On Monday I spent the day with two street photography students, and one of the things we worked on was gaining comfort making portraits of strangers.  A good way to gain confidence in this, if you feel uncomfortable approaching strangers, is to start by making portraits of street entertainers.  When I do this I always carry small denominations of money that I can use to tip the entertainer before I make a portrait.  Street entertainers are artists, and when they are out there they are working.  Sure, you can just walk up and steal a photo of them, but if we are going to include them in our work why not respect their time (and their art) by providing them with a small amount of compensation?  This, plus building rapport through conversation and showing genuine interest in their work, will earn you the time to really spend a few minutes and make a portrait that you are happy with.  If you get something really nice, offer to send them a copy of it.  At the end of the day shooting on the street isn’t just about the photographs that we take.  It is also about the people that we meet, the friendships that we make and the experiences that we have. 👍 .
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