How Often Should You Update Your Professional Headshot? The Complete Guide

Here’s a question I get all the time: “Matthew, how often should I update my headshot?” And honestly, I get why people ask. Professional photography isn’t exactly cheap, and it’s hard to know when your current photo has crossed the line from “still working” to “actually hurting your professional image.”

If someone showed up to meet you and didn’t recognize you from your LinkedIn photo, that’s a problem. If you cringe every time you see your headshot pop up on a Zoom call, that’s also a problem. Your headshot is often what people see before they meet you, and you want it working for you, not against you.

So let’s talk about timing, signs it’s time for an update, and how to make sure your professional image stays current without breaking the bank every year.

The General Rule: Every 2-3 Years

Let’s start with the baseline. Most professionals should update their headshot every 2 to 3 years (actors and models is a different story). That’s the standard recommendation you’ll hear from pretty much any photographer, and it’s based on a simple truth: we all change over time.

Two years might not sound like a lot, but think about how much can shift in that time. Your hair grows. Your style evolves. You age a bit. These are all natural changes, and there’s nothing wrong with any of them. But when your photo is frozen in time from five years ago, it creates a disconnect between how you present yourself online and how you actually look today.

This timeline can vary a bit depending on your age too. If you’re in your 20s or early 30s, you might be changing more quickly than someone in their 50s or 60s. Life events, stress, lifestyle changes, they all show up on our faces. There’s no judgment in that, just reality.

The key is recognition. Your headshot should look like you walk into a room today, not you from three years ago.

7 Signs It’s Definitely Time to Update Your Headshot

Rather than just giving you a timeframe and sending you on your way, I want to give you something more useful: specific signs that it’s time for new photos. Think of these as a diagnostic checklist.

1. Your Appearance Has Changed Significantly

This is the big one. Maybe you grew a beard, shaved a beard, changed your hairstyle, got glasses, lost glasses, or went through any number of other appearance changes. If the person in your headshot doesn’t look like the person in the mirror anymore, it’s time.

I’ve had clients come in who’ve lost weight, changed their hair color, or just aged naturally. All totally normal. But if your headshot shows you with long hair and you’ve had a pixie cut for the past year, that’s creating confusion for people trying to find you at networking events.

2. You Changed Careers or Got a Major Promotion

Career shifts are huge moments, and they often call for a visual refresh. If you moved from a creative role to a C-suite position, your old casual headshot might not convey the authority you need now. If you went from corporate to entrepreneurship, maybe you want something that feels less buttoned-up and more approachable.

Your headshot should match where you are now, not where you were. Think of it as part of stepping into your new role with confidence.

3. Your Industry’s Visual Standards Have Evolved

Professional photography trends change, just like everything else. What looked polished and professional five years ago might look dated today. Remember when everyone was shooting against brick walls? (If you don’t remember, trust me, it was a thing, and it’s thankfully (mostly) behind us now.)

These days, we’re seeing more natural expressions, softer lighting, and backgrounds that add a subtle pop of color or texture without being distracting. If your current headshot has that stiff, overly formal look from the early 2010s, it might be time to update to something that feels more current and authentic.

4. Your Current Photo Is More Than 2-3 Years Old

Even if nothing dramatic has changed, the simple passage of time is reason enough. This goes back to the baseline rule: every 2 to 3 years. Set a reminder if you need to. Mark it in your calendar. Just don’t let it slide to year five or six because you kept meaning to book a session and never got around to it.

5. You’re Launching Something New

Starting a business? Writing a book? Beginning a speaking career? Rolling out a new service? These are all perfect moments to get fresh headshots.

When you’re putting yourself out there in a new way, you want your visual presence to match that energy. New beginnings deserve new photos. Plus, you’ll need updated images for all the marketing materials, websites, and social media that go along with launching something new.

6. Your Hair, Glasses, or Facial Hair Has Changed

I mentioned this earlier, but it’s worth its own callout because it’s so common. Glasses are huge. If you got glasses and your headshot shows you without them (or vice versa), that creates an immediate “wait, is that the same person?” moment.

Same goes for facial hair. If you grew a beard or shaved one off, your headshot needs to reflect that. And hair, oh man, hair changes everything. Color, length, style, they all matter.

7. You Actually Cringe When You See Your Current Photo

This one is less tangible but just as important. If you feel a little jolt of embarrassment or discomfort every time your headshot pops up, that’s your gut telling you something.

Maybe the photo never quite felt like “you.” Maybe it’s technically fine but just doesn’t capture your personality. Maybe you remember feeling awkward during that session and it shows in the image. Whatever the reason, if you don’t feel good about your headshot, it’s not doing its job.

Your professional image should make you feel confident, not self-conscious.

Career Milestones That Demand New Photos

Beyond the general signs, there are specific career moments that really call for updated headshots:

Job searches and career transitions. If you’re actively looking for a new position, you want your most current, polished image out there. Recruiters and hiring managers are absolutely looking at your LinkedIn profile, and your headshot shapes how they perceive you right away.

Promotions and new titles. Moving up in your organization? Celebrate it with photos that match your new level of responsibility and authority.

Business launches. If you’re starting your own company, your headshot becomes part of your brand. You’ll use it everywhere: website, social media, business cards, email signatures, pitch decks, you name it. Make sure it’s working hard for you.

Speaking engagements and conferences. If you’re being introduced as a speaker or panelist, organizers will ask for your headshot. You want to give them something current and professional, not something you’ve been recycling since 2019.

Book releases and media appearances. Authors and thought leaders need strong, current headshots. Period. If you’re being featured in media or on book covers, this isn’t the time to skimp.

The Philadelphia Professional Advantage

Here in Philadelphia, we’ve got a professional scene that’s both polished and approachable. We tend to not be as buttoned-up as say New York, but we’re not as casual as some West Coast cities either. We’ve got our own vibe, and your headshot should reflect that.

I’ve worked with professionals across Philadelphia’s major industries: healthcare, education, finance, tech, creative services, and everything in between. Each industry has its own visual standards, but they all share one thing in common: authenticity matters.

Philadelphia professionals value real connections and genuine interactions. Your headshot should show the real you, the person someone’s going to meet when they walk into your office or grab coffee with you. Not some overly polished, doesn’t-look-like-a-real-person version of you.

Also, a practical note for local folks: think about timing your session for the seasons when you look and feel your best. Philadelphia weather can be intense, so if you’re planning outdoor elements or just want to avoid showing up to a session sweaty from the summer humidity or wind-blown from winter cold, plan accordingly. Spring and fall are beautiful here, and the studio is always a comfortable option year-round.

Making Your Headshot Session Count

When you do book your session, whether it’s with me or another photographer, here’s how to make sure you’re getting the most longevity out of your investment:

Bring multiple outfits. This gives you variety and options. You might find one look works better for LinkedIn while another is perfect for your company website. Having choices means your headshots can serve multiple purposes.

Think about timeless style. I touched on this in my article about what to wear to your headshot session, but it’s worth repeating: avoid trendy pieces that will date your photos quickly. Classic styles last longer.

Get different expressions. Serious, approachable, smiling, thoughtful, get a range. Different contexts call for different energy, and having options means you won’t need to reshoot just because you need a different vibe.

Consider your current and future needs. If you know you’re launching something in six months, mention that to your photographer. We can make sure we’re creating images that will serve both your current needs and what’s coming next.

If you want more details on how to prepare, check out my full guide on how to prepare for your headshot session. It covers everything from wardrobe to mindset.

Don’t Wait Until You Desperately Need It

Here’s a mistake I see people make all the time: they wait until they absolutely, urgently need a headshot before booking a session. Maybe they just got a speaking gig and need a photo by next week. Maybe they’re starting a new job on Monday and just realized their LinkedIn photo is from 2018.

This creates stress for everyone. You’re rushed, you might not have time to prepare properly, and you end up settling for whatever you can get done quickly instead of taking the time to create something you really love.

Instead, be proactive. If you’re approaching that 2-3 year mark, go ahead and book a session before you’re in crisis mode. Think of it like regular maintenance for your professional brand. You wouldn’t wait until your car completely breaks down to get an oil change, right? Same principle.

The Bottom Line

So, how often should you update your professional headshot? At minimum, every 2 to 3 years. But really, the answer is: whenever your current photo stops accurately representing who you are today.

Use the seven signs I outlined as your guide. If you hit on two or more of those, it’s probably time. And if you’re approaching a major career milestone or launching something new, don’t even wait for the signs, just book the session.

Your headshot is one of the hardest-working pieces of your professional toolkit. It shows up on LinkedIn, your company website, conference programs, social media, email signatures, everywhere. Make sure it’s representing the real, current, confident you.

Not sure if your headshot is up to date? Let’s talk. I help Philadelphia professionals create headshots that actually look like them and make them feel confident. We can review your current photos, discuss your goals, and figure out if it’s time for a refresh. No pressure, just honest advice about what will serve you best.