I'm Michele

Do you remember the very first headshot you started using online? Maybe it was for LinkedIn, maybe it was a quick phone photo a co-worker grabbed against a wall in a conference program, or maybe it was cropped from a family photo. And maybe, just maybe you’re still using one of those. (No judgment here — we’ve all been there.)

But here’s the thing: headshots aren’t one-and-done. In today’s world of websites, Zoom meetings, LinkedIn profiles, and social media intros, your photo is often the very first impression someone has of you. And first impressions? They’re made in about three seconds.

So if your current headshot is giving off the wrong impression—or worse, no impression at all—it might be costing you business.

Here are 10 signs it’s time to update your headshot (and maybe even consider a full brand session).

1. Your Background Looks…Well, Dated

Is your headshot against a mottled gray or patterned backdrop that screams “1998”? A dated background doesn’t just age your photo, it ages your business.

Today’s clients want to know you’re modern and up-to-date. A crisp, clean background instantly communicates professionalism.

2. It Doesn’t Actually Look Like You

If your photo is old enough that people do a double-take when meeting you in person, it’s time for an update. A headshot should look like you, today—not the 10-years-younger version. Remember: Authenticity builds trust. If your photo doesn’t match how you look now, it can feel misleading.

3. You’ve Had a Big Change

New hairstyle? Glasses? Facial hair? Significant weight change? If your look has shifted, your headshot should too. Clients should be able to recognize you instantly—whether they’re seeing you online or bumping into you at the local coffee shop.

4. It Was Taken on a Phone

Sorry, but your cropped vacation photo won’t cut it. Even the latest iPhone can’t replace professional lighting, angles, and posing. Your headshot is a business investment—and it shows.

5. It Doesn’t Match Your Brand

Your headshot should reflect not only what you look like, but how you want to be perceived. If your photo feels stiff and corporate but your brand is approachable and creative—or vice versa—it’s sending mixed signals.

6. It’s Inconsistent with the Rest of Your Team

Scroll through your company’s “About Us” page. Do the headshots look cohesive, or like a patchwork of different eras and styles? It might be time to update your headshot (and if you’re a marketing director, consisted updating headshots for the entire team). Consistent headshots instantly elevate your team’s professionalism and make your whole company look polished.

7. It’s Not Aligned with Today’s Marketing

Modern headshots aren’t just “a nice photo of you.” They’re also designed to work across platforms—your website, LinkedIn, social media, speaking engagements, and even marketing cutouts. If your current image isn’t versatile, it’s time for a fresh one.

8. You’re Not Getting the Right First Impression

People will judge your business based on your photo before they ever read your bio. Does your headshot convey confidence, friendliness, and credibility? Or does it say, “This was the best I could do at the time”?

9. It’s Been More Than Two Years

As a rule of thumb, update your headshot every two years—or much sooner if you’re active on social media, networking, or have frequent client-facing roles. A current headshot keeps you recognizable, relatable, and relevant.

10. Your Headshot Was Made With AI

Yes, AI is everywhere right now—even in photography. But here’s the thing: a headshot that isn’t really you doesn’t build trust with clients. People can tell the difference between a polished, professional photo and an AI-generated image. (And even if they can’t, your first in-person meeting will give it away.)

Authenticity matters. Your clients want to connect with a real person, not a digital rendering. A genuine, human-made photo conveys confidence, relatability, and trust in a way an algorithm simply can’t.

So by all means, use AI for streamlining your business, but leave the photography to an actual camera.

Bonus: Don’t Stop at Just a Headshot

Headshots are the handshake, but brand photography is the full conversation. A library of brand images (showing you at work, lifestyle photos, team interactions, details, etc.) gives you content to market authentically—day after day.

Ready for Your Update?

I’ve photographed thousands of headshots and brand sessions here in Rapid City, South Dakota (and beyond). Whether you’re an entrepreneur, realtor, attorney, or creative professional, I’ll help you create a headshot that feels natural, professional, and completely “you.”

✨ Ready for your update? Book your session with Michele with one L Photography.