Is your headshot as old as mine? (And is it on your website?)

I realized the importance of accurate headshots years ago at a conference when someone I worked with closely didn’t recognize me (at all!) from my picture. This was probably because my headshot was 6 years old at the time.

These days, with Zoom, it’s even more important for me to have photos on my website that actually look like me … so when I show up on Zoom, they don’t say, Who’s that?! Even though the last time I redid my headshots seems like yesterday, it was 2014. Things have changed since then. My hair. My glasses. The 7-years-more-experience look in my eyes. :) 

Getting over it

I know it’s hard to get a new photo — especially when you think you look better in your old one. All of my personal hesitations got in the way, and before I knew it—my 2008 picture looked nothing like 2014 Jill. Then, my 2014 picture didn’t look very much like 2021 Jill and so on…

Sure, it’s a journey. It took me getting over myself and my insecurities. But at the end of the day, I want to be myself. I want to be real (in the same way that I recommend authentic images on your website).

You’re beautiful. You don’t look like you did 7 years ago. And that’s perfectly okay. Time goes on, your face changes, and having an old headshot is pretty much like smacking your current self in the face. So mean. If you’re a creative person, it’s likely you’re married to aesthetics and visuals. All the more reason your photo needs to be accurate. And, if you don’t have your photo on your site, you really should. It’s a great way to add personality to your website. Sold? Good. It’s time to get new headshots.

Here’s my headshot evolution…

2008 headshot
Jill Anderson
2014 headshot
Jill Anderson
2021 headshot
Jill Anderson WordPress Designer
2023 headshot

A few more pics from the photoshoot…

8 headshot tips for a photo that’s really you

  1. Put yourself in good hands. My photographer neighbor made it easy. When she started her business in 2014, she needed a logo, and she came to me. I said, “I need headshots—let’s barter!” In 2021, I hired professional photographer Teryl Jackson of Teryl Jackson Photography. I definitely recommend a professional who knows about lighting, angles and editing in a way that you probably don’t. And even if you do, it can be hard to see past ourselves, especially when it comes to putting ourselves out there.
  2. Have a conversation. If you’ve found a great photographer, they’re going to have a process to help you. Hopefully this process includes a conversation. Mine got to know me and my concerns, like and dislikes.
  3. What to wear? I ended up super casual because that’s what I’m comfortable in. That’s my style. Stick to your style—you don’t have to be dressed formally. It’s important that you look and feel natural, not stiff or contrived.
  4. Get your hair and makeup done! I’m all about being myself and owning what I look like — but there’s nothing wrong with a slightly polished version. A little hair and makeup help will make you feel more comfortable in front of the camera and send across some of those confidence vibes. 
  5. Colors. There are a few things to consider here. 1) Think about where your picture will be on your website. It should go with your color scheme, not clash. 2) Be careful of wild patterns, especially if they take away from your face. It’s fine in fashion, but not in your headshot. 3) Wear a color that suits your skin tone and doesn’t wash you out. Your photographer can help you make these choices.
  6. Location. I love my office. I knew I’d feel most comfortable here. And since I’m behind my computer every day—my location was an easy choice.
  7. Go ahead—be trendy. Trends can be cool, and they can show that you’re current. Since your picture shouldn’t be more than two years old (just like your website should be current!), go ahead—use desaturation, yellowing, or whatever trend moves you.
  8. Find inspiration. Spend some time online looking at headshots of people you admire. In the same way you’d approach a design project, this will give you inspiration and something to show the photographer.

You love what you do, right? So do I. Do your business proud by showing yourself off.

If your new headshot needs the perfect website, I’d love to help.

About Jill Anderson

Hi, I’m Jill, a WordPress WordPress designer/developer who partners with talented designers, copywriters, and agencies on their websites, and their client’s sites. I’m passionate about crafting beautiful and innovative WordPress websites focused on clear positioning and positive user experiences. Get my free report, Get Your Website Done: 12 Actionable Steps for Designers, and check out my Client Onboarding Toolkit, a simple 4-step digital course for converting prospects into a paying clients.


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6 thoughts on “Is your headshot as old as mine? (And is it on your website?)

  1. Great article! I buckled to peer pressure last year and also got a professional headshot, and so glad I did. It’s hands’ above better than the grainy picture I’d been using before.

    But you got me at the photo in a circle bit. That’s exactly how I styled my photo, but I did it because I thought it looked modern and different. Who knew that it was an actual trend?! Awesome. Look forward to meeting you at CFBC in Boston!

  2. Thanks Jill – this is something I’ve been meaning to do as well. My headshot is at least 20 years old now. I had a pro photographer do a series of photos way back when.

    Of course, now I’m older, heavier and I’ve never been photogenic either. Well, the pro photographer I worked with did miracles…I looked like a model. Having a pro makeup artist for photo day also made a huge difference…for both color and black and white images.

    For my next image update, I’d like to take some goofy shots along with more stylish ones to mix it up on my site. I think for me, being outside has been the most successful in looking my natural self.

    Thanks for the tips on getting good images too. All good info!

  3. My headshot photographer insisted on a pro makeup artist at the shoot. And wow, it made such a difference. I never put on much makeup but she piled it on and made look amazing and yet somehow still me.

    I suddenly saw the resemblance between me and my cousins (that I had always looked up to as a child) so what was a business event ended up feeling like a emotional, personal journey. I actually wanted to cry except it would have ruined all her work!

    1. Yeah, the last time I had a makeup artist do my makeup was at my cousin’s wedding, gosh, 6 or 7 years ago. Made me feel so pretty :)

  4. @Sonia Yes, I think Google+ started the photos in circles rage. Now it seems like they’re everywhere—and I love it :)

    @Sherri oooohh, pro makeup artist. I’m gonna do that next time. Great idea!

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