I've Updated My Headshot
Like most men the only professionaly taken photograph I've ever had done (outside of when I was a kid and was taken in for family portraits) was at my wedding. It's the only time I, personally, have paid anyone to take my picture. However, in writing, speaking, and training there's the request once or twice a year from publishers or event organizers for a “headshot.” The first such request came back in 2000 for my second book, Designing Active Server Pages. I was home from college at the time and had my dad take a headshot with his company's spiffy (at the time) digital camera, the first one I had actually ever seen or used when he first brought it home several years back. I don't have the picture anymore, but you can probably imagine what it looked like. Just picture what a headshot taken by an unskilled photographer (my dad) with a disinterested subject (me) against a wall in the living room without any sort of lighting check would look like and you pretty much can imagine how that turned out.
The next request for a headshot was in 2001. I had written up a little three-page handout for the ASP Connections Conference in New Orleans for my publisher (Sams), and they wanted to liven it up a bit with my mug on the cover. I had my girlfriend at the time (now wife) take the photo of me sitting at my computer. Sams was obviously not very impressed and decided to try to hide my photo taking skills by making it black and white, adding some racing stripes, and cutting off two of the corners.
You can see my keyboard in the background, and my mouse and mousepad in the bottom left corner.
Sadly, I actually used this headshot for a number of items since then. But then in 2002 I had an actual live, professional photographer come to my house to get a print-quality photo of me! I was one of 40 alums from my alma matter they were doing a story on, and they wanted a photo of each. I think mine turned out the worst. Most of these folks have like real office jobs, so their photos are taken in boardrooms with impressive views with the subject wearing a smart looking office suit. Mine was taken at home with me sitting in from of my chair, wearing an effeminate looking yellow shirt. (The photographer insisted I wear that, he wanted some “color“ in the photo, or something.)
Who would have thought any human could be so excited to be holding a book and wearing a yellow shirt?
So my experiences with photos weren't that good, but at my first MVP Conference they had a “professional” photographer who would take a headshot with you standing against an ideal background, and then email a high resolution image of it to you, all free of charge (or on Microsoft's tab, rather). Visions of having a professionally done headshot were spinning through my head as I waited in line for this great service. Only problem is I was in one of my “Let's go as long as I can before my wife makes me shave” episodes, which had been going on for a while since I had been out of town for a bit under a week. Plus this was taken on the first night there, meaning I had been up since about 6, had been on a plane or in an airport for six hours that day, and had, by this time, a couple of beers in me. Wee!
I've refrained from using this headshot professionally, as I think it makes me look slightly crazed with a slight scent of homelessness.
In 2004 my wife and I got married and, for some reason, she wasn't cool with having my dad take the pictures. (Had she seen the O'Reilly headshot from 2000!?!) We checked out about a half dozen photographers and ended up with a very good one, the wedding photos and album were both amazing, and after a year he sold us all the proofs and gave us several DVDs full of high-res images for a few bucks. So I am contemplating “upgrading“ my current black and white + racing stripes headshot to this one from my wedding:
The only thing I don't like about it is I think it looks like I'm smirking, a la G.W. Bush. But I think it was mostly nervousness with a slight touch of indigestion. (Note to future grooms: abstain from the fish burritos the day of your wedding.) Plus it kind of has that weddingy feel to it, because while you can't really see the tux, it's obvious that I'm wearing something fancier than the usual T-Shirt I don. But at least it's better than my past headshots, although that's not saying much!