Being able to control your shadows when taking a portrait is both easy and important as long as you have the right equipment and knowledge. This video really helps illustrate the technique of being able to use your off-camera flash to both soften the shadows and make them more manageable. If you're using an on-camera flash, you won't have as much flexibility, but the principle remains the same and you can use this technique when using the sun as your key light too! Unless your subject is just really, really, really ugly... I'm talking shaved dog butt walking backward kinda ugly (I don't even know what that means!), than you probably don't want their face covered in darkness, but that's your call.