When I decided to launch my own business, there was one task I dreaded the most and postponed the longest: My headshot.
Sure, I had to have a headshot — it’s critical for anyone doing business these days. But I fear having my photo taken the way some people fear spiders, cilantro, or doing math without a calculator. So, I needed to find a photographer I could trust to help me look my best: polished, professional and without that strained expression I always wear when someone points a camera at me.
When the time came that I could procrastinate no longer, a business contact told me about Stacy Kaat. “You’ll love her,” she said. I braced myself and decided to give Stacy a call.
I’m glad I did. From our first conversation to the moment we were reviewing final images in her studio, Stacy put me at ease with her cheery energy and friendly professionalism. What started as a dreaded necessity ended with photos I actually like. “I really enjoyed my time at your studio,” I told Stacy when we were done. “I never thought I’d say that about getting my photo taken.”
Here’s how she did it.
Laying the groundwork
Stacy started by asking about me about myself and my goals. I explained what kind of work I do, saying I needed a headshot for my social media accounts, professional email account, and miscellaneous business profiles. I also told her how much I hate having my photo taken.
She was undaunted. She assured me that she works with plenty of camera-shy people and takes pride in making them feel comfortable. I liked that Stacy once worked as a hair stylist — she would have an eye for what complements my face and could get my bangs to behave, too. Bonus!
I booked an appointment by using a form on her website that asked for basic information, a payment, and an email address.
Preparing for the big day
In the days after booking, I received a helpful series of emails from Stacy about how to find her photo studio (it’s in Milwaukee’s Bayview neighborhood) and prepare for my headshot session. I appreciated her advice about what to wear and how to choose accessories. One tidbit: Avoid white shirts buttoned all the way up because the white reflects under your chin, diminishing your jawline. Who knew?
The emails also encouraged me to be well-hydrated and well-rested on the day of the shoot. I was reminded to bring my makeup along for touch-ups. And I made sure not to overbook my day — arriving flustered would make it hard to relax.
I called Stacy to ask her opinion about my wardrobe ideas (we decided I’d bring several options). We also discussed whether to book a makeup artist but, because I like a natural look and because Stacy can do touch-ups in the photo-editing process, I decided to handle my own makeup.
My headshot session: Getting started
As encouraging as Stacy was, I did not exactly skip my way to her photo studio on the day of the shoot. She’d have her work cut out for her.
Stacy’s studio is tucked behind a house in a quiet residential neighborhood (easy parking, by the way). When I knocked on the door, Stacy greeted me warmly and immediately started putting me at ease.
Her studio is charming and functional, with a roomy bathroom to change in, a well-lighted mirror for makeup and a comfy seating area. Filling most of the space was the area where I’d pose for the camera — a backdrop flanked by lighting and photography equipment.
Stacy was encouraging as we discussed what I was aiming for and what wardrobe choices might work best. I wanted a headshot that wasn’t too conservative or too casual, but somewhere in the middle (no problem, Stacy said). I was torn between my go-to black tunic and my coral-pink blouse (let’s start with the pink, we decided).
Once I cleaned my eyeglasses, touched up my makeup, and decided on a throwback-pop playlist, we were ready.
The next 30 minutes or so were filled with laughter, chitchat, and lots of prompts to lower my chin, stick my chin out, move my body position, show some teeth.
We started with test shots, which Stacy used to make small adjustments and position the lighting equipment. She explained that she needed to find the ideal lighting for my facial structure and to make sure my eyeglasses would not show glare. And, just as I was hoping, she worked a little magic with some hairspray to give my hair lift while still looking natural.
I was awkward at first. I quietly grumbled when Stacy asked me to dance in place and loosen up a bit. But letting myself be a little goofy actually worked, and as the session went on I became less and less self-conscious.
Even though my headshot would only show my head and shoulders, Stacy understood that my entire body position made a difference. We tried shoulders square to camera and angled, standing straight and with a one foot on a small bench, hands on hip and one hand in pocket. She suggested small adjustments and often paused to smooth a wrinkle or adjust a seam. We switched from a necklace to a scarf. We decided not to bother with the black top.
Seeing (and sorting) the results
We stopped shooting after about 30 minutes, at which point I chilled while Stacy sat at her computer to cull 150+ images to about 30. Every shoot is different, she explained, but this amount is about average. Then we sat together for a quick review of the 30 images, which went something like this:
Me: “Yes. No. No. Maybe. Yes but one eye is squinty.”
Stacy: “I can fix that.”
We also burst into giggles at times when my face was clearly not cooperating — including the moment when I grumbled over doing that dance. These wouldn’t make the cut, but they gave us a good laugh.
We narrowed our choices to about 20 images, which we reviewed again. I was amazed at the difference that bit of hairspray made early in the shoot. I liked some of the more confident, serious looks but wondered if they’d be “friendly” enough for social media. I debated between necklace and scarf. In the end, I decided on three images, figuring that a little variety would be nice.
As a last step, we looked at the final three even more closely and discussed touch-ups I might want — whiter teeth, for instance, one dimple that didn’t look right to me, and open that eye a little.
It wasn’t so bad after all!
The fact that I am not describing all this as torture is a testament to Stacy’s bubbly, encouraging style. During the photo shoot, her congenial conversation starters distracted me from self-conscious worries. She offered lots of positive prompts. She paused occasionally to show me how the photos were looking and get my feedback.
It was never about doing things right or wrong — just giving it a go. Stacy made it a fun, collaborative process. It was clear she wanted me to be happy with the results, and I was.
Am I completely over my fear of being photographed? Nope. Unless, that is, Stacy is behind the camera.
Live Out Loud with Stacy Kaat
Business & Personal Brand Photography