It’s Wednesday evening, I’m in St. Pete, and I’m about to get a new headshot.

Experience is telling me to expect the worst. Years of self-improvement are telling me to expect the best. And Tommy, the photographer, is telling me to hold an imaginary sandwich.¹

Which, by the way, I’m doing wrong.

“Not quite,” he says at my first attempt. “Pretend it’s a sub and you’re carrying it with both hands.”

He bends his forearms and turns his palms upward, showing me what to do. I copy him.

“Great, but longer,” he says.

I go from a Pub Sub to one of those never-ending sandwiches you see in cartoons. Specifically, this one:

Tommy says I’m almost there. “Now move your arms and elbows out wider, away from your body. Not too much. Yes, just like that! Perfect!”

With the imaginary sandwich in place, my shoulders, arms, and back are photo-ready. The sandwich is to the torso as cheese is to the smile, I guess. Now it’s time to get my head and facial features in position. Turn this. Swivel that. Face this way. Tilt my forehead. Push out my chin.

That’s a lot of things for an uncoordinated guy like me to remember. I can’t quite get everything to be where it needs to be at the same time. At least I don’t drop the sandwich.

Click. Flash. More directions (turn a little that way, give me a roar, adjust your shoulders).² Click-flash, click-flash, click-flash.

And we’re done. Time for the next supermodel to take their spot on the X taped to the floor.

“That wasn’t as easy as I thought it would be,” I say, not accusing him of anything—just acknowledging my overall clumsiness.³

“Don’t worry, you did great!” he says. “You’re going to be happy with the results.”

I hope he’s right.

Inner Saboteur

My last headshot was taken in 2015. Back then, I was very down on myself. All I saw in photos was faults and flaws—some real, but most invented or exaggerated.⁴

Low self-esteem is the most bitter, cutting drag queen you’ve met. She’d shove that photo in my face:

You’re not perfect.
You’re not beautiful.
You don’t look like Linda Evangelista.
You’re not a model!
Nothing about you is perfect.⁵

Well, I guess she’s right, I’d tell myself, handing her a ten-dollar bill and thanking her. What an honor to be read to filth by a professional!

Healthier Outlook

I’m healthier—mentally and physically—than I was 10 years ago, but I still have a difficult relationship with photographs. I enjoy seeing myself in them now, because they remind me of how far I’ve come.

Old Dave pops up occasionally, but he doesn’t bug me as much. Yet I’m still apprehensive as I say bye to Tommy. A headshot is important, especially in the world of remote work and LinkedIn, where you have just a few pixels to make a first impression. What if, after all this time, a professional photographer with expensive equipment surfaces all the things that brought me down before?

That doesn’t happen.

Tommy did a great job positioning and shooting me. And I need to give myself credit, not just for doing the work to feel and look better, but for learning how to see the whole picture—pun intended—instead of letting the drag queens zoom in and distort the details.

And Now … The Results!

My Favorite: The Broad Smile

A Great Alternative: The Gentle Smile

One I’ll Never Use, But It Cracks Me Up: The Stern Expression

Picture-Perfect Footnotes

1. Tommy Lacey is a St. Pete-based photographer and videographer. He offered headshots at a recent American Marketing Association/Tampa Bay meeting. A lot of attendees were, like me, impressed with his work. If you follow AMA Tampa Bay members on LinkedIn, you’ve probably noticed a wave of Tommy’s headshots in the last week or so. ↩︎
2. I attempt to roar. The result is not unlike Tony the Tiger channeling Bert Lahr. ↩︎
3. I can chew gum and walk at the same time. That’s the upper limit of my choreographable abilities. ↩︎
4. The photo itself is strong. The photographer has a natural eye for composition and lighting. She turned a blackboard into a creative background that added a lot of texture to the image without stealing focus from the subject. The issue has nothing to do with the picture, but with the guy who’s in it. ↩︎
5. I am, of course, misquoting Aja’s epic Werk Room rant against Valentina. Don’t forget the remix! ↩︎