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This image blows me away, which is why I asked David Hobby how he lit it.  Be sure to watch our full interview for more of his tips, but this is what he told me about making this image:

That’s a mistake.  A lot of my best pictures are mistakes, and I’ll fully own up to it.  Not a mistake, just something that wasn’t what I planned.

He’s sitting out playing at a lakeside, this is a setup, an environmental portrait, and I’m floating an umbrella right over him.  Just some guy holding a light stand and dropping it down, and I’m filling with an Orbis ring flash, which is my– that ring flash and key light combo is really a go-to thing for me.  And I’m filling in detail, and I turned the ring flash off that was filling in all the shadow detail down at the bottom, and i just want to see what that top light looks like, so maybe we can move it a little bit before we do our finals, and as it turned out the way I was fixing my problem of legibility in the bottom of the frame was also taking away a lot of interest and drama and contrast from the picture.

So as soon as I turned of my second light, that professional second light that fills in all the shadows, I realized that my picture was really this rougher, more stark top-down umbrella right over his head, just let it fall right across him.  But you gotta be willing to say, “That’s kinda better than what i was doing,” and just go with it.

Watch the full Interview with David Hobby,  buy books by David Hobby