AI Professional Headshots Offer Self-Esteem, Comedic Relief

• A TikTok featuring an AI service promising studio-quality headshots for $17 intrigued me.
• Some of my results were a self-esteem boost, while others were comically awful. 
• All in all, I came away with two usable pictures, which I consider a win.

Of all the tedious administrative tasks related to job searching — and there are many — getting headshots taken has to be near the top of the list. 

Professional headshots can get expensive, and they’re not something that many working stiffs, or non-celebrities, are moved to spend much time or money on.

But the photos do need to look good. LinkedIn, after all, is where many prospective recruiters, customers, and employers first lay eyes on you. At the risk of sounding lookist, your picture matters. 

So when I saw this TikTok about an AI service that promises low-cost, studio-quality headshots, I was intrigued. Some of the pictures were terrible — extra hands! sausage fingers! dead eyes! — but there were plenty of winners, too. It was worth a shot.

Because when all is said and done, I’m just a mildly vain, 40-something working mom who wants to look halfway decent on LinkedIn. 

Well, dear reader, I got my wish and then some. Some pictures offered a jolt of aspirational self-esteem, as in, “Wow, I kinda sorta look like that? Cool!” While others were comically awful or just plain hilarious.

Professional headshots from the comfort of home

I used Try it on.ai, which gets points for user-friendliness. You create an online account, pay $17, and then upload at least 10 pictures of yourself, though the platform says that more pics are preferable — and voilà! A mere 72 hours later, you get 100 headshots.

Choosing the pictures to upload was deceptively time-consuming. Then again, getting dolled up and traveling to and from a studio would take hours. Sitting on my couch and scrolling through my phone’s photo library wasn’t too bad, all things being equal.

The site recommends uploading close-ups taken from the chest up. You can’t be wearing a hat or sunglasses, and if you submit blurry, pixelated photos, or ones taken from awkward angles, it will affect your results.

I selected my pictures carefully. The perfect headshot, in my mind, is one that conveys a serious person who doesn’t take herself too seriously. I wanted to look diligent and hardworking, the kind of journalist who hits her deadlines — but who’s also capable of passing the airport test. 

There were other considerations, too. Ageism in the workplace is a big problem and something that any middle-aged worker — or, frankly, anyone over 35 — needs to be mindful of. I wasn’t looking for a headshot to make me look younger per se, but I didn’t want it to prematurely age me either.  

Research suggests women also face extra challenges. Ideally, I wanted my headshot to convey personal warmth. And while it’s advisable to look attractive, you shouldn’t look too attractive. The feminist in me is loath to kowtow, but the realist in me is practical. 

This is all to say, I didn’t have a ton of great uploadable options at my disposal. 

But, my friends, it didn’t matter at all.

Glamour, professionalism, and Michelle Obama arms

My results were at turns pleasing, horrifying, and downright ridiculous. It’s a kick to see photographs of people who look me-ish wearing clothes I don’t own and making facial expressions I don’t make.

Without further ado, here are some of the greatest hits, along with a smattering of commentary:

This one cracked me up the most. The stark, black turtleneck was first popularized by the late Apple cofounder Steve Jobs. The look was later adopted by Elizabeth Holmes, the disgraced founder of Theranos, the blood-testing company, and according to the New York Times, became a symbol of fraud. Not a smart choice for a headshot.

The glamour quotient of this one also amused me. I feel like it would make a good headshot if ABC was considering a reboot of the TV show “Cougar Town,” but it lacks a certain professionalism. Also, get a load of my Michelle Obama arms.

While I appreciate my chiseled cheekbones and I dig those funky earrings, this picture looks nothing like me.

Ditto this one. I also question the subtle come-hither expression on my face. But I like that coat.

This one takes the cake. This is what I could look like a couple of decades from now, when my hands have grown in.

These two above actually do look a lot like me. My husband, who sees my face more than I do, agreed.

OK. Maybe they look like me on my best days.

All in all, I got two usable pictures — ones that look enough like me — to make the $17 worthwhile. And for the ones that didn’t make the cut, well, the comic relief was a gift.