Is Your Headshot Working Against You?
Your headshot is working against you.
There's a particular awkwardness that happens when someone meets you in person for the first time after seeing your headshot online. A brief recalibration. A glance, then a second glance. Sometimes they say something — "oh, that photo doesn't do you justice" — and you nod and laugh and move on. But you file it away.
That moment is a signal. And most people get it more often than they'd like to admit.
A headshot that no longer looks like you doesn't just create a mild social awkwardness — it actively creates friction before you've said a word. It makes people trust you slightly less than they would if they'd met you first. It makes your online presence feel slightly stale even when everything else you're doing is current and sharp.
When your headshot is working against you.
Most people don't decide to update their headshot because they've done a calculated audit of their personal brand. They update it because something finally makes the discomfort impossible to ignore. Here are the five signals I hear most often from clients — not as a checklist, but as a way of recognizing something you might already know.
You hesitate before sending it. There's a half-second pause — "this is a bit old" — before you attach it to an email or link your profile.
People do a double-take when they meet you in person. The gap between the photo and the person has become noticeable to other people.
You've changed. A new role, a new direction, a shift in how you present yourself professionally. The photo is from a different chapter.
Your image across platforms is inconsistent. Different photos on LinkedIn, your website, and your bio — none of them current, none of them quite right.
You're using a cropped photo, a conference lanyard shot, or something from five years ago because you never got around to it.
You look at it and think "that's not really me anymore" — and you're right.
Any one of these is enough. None of them is dramatic. But they accumulate, quietly, in the background of every professional interaction where someone looks you up before they meet you.
A good headshot doesn't make you look better than you are. It makes you look like yourself — which is usually better than the photo you've been using.
On what a session actually does
Not a makeover. A recalibration.
People sometimes come into a headshot session with the idea that they need to present a particular version of themselves — more polished, more serious, more professional. That instinct usually produces exactly the kind of stiff, slightly uncomfortable image they were trying to avoid.
What actually works is simpler. The session is an opportunity to make a current, honest image of who you are right now — not who you were five years ago, and not a version of yourself you're performing for the camera. The goal is legibility: when someone looks at the photo, they should immediately get an accurate sense of who they're going to meet.
That's it. Clear, current, and actually you. It sounds straightforward because it is — but it takes a bit of work to get there, and most sessions where it doesn't happen are ones where no one was doing that work.
I'd rather spend the time on that than on telling you how to hold your chin.
— Shawn
When you're ready for a photo that looks like you.
Portrait and headshot sessions in Ottawa & Gatineau. No chin advice included.
