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AI-Barbara v2

I Tried AI Headshots. Here’s What You Need to Know.

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“Congratulations! You’ve been accepted to this program. It starts on Monday. Please upload your current headshot in the next 48 hours.”

Gulp.

Brief elation of getting into the program quickly gave way to anxiety. My last professional portrait was from February 2020 – a lifetime ago in both personal and global terms. I certainly don’t feel like the same person I was five years ago. And I certainly don’t look like her anymore, either. But with no time for a traditional photoshoot, I faced a quagmire: should I use an outdated photo or explore AI-generated headshots?

The Dilemma of Digital Self-Representation

A headshot isn’t just a photo; it’s often the first impression we make in professional contexts. As I stared at my outdated blonde portrait (I’m now back to my natural raven-hued roots), I wondered: How much does authenticity matter in digital-first impressions? Don’t many of us automatically expect some airbrushing? And who among us doesn’t use the Zoom filter to blur our dull skin?

My thoughts also turned to authors looking for professional headshots for their dustjackets. What if AI headshots were the only affordable option?

What does it mean to be “authentic” in an age of filters, touch-ups, and now, AI generated portraits?

Exploring the AI Headshot Marketplace

I didn’t have time to dwell on such deep questions and pushed them out of my mind. After frantically scouring the internet for a reputable site, I landed on InstaHeadshots, which promised “Stunning headshots for busy professionals.” Well, that’s me!

Most sites offer roughly the same base rate of $40 or so per package, so I wasn’t ranking on price. I wanted a reputable site that wouldn’t traffic in my personal data beyond what I wanted it to do: generate a headshot using only my images.

The process looked simple enough: upload ten photos, pay $39, and receive 40 AI-generated headshots in less than an hour.

I’ve been using this headshot since February 2020. I think there’s a warmth in this shot that the digital renderings can’t replicate. (credit: Jane Goodrich)

Babs in her bottle blonde phase. (credit: Nick Basbanes)

But as I hovered over the “submit” button, nagging ethical questions kept percolating. What’s going to happen to my personal photos? How is the AI trained? Am I helping normalize AI-generated images in professional settings?

The FAQ from InstaHeadshots provided some reassurance: photos are deleted after 30 days, and the AI only trains on the images I provide. Reasonable enough, but with massive data breaches becoming as common as a winter cold, I had misgivings about whether I could completely trust any company with my digital life. InstaHeadshots offered no answers for those queries.

The Results: Valley of the Dolls Meets Corporate Headshot

But for $40 bucks I could be a sport. I made my selections and set the algorithm in motion. Thirty minutes later, I was staring at 40 AI interpretations of me.

The results were unsettling.

I saw someone who looked a lot like me, like a wax figure at Madame Tussaud’s. The InstaHeadshots algorithm seemed to be working overtime to ensure that its portraits didn’t look completely airbrushed. I noticed that many sample portraits on the website carefully highlight human “imperfections” like crow’s feet and light forehead wrinkles. In one most of the portraits I commissioned, AI added some creasing around my eyes while removing the fat bags under them! Between that, the subtle face-slimming and the neck-lengthening, I simultaneously look older and younger.

Here’s one that completely missed the mark:

Paging Demi Lovato! This gal is stunning, but she is definitely not me. She’s wearing a TON of makeup and her skin texture looks like clay. The nose, the hairline, the sculpted brows—it’s not my face. Scrolling through the rest of the images, I noticed the AI favored a natural look: subtle eye makeup and a neutral lip tint. Default professional vibes? Sure. But what if I wanted red lipstick? Or blue eyeshadow? Currently, there’s no way to change makeup, but if I typically wore a full face of makeup, a toned-down look might seem inauthentic.

I think, if I had to choose a portrait, this is the one that looks the most like me:

And yet…it’s still not me. The right eye on AI-Babs is smaller than the left, and she looks a little vacant. I wish my hair and makeup could look this good. And that swanlike neck! She makes my 2020 portrait look like I’m a hunchback by comparison. I hemmed and hawed until I decided that this was the one I was going to upload to the program website.

I got cold feet. I thought to myself, This isn’t me! This is an algorithm’s approximation of what I might look like. Convenience was bumping up against authenticity, creating a wedge between embracing cutting-edge technology and my desire to hold onto something fundamentally human.

I began to question the implications of using this image as my digital doppelganger, my AI-sosie. If I submitted it, would I be misrepresenting myself? The AI smoothed out my skin, perfected the lighting, and endowed me with that Mona Lisa smile. But it had also erased the imperfections and quirks that make me, well, me. The warmth and spark of the authentic portraits was missing, too.

Moreover, I wondered about the message I’d be sending if I used an AI headshot. There’s already so much pressure to present a polished, perfect image in the workplace. Would I be contributing to an unrealistic standard, making it harder to share our authentic selves?

If AI headshots become commonplace, what does that mean for professional photography? (The jury’s still out: some critics say AI is heralding the end of professional photography, others suggest embracing AI, and still others swear that AI will never replace a human behind a camera. What about the subtle (and not-so subtle) biases baked into AI systems perpetuating specific beauty standards?

Babs, you’re overthinking this. Just upload the pic and move on already.

I couldn’t do it.

I chose authenticity over AI perfection. Blonde Babs would have to do.

It felt like a small stand for the value of human imperfection in a world of digital flawlessness.

But, believe it or not, I wasn’t sure I made the right decision.

The Aftermath and Reflections

In the week that followed, I was still haunted by the experience. In a moment of curiosity (or perhaps digital masochism), I updated some of my social media profiles with one of the InstaHeadshots images.

I wondered what the response would be. Well, it’s been…radio silence. No one seemed to notice–or care–that my profile picture was now an approximation of myself, except in cases where I mentioned that the profile picture was AI-generated. This lack of reaction was, in its own way, more unsettling than any criticism might have been. Are we already so accustomed to curated, perfected images that an AI-generated one doesn’t raise an eyebrow?

Don’t Take My Kodachrome Away?

I’ve left the AI-generated headshot on some of my social media profiles and gone back to the bottle blonde for others. Sure, it’s inconsistent, but I’m not ready to completely go digital in my physical representation.

For authors who are deciding whether to try an AI headshot session to get some quick dustjacket portraits, I would say that if you have an extra $40 and are willing to see your face transformed in a digital blender, go for it. But don’t fogo a photo; all authors really should invest in a professional headshot. And if you do decide to hire a photographer, the great publishing-industry guru Jane Friedman offers ideas here on what to look for in a great session. (Good advice never goes out of style: this story was originally published in 2009!)

As for myself, the experience has been illuminating, but I’m still back where I started–no current headshots of the real me. But maybe there’s hope: I just bought my daughter a Kodak Pixpro point-and-shoot, which she’s been begging for for the past two months. Apparently, “vintage” (we’re talking twenty years here) point-and shoot digital cameras are having a moment among Gen Zers, who are looking for more authenticity in their heretofore carefully curated image-centric lives. “I just want pictures that look real,” my daughter said to me. She really wanted a no-name Chinese fake from Amazon, but I couldn’t do it. Sorry, kid, Kodak will have to do.

What do you think? Have you tried AI headshots? How are you navigating the balance between putting your best (digital) face forward while maintaining authenticity? I’d love to hear your experiences in the comments below.

Author Barabara Basbanes Richter, Founder of DIYBook
About the Author

Barbara Basbanes Richter founded DIYBook, an affordable and easy-to-use book writing program. She also founded In Ink Ghostwriting, a full-service ghostwriting firm helping politicians, pundits, scientists, CEOs, professional athletes, and others get their stories into print.

Under her own byline, Barbara’s writing has appeared in The Wall Street Journal, The New York Daily News, The Vineyard Gazette, Humanities, The Sewanee Review, Fine Books & Collections, Literary Features Syndicate, High Country News, Ravishly.com, Westchester Magazine, and other outlets.

Barbara is a fluent French speaker, and her translation from French to English of Mademoiselle de Malepeire was called a “clever, inspiring gem.”

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