Dave Shea writes about his new press photo today. His rule about taking a whole bunch of photos so you get something you like is a good one—it's what professional photographers do, after all.
My press photo didn't work that way. Back in January 2001, shortly before I was unexpectedly laid off from my last permanent job, I took a bunch of photos of different people with my Nikon, for the company's annual report. Just to finish off the roll, my colleague Barb Gass used my camera to snap a single frame of me at my desk, leaning back slightly in my chair, with a freshly painted yellow wall behind me. It's not perfect—my shirt is a bit bunched up against the chair—but I liked it so much that I've used it as my official photo ever since—and converted it to black-and-white for my website photo too.
Dave's other rule of re-doing your photo every six months or year also doesn't apply, since I look pretty much the same as I did three years ago (except for that span in 2002 when I had a beard). I even still wear the same glasses.
Perhaps the rule should be to change your promo photo when you change your glasses or hair, when you look noticeably unfashionable, or if you've aged visibly?