There are multiple ways to obtain the proper exposure on the face (when back lit) and my favorite is to shoot in manual exposure. Although it can seem very daunting at first; shooting in manual exposure isn't as difficult as it was many years ago.
In this case, I metered for the background but overexposed it slighting to eliminate some of the unattractive far background that couldn't be avoided from this angle. In addition, I wanted the middle ground (barrel and part of the porch post) to be partially scene and not underexposed by too much. (I was using the pole and side of the house to frame him too and I didn't want it to be too dark.)
Sean's mom held the strobe on a pole camera left. I adjusted the output of the flash to light his face but not overexpose it. I used the Nikon SB800 set to TTL and modified the light output of the flash from the commander mode in the camera. This setting enabled me to dial down the flash output by 1 stop of light.
The light from the sun acted as a hair light and gave some separation from the rest of the scene.
If a helper isn't available, then a light stand is an option which works well normally. (When using a light stand, I use my camera bag on one of the legs of the stand to keep it from falling over on uneven surfaces or in the case of a windy shooting environment.)
Get out and enjoy the fun of capturing God's creation!
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