extremely difficult, depending on what you your expectations are. There are of many forms and aspects to street photography. Here I want to speak briefly on an aspect of comparison that are polar opposites to one another.
On one extreme, we have street photography in its most general and random form. These are pictures of random passer-bys walking on the street. That you have successfully captured a fleeting moment of a random pedestrian’s life in a picture is cause for celebration. Indeed there seems to be a healthy number of photographers and fans who enjoy this style of street photography.
The practitioners of the opposite extreme consider the work of the former style to be uninteresting. A picture needs to tell a story, has some meaning to it, evoke some emotion or thought in the viewer. Unless it is a carefully composed street portrait, pictures of random people on the street are boring. The ultimate goal is for a picture to have the elements of a thoughtfully composed painting, a feat most worthy of celebration. This style of street photography is extremely difficult, because you end up discarding a lot of photographs you feel is not interesting enough. You could be shooting for weeks, and still not have anything you feel is worth sharing with an audience. However, the joy of finally getting something that satisfies you is wonderful, as you know you have achieved something that is subjected to a set of personal quality requirements and might just get even stricter as time goes by, something not everyone is willing to impose on their output.
I suppose that I fall into the second category of street photographer. A difficult pursuit, yet thoroughly enjoyable. – WY