The Headshot I Almost Didn’t Send

A while ago, I was interviewed for Trent Bell and Tim Holt’s podcast, Architecture Design & Photography.

Then came the follow-up email:
“Could you send over a headshot and a short bio?”

Simple enough. Except… it wasn’t.

I opened my folder of “current” headshots and found the most recent one I had—taken about 10 months ago, at least two hairstyles ago. It’s a strong image. Clean light, confident expression, everything technically where it should be. The kind of photo I’d be proud to deliver to a client.

But it didn’t feel like me anymore. Not quite.

And I hesitated longer than I expected.

Because a headshot isn’t just a photo—it’s a proxy. It walks into rooms before you do, introduces you before you speak, and stands in for you when you’re not there to explain yourself. When it’s even slightly off, you feel it in a way that’s hard to name but impossible to ignore.

I almost didn’t send it.  I almost made a new one right away, but I had other work to attend to.  

Which is a strange thing, when you think about it. This is what I do. And yet, that moment of resistance was a quiet reminder that most people are walking around with a headshot that no longer reflects who they are—an outdated hairstyle, a previous role, a different version of their energy.

A past version, still doing present-day work.

And here’s the thing: people notice. Maybe not consciously, but they feel the disconnect between who you are now and who your photo suggests you are. A great headshot closes that gap. It doesn’t just show what you look like—it shows how you show up. Warm. Approachable. Thoughtful. Grounded. Whatever your version of that is.

When it’s right, there’s no hesitation. You send it without a second thought.

I sent mine. It’s fine. It will do its job. But it also quietly told me something I already knew:

It’s time.

If your headshot feels like a past version of you…

Let’s fix that.

I’ve got a studio right here in Maynard, and I’ve built the process to be simple, relaxed, and actually enjoyable (and many clients have said so!). Whether you need one image or a full refresh, we’ll create something that feels like you—right now.

Book a headshot session here

Because you shouldn’t have to hesitate before hitting “send.”