Todd, I'm with you - I feel kinda feeble when I try it, but...
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Street is a tough genre to crack, alot of folks can shoot pics of people crossing the street, people in the street or sidewalk but to create a good street shot there needs to be some serendipity invloved. As said above it needs to pull you in, capture or hold your attention.
Can't compare to 60 or 70 years ago but I shoot a lot in New York and there are people engaged with each other everywhere, or engaged with the city itself or just doing their things. There isn't a lack of opportunity.
I think Todd hits it on the head with serendipity but I think there are ways to make yourself more or less open to these moments and capture them when they do occur. To me this is the skill of street photography.
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