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—There are no softboxes. Look around the next time you're out and about, and you'll probably not see a single softbox. You'll see all kinds of specular light sources, from tungsten bulbs to halogen spotlights. You'll see light that bounces around a room, and light that pours in from open windows, directly or not. But you won't see softboxes. So to create natural lighting, shy away from softboxes and choose sources that more accurately match the lights you actually find in the real world—and in the particular scene you're shooting.
—Light is never white. White light exists in a RAW processing workflow, when it's been deliberately matched and balanced and calibrated… and often removed of all character and uniqueness. Mr. Heisler said he learned in his early days working on movie sets to always gel his lights. He imparts some color, some warmth or coolness, to help set the scene and tell the story. So I've been trying to gel my lights more often, whether it's a strobe in the studio or the flash on my camera. If you're not sure with which gel to start, consider something in the orange family to add a bit of warmth to skin tones.
—Create the illusion of reality. Mr. Heisler showed a portrait of Bruce Springsteen, made next to an open window through which sunlight poured. He then divulged that the shot was made long after dark, and he had created the sunlight from scratch. The light had a purpose, though, as it appeared to come in through the window as natural sunlight. This upped the feeling of reality in a way a light with no purpose, no tie to reality, ever could have.
—Simple lighting is good. Sometimes, though, simple lighting is actually very complex to achieve. As in the above story of The Boss by a window, Mr. Heisler and his team went the extra mile to make the image appear simple and natural. Don't hesitate to create lighting that doesn't hit you over the head with how complex it is—even if it's really complex to create.
—Complex lighting can be good, too. Want to make a subtly nuanced portrait with finely controlled highlights and shadows placed just so? That's fine. You can do it, and you can sometimes do it very simply. Lighting that looks complex and nuanced need not be excruciating to create. You can combine a single strobe with ambient light—say, a kicker from the sun—to make fancy-looking dramatic lighting without a whole heck of a lot of trouble. This way, you're free to focus your energy on the interaction with the subject—a surefire way to make better portraits.
—Remember the point of your photo. Don't get lost thinking the medium is the message. If your subject is the main reason for the photo, then you won't get caught up creating "whiz-bang" lighting that's designed only to impress other photographers. Create the ideal lighting—whether simple or complex—to serve your subject and best tell your story.