How do you capture several emotions at once?

I hate taking flights on holidays. I might be the only one on this, but I hate taking flights or doing anything commercial on major holidays like Christmas or New Years.

It bothers me to see people having to work and serve me on a holiday while I get to run around and spend time with family and friends. I was telling a friend about this recently, and with both of us flying on Christmas, I put us up to carrying a bag of Dove chocolates to hand out to employees as they helped us get home. But the morning of my flight, I forgot my own bag on the counter as I left. Great.

My friend challenged me to give out them out instead on the streets when I got back. As I slowly gave them out, I met Robert at the Union Gospel Mission. It turns out, Robert was a former SEAL (he had the ring to prove it), and a few bad decisions plus a deteriorated relationship left him on the streets. He thought himself above holding a sign to get by, but out of despair and the urging of a friend, he started.

Robert said he made just barely enough, and that it was a pitiful existence. He spoke to me of the twisted faces he would see through car windows as people would dodge eye contact for two minutes waiting for a light — or perhaps no expression at all, as people would pretend he didn’t exist.

Soon enough, Robert started to believe them too…

This is something many of us encounter on the other side. I wanted to capture that sense of uncertainty many feel when they see a need and don’t know how to respond. So with Robert and my friend Diego’s help, we tried to take a few photos to depict that experience.

You can view the six images in higher-res here. Which photo stands out most to you? Why? What could I do better the next time we shoot? Love to hear your thoughts.