5 Reasons Your Headshot Didn’t Turn Out as Planned

You had your headshot taken. You smiled, you stood where you were told. The lighting looked fine, but the final image? You don’t like it.

You’re not alone.

As a headshot photographer here in Chicago, I hear this all the time: “I’ve never liked a photo of myself” or “I’m not photogenic.”

The problem isn’t your face, it’s the process.

Here are 5 common reasons people end up hating their headshot, and how to make sure your next one is a photo you actually want to share.

1) Nobody Helped You With Your Expression

One of the most overlooked part of a headshot session is expression coaching.

Most people aren’t naturally comfortable in front of the camera. You need direction. Subtle feedback on how to shift your eyes, mouth, and posture. Otherwise, you’ll end up with a smile that looks forced or a stare that looks blank.

A professional headshot should show confidence, approachability, and professionalism. That takes more than saying “cheese.” This is a major factor that separates photographers.

2) You Didn’t Know What to Wear

Clothing makes a bigger difference than most people realize.

What looks good in person doesn’t always translate on camera. Certain patterns, necklines, and colors can compete with your face or throw off the lighting. If your photographer didn’t give wardrobe guidance, you were left guessing.

I used to consult people beforehand on clothing, but now I tend to lean into bringing whatever you can. We can’t shoot it if you don’t bring it. And while there are some guidelines to follow, some clothing will surprise us!

3) The Lighting Wasn’t Designed For You

Not all Lighting setups work for all faces.

Flat lighting can wash you out. Harsh shadows can emphasize features you’d rather not spotlight. And poor white balance can change your skin ton entirely.

An experienced Chicago headshot photographer will use lighting that’s tailored to your face shape, complexion, and overall look. That’s what separates a studio portrait from a polished professional image.

I have 2 main lighting set ups for my headshots, and each time it’s adjusted for the individual in front of my camera at that moment. While I love my 2 setups, it doesn’t mean they work for everyone!

4) You Felt Awkward the Whole Time

You’re not an actor or a model. You’re a real person trying to look professional, but not stiff.

If the photographer didn’t make you feel comfortable or walk you through the process, that tension shows in every frame. It can make even the best lighting and best retouching fall flat.

The best headshot photographers know how to make people relax. They ask the right questions, make the right jokes, and actually pay attention to how you’re feeling.

Ever have someone ask you to flex your pinky toe while getting a headshot taken? Didn’t think so! But for that split second, you forget about having your photo taken.

5) The Session Was Rushed

You need time to warm up, and that’s okay.

If you were in and out in 10 minutes, it’s no surprise the result felt generic. Rushed sessions leave no room for coaching, multiple looks, or experimenting to find your best angles. There have been times where we get lucky, and those first couple images turn out incredible. But even in those cases, more time equals more comfort and genuine expressions.

High-end headshots take time. Not because the setup is complicated, but because people need space to get comfortable in front of the camera. You need to get comfortable with each other. You need to see results to make sense of all the things you’re being asked to do. Once you see how good the images are turning out, it helps everyone relax.

What’s the fix?

It’s not about being photogenic. It’s about having the right process.

When I shoot headshots I focus on expression, body language, lighting, and wardrobe. I coach you the entire way and you see the images as we go. We don’t wrap up until we’ve got something that looks like you, on your best day.

If you’ve hated every headshot you’ve had so far, maybe it wasn’t you.

Maybe you just haven’t had the right kind of session yet. Book your session here to give it a second try, or maybe third.