Not taking the photo
I have never regretted taking a photo, but I always always regret not taking one.
I've been planning to do a series of environmental (large format film) portraits of my close and extended families. The idea is to travel to their homes and photograph them using natural light, if feasible, in their favorite spaces. I would then make two archival silver gelatin fiber prints, one for them and one for me.
I've not done this even once.
Wherever I go, there is a camera with me. It often remains in the bag, unused.
I was walking yesterday and passed a man on the sidewalk wearing a hard hat and face shield which was tipped up so it didn't hit the cigarette hanging from his mouth. He had a great face and I thought it could make a fun photo. But, I was afraid to ask him if I could photograph him and only nodded as I walked by.
I'm ashamed of myself and it makes me want to sell everything and find another hobby.