This keeps happening: I hear about someone or speak with someone and then I go to their website to check them out and they have a picture of themselves posted. Which is fine, except that then when I meet this person I hardly recognize him/her because the photo was obviously taken 20 years ago! Come on! Do they really think people aren’t going to notice the difference between the photo at the website and the way they actually look? Keep your photo updated. I lose respect for these people, because they are in effect lying to you at their website.
I don’t think you need formal headshots anymore (unless you’re trying to become an actor). The world is a more relaxed place these days. Get a blog. Put a picture of yourself up there every few weeks or months. Keep it current. Tom Peters, who I work with, posts pictures of himself on occasion in his blog. One was a self portrait taken at 4 in the morning in celebration of St. Patrick’s Day. Kind of scary, but elicited a lot of fun comments. And then more recently Tom’s wife took a picture of him outside at his farm. He’s wearing a baseball cap and a San Francisco Giants warmup jacket. It’s a good picture. Tom looks relaxed. He looks good. And he looks like what he looks like right now, not what he looked like 20 years ago.