From 2015 to Now: The Headshot Update I Kept Avoiding
Todd Dring
Professional Headshot Photographer and Branding Expert. Founder of The Portrait Parlor Pop-Up.
This week, I finally did something I’ve been putting off for far too long: I updated my headshot. Yes, me, the headshot photographer who is always talking about the importance of keeping your headshot current. For years, I’ve been telling my clients, “Your headshot is often the first impression you make—make it count!” But meanwhile, I was still using a headshot from 2015.
Let’s face it: I had a million excuses. I was busy (aren’t we all?), and I figured my old headshot wasn’t that outdated. But if I’m being honest, the real reason was harder to admit: I was avoiding it because I didn’t like how I’d changed. I’ve aged since 2015 (who hasn’t?), and I’ve gained a few pounds. Updating my headshot felt like confronting those changes head-on, and frankly, I wasn’t in a hurry to do that.
Sound familiar? I hear these same reasons from my clients all the time:
And I get it. Putting yourself in front of the camera can feel vulnerable, even for someone like me who does this for a living. There’s this fear that the camera will amplify every little insecurity you have. But here’s the thing: avoiding it doesn’t make those feelings go away. In fact, it makes them worse.
So what changed? Why did I finally bite the bullet? Because I realized I was doing myself a disservice. My old headshot didn’t represent the person I am today. And while the 2015 version of me was great, I’m proud of who I’ve become since then. Every line on my face, every extra pound—it’s all part of the story of who I am. And isn’t that worth showing off?
When I finally stepped in front of the camera, something amazing happened: I felt a little nervous at first, sure. But as the session went on, I started to relax. I stopped focusing on how I thought I should look and started embracing how I dolook. The result? A headshot that feels authentic, professional, and—dare I say it?—pretty great.
Here’s what I learned in the process, and why updating your headshot is worth it:
And to make this all a little more real, I’ll be sharing both my 2015 headshot and my new one with this article. You’ll see the differences—and maybe even spot the journey I’ve been on. Because ultimately, a headshot isn’t just a photo; it’s a snapshot of who you are right now.
So if you’ve been putting off updating your headshot for all the same reasons I did, let this be your sign. Stop waiting for the “perfect” time, because here’s the truth: the perfect time is now. You’re already amazing just as you are—it’s time your headshot reflected that.
And who knows? You might just have a little fun in the process. I did.