If you’ve ever thought, Wow, I wish I could have a photo of myself that makes me look simultaneously terrified, regretful, and a little constipated, then you, my friend, are in luck. Because today, I’m going to walk you through how to take a truly terrible headshot—the kind of photo that will live in HR databases long after you’ve left the company and will surface unexpectedly in professional presentations for years to come.
And I know this, not because I read a book on the subject, but because I have survived it. I have spent years taking headshots and watching people—rational, functional, intelligent people—self-destruct in front of a camera. I have also, tragically, done it to myself. I have pulled every one of these stunts at some point, and I have seen them performed with heartbreaking commitment by others. This isn’t theory. This is lived experience.
Step 1: Buy the Most Expensive Equipment You Can’t Operate
The first step in taking a disastrously bad headshot is to invest heavily in cameras, lenses, and lighting equipment that you absolutely do not understand. Ideally, you should have a setup so complicated that NASA would call to ask if they’re doing it right.
You’ll want a backdrop that suggests power, like a stormy blue-gray or something vaguely reminiscent of a Renaissance oil painting—because nothing screams relatable executive quite like pretending you’re being painted by Rembrandt.
Of course, you’ll also need a studio that exudes importance. This means a lot of furniture that no one actually sits on, art books that have never been opened, and music that makes people question their life choices—preferably moody electronic beats that say, I may be a photographer, but I also DJ at obscure Berlin nightclubs on the side.
Step 2: Show Up in the Worst Possible Condition
Now that you’ve set the scene, it’s time to sabotage yourself completely before even stepping in front of the camera.
Here’s how:
- Stay up all night, preferably staring at a spreadsheet full of numbers that mean absolutely nothing to you. Bonus points if you weren’t required to make the spreadsheet, but felt compelled to do it anyway.
- Reconsider every decision you made for this headshot. Wonder if the blue blazer was a mistake. Debate whether the gray one would’ve been better. Spend a full 45 minutes on Google researching “power colors for executives” and feel your confidence erode in real-time.
- Doubt everything. Are your glasses too distracting? Should you have gotten a haircut? Are you even ready for this photo, or should you delay it by another six months until you “feel more like yourself”?
By the time you arrive at the studio, you should be exhausted, over-caffeinated, and entirely convinced that this headshot will determine the rest of your professional life.
The goal here is to look like a person who has just finished a grueling interrogation—the kind where someone keeps offering you a glass of water but won’t tell you why you’re being detained.
Step 3: Convince Yourself That You Are in Control
This is where most people ruin themselves completely.
You arrive at the shoot thinking, I know how to look good in photos. I’ll just be natural. Relaxed. Effortless.
And then the camera is aimed at you.
Your entire body forgets how to function.
Your arms suddenly feel too long.
Your face, which has sat on your head without issue for decades, now feels like a mask you do not remember putting on.
Your brain, once a functional organ, now only produces one looping thought:
What do I do with my mouth?
At this point, panic sets in. You try to hold still, but your own existence feels unnatural. You tilt your head slightly and suddenly think, Oh no, was my head always this big?
You start sweating, which makes you look guilty. The photographer hasn’t even said anything yet, and already you have the expression of a man who knows where the bodies are buried.
And then, because things aren’t bad enough, you announce that you always look better in the mirror. Or—better yet—that you once looked fantastic in a dimly lit wedding reception photo, half-drunk, mid-toast, head tilted at an angle you’ve never naturally assumed before or since. In your memory, it’s a masterpiece, but the original file was deleted years ago, so there’s no way to confirm that it wasn’t just the flattering glow of tequila and poor resolution.
Meanwhile, the photographer is still waiting, camera in hand, watching as you begin to mourn a long-lost, possibly imaginary version of your own face.
Step 4: Let the Photographer Micromanage You Into Oblivion
A truly bad headshot requires a photographer who insists on coaching you through every muscle movement in your body.
- Tilt your chin up. No, down. Actually, back up. But just slightly. Okay, that’s too much. Maybe try to look… less worried?
- Relax your shoulders, but also keep them engaged. Strong, but soft. Like… a confident golden retriever.
- Smile, but not too much. We want warmth, not psychopathy. Okay, now… just look approachable. But not too approachable. Somewhere between a CEO and a guy who runs a very successful maple syrup company.
After five minutes of this, your body gives up entirely, and your face settles into the expression of a man being asked a complex riddle at gunpoint.
Step 5: Analyze Every Single Flaw in the Photo
Now comes the best part: The Great Overanalysis.
Load your photos onto the biggest screen you own. Zoom in as close as humanly possible. And then begin spiraling.
- Oh my god, is that a wrinkle?
- Has my nose always done that?
- Are my eyes asymmetrical? How has no one ever told me this before?
- Why is my left eyebrow acting like it belongs to a different face entirely?
Within minutes, you will no longer be a person—you will be a collection of terrible, deeply upsetting details.
Your entire self-worth will now be determined by a single photo that could be replaced with a picture of an egg, and no one would notice the difference.
Step 6: Fix Everything Until You Look Like a Wax Figure
At this point, you have two options:
1. Retouch it yourself until you resemble a low-budget action figure. – Remove every wrinkle, freckle, and pore until your skin has the smooth, rubbery texture of a dolphin. – Slim your face until you have the jawline of a Marvel villain. – Brighten your eyes until you look like you were created in a lab for military use.
2. Use AI to do it for you. – Just a few clicks and suddenly, your face has been replaced by a slightly off-putting digital avatar. – Your skin is flawless, but also plastic. – Your nose has been subtly altered, and now you look like someone in witness protection who doesn’t quite remember their original identity.
Either way, the final headshot now radiates an unmistakable energy: “I have seen things. And I have regrets.”
How to Actually Take a Good Headshot (By Doing None of This)
If you want a good headshot, do the opposite of everything we just talked about:
- Show up well-prepared, well-rested, well-fed, and not in a state of existential crisis.
- Stop trying to control everything. The moment you do, you’ll look like a malfunctioning animatronic.
- Work with a photographer who knows how to direct without making you feel like a wanted criminal.
- Don’t over-edit. Retouching should make you look like you, not like a cyborg from a failed sci-fi pilot.
A good headshot isn’t about perfection. It’s about looking like you—without looking like someone who spent four hours trying to Photoshop themselves into a new personality.
And believe me, I know. I have been there. I have done all of this. And that is exactly how I know how to stop you from making the same mistake.