Confronting challenges, overcoming social anxiety, stepping out of my comfort zone; are three of the main factors I get from experimenting with street photography.
How I got this picture I came across with this shot as I was doing a photo walk late in the morning, just before noon. My eyes were immediately drawn to him as he was enjoying the sunlight outside of a senior home. I had my camera set in zone focus mode; my initial plan was to shot from the hip, then I realized he noticed my presence, so I brought my camera to my eye level and continued shooting. At that moment, I felt compelled to smile and ask for a closeup portrait to which he smiled back, and said: "sure!" and this was my favorite shot from the set. I was careful not to crop any of his extremities, like his feet or the top of head; and in the midst of the shooting process, I felt that showing his walking cane was essential to the image, so I made sure to leave it
Having had this experience taught me to be more transparent when doing street photography, people can sense what you're up to, so keeping a smile the entire time can increase the chances to have a decent shot. After all, it is true that a positive attitude goes a long way.
As I stop to think about it, something I would have done differently is to have a conversation with the person. Asking his name or his preferred choice of pipe tobacco brand could have been an excellent opportunity to add value to the final result; so I hope to find him again next chance I get to do a photo walk and do just that.