Los Angeles Headshots taken by Willie Diggs
Don't let someone transform you into something you are not. The best headshot, for you, should represent how you really are and how you want to represent yourself. The biggest mistake people make is not being themselves.
You need to represent yourself in whatever category you fall into. Stick with the market that your looks are going to work for. If you look like the rugged bouncer or security guard, then gear your shots toward that market. Don't try to transform yourself into the intellectual or the nerd type. People may influence you to transform yourself, but the headshot that is going to represent you best is the type of person you already are.
You must also be aware of the post production process, you do not want to misrepresent yourself through excessive retouching. When you walk into a casting office the casting directors want to see real natural emotion from your headshot, they do not want to see a picture that is touched up so much that it does not even look like you. Making very minor touch ups are fine, but doing too much will reflect badly on you. If you ask for too much retouching, your picture will no longer look like you. You have now transformed yourself into a perfect looking version of yourself. This may look great, but in reality you are deceiving people by misrepresenting how you really look.
After determining who you are, how you want to represent yourself, and what the majority of people think you will be cast as -it is up to you to be yourself. During your headshot session, be relaxed and give off real natural emotion. Think of things that really make you feel angry, happy, sad, confused, confident, cocky, animated, and so on. Be yourself, be real, and be natural and you will reveal the best headshot for you.