She's in front of a closed shop or something like that. Made for a nice background!
I often need to warm-up a bit depending on how self conscious I feel. Not that I just go around taking random shots, but if I'm too hesitant at the beginning, I'll force myself to click some photos that don't have big potential. Of course, even though are approach is similar, you have probably picked up a lot more useful tricks than I. :)
I love your advice about getting people's emails and sending them good photos! I've been thinking of doing the same, and I may have to.
Noted about the challenges. It will be a lot of fun to shoot with a clear task in mind.
Challenges can definitely help you focus. And if you are at all goal oriented or competitive, they are great motivators...even without actual payoffs outside of knowing that you kicked some serious ass.
One more thing I do when shooting street: if I’m in an area with homeless people or street buskers, etc. I will often carry small bills or change. And I frame that as appreciation, not payment. Sometimes a little respect and conscious eye contact is all someone needs. I see my camera as my eye. When I photograph someone, I’m saying, “I see you. You matter. Thank you for being here.”