When I started out as a photographer I was way too shy to take portraits of people I didn’t know. I mostly shot architecture. It was lonely. I decided I needed to change. I gave myself an assignment to hang out in parks and take portraits of people. The two rules I gave myself were 1) I had to ask if I could take their pictures, and 2) the more awkward I felt about asking them the more I forced myself to. At the beginning of this exercise it would sometimes take me 30 minutes before getting the courage up to approach – I would follow them through central park at a distance hating myself – feeling like a stalker. I worked on this more and more till I felt comfortable approaching strangers.
In New York people say yes 99% of the time when I ask. I tried the same thing in Miami and people also said yes – but thought I was trying to pick them up. In LA it’s hard to get close enough to people to be able to ask.