I think that maybe the trick to doing a (good) portrait is to see oneself in another person. That may seem obvious. That may seem facile. But I’ve got to look at you like I’m looking in a mirror, I mean really looking.
When I really look in the mirror I see myself in all my facets and all my phases. I see the child version of me, the young adult, and the me I am today. I morph between those versions and see the evolution like an animated GIF.
When I look at a person I am photographing I sometimes see the child in them. And I imagine them on some playground, running, swinging, laughing in the joy of their youth. If that happens (and it doesn’t always) I know I’m going to get great photos.
When I say “great photos” I mean photos that will stop me in my tracks. Photos that will feel timeless, and deep. That’s what I’m hoping for.
So, surrender to the moment and regress. Become that kid again. Show no fear. We’re just a couple of children meeting for the first time on the playground.