What a Boston Headshot Session Is Really Like (And Why You Should Like Your Photographer)
There's a question almost nobody asks before booking a headshot. They'll ask about price, location, turnaround time, and whether hair and makeup is included. All good questions.
But here's the one that actually predicts whether you'll love your photos: do you like the person taking them?
I know that sounds soft for a business decision. It isn't. A headshot is one of the most vulnerable things you'll do for your career. You're standing in front of a stranger, a little self-conscious, hoping the result looks like the best version of you. In that moment, the relationship between you and your photographer isn't a nice-to-have. It's the whole ballgame.
A great Boston headshot session isn't a transaction you survive. It's a couple of hours you actually enjoy with someone who gets you.
Why "Anyone Can Take a Photo" Misses the Point
A camera is a camera. Lighting is lighting. On paper, a lot of people can take a technically correct photo of your face.
But that's not what you're really buying. You're choosing someone to be in the room with you during a moment that asks you to be open. You're trusting them with how the world is going to see you. And the truth is, people choose photographers whose values match their own, because this is far more than a service anyone can provide.
When the fit is right, you can feel it in the photos. The person looking back at you from the frame isn't performing. They're at ease, because they were with someone they trusted.
"I had a great time with Kevin for my professional headshots! He is very engaging and made me feel like I was joking and chatting with a good friend, even though I'd only just met him." — Norelle Done, Google Review
When Your Photographer Gets You, the Walls Come Down
Nate James Bae Kupel wrote something after his session that I think about often. [LINK]
He shared that growing up, he didn't see many people who looked like him, and that he often struggled to even feel comfortable looking at himself in the mirror. Posing for photos never came naturally to him.
What he said next is the entire reason I do this work. He said I have a way of breaking down the walls we put up around ourselves, to bring harmony between how the world sees us and how we see ourselves. I did force him to pose for photos between bad dad jokes, conversations about politics, and trading stories about parenting our kids.
While others try to break down those walls with their expensive equipment, find a headshot photographer to break them down by being a real person, sharing a few laughs, and caring about the human in front of you.
The Best Headshot Sessions Don't Feel Like Work
Parker Chase-Corwin came by the studio with his colleague Mike, and the way he described the morning afterward still makes me smile. [LINK]
He called it a guilt-free morning to have a surprise photo shoot with a friend. Not a typical way to spend a work day, he said, but he and Mike got to visit Three Circles Studio and goof around for a few hours, taking their brains out of the grind and doing something totally different.
His words: "Good for the soul."
Nobody describes a transaction that way. You don't say a trip to a vending machine was good for the soul. That phrase only shows up when the experience itself meant something. And the results were great too, which is exactly the point. When the session is fun and human, the photos follow.
"I actually had a blast during the session because Kevin made it so fun! We connected on all things higher education, purpose, and work culture." — Stephanie Khumalo, Google Review
Why I Photograph the Same People Again and Again
Yawa Degboe said something that genuinely moved me. She wrote that her most authentic professional relationship may be the one she has with me and my team. [LINK]
There's no hiding your feelings in front of a camera, she said. Over the last few years, I've documented her professional growth one headshot at a time, and in doing so she's watched me bring my vision for Three Circles Studio to life.
That's what happens when a headshot stops being a one-time errand and becomes a relationship. People come back, not just because the photos are good, but because the experience is built on trust that deepens over time. I get to watch people grow, and they get to be seen by someone who actually knows them.
The Photo People Recognize Instantly
When I photographed Michele Courton Brown and shared her portrait, something beautiful happened in the comments. [LINK]
Her community showed up in force. Person after person called her an inspirational leader and a mentor, and the affection was impossible to miss. These were people who clearly adore her, and they recognized her real self in the photo immediately.
Michele responded too, thanking me and noting how glad she was to champion my growth. That's the part that tells the whole story. The respect ran in both directions. We share a belief in community, in lifting people up, in making people feel seen. When your photographer shares those values, the work carries them. You can't fake that kind of warmth, and you can't manufacture a room full of people who recognize someone they love.
"Kevin genuinely connects with clients and helps them have fun and shine." — Shelley Reese, Google Review
How to Find a Headshot Photographer You'll Actually Like
So how do you find a Boston headshot photographer you'll actually like? Look past the gear lists and the price sheets. Read how past clients describe the experience, not just the results. Notice whether people talk about the photographer as a person. See if their values line up with yours.
When you get that fit right, the headshot almost takes care of itself. You show up, you have a genuinely good time, and the camera catches a real version of you because you felt comfortable being it.
That's the kind of experience I've built at Three Circles Studio. If you want headshots that feel like you, taken by someone who actually enjoys getting to know the people in front of his camera, I'd love to meet you.
Book a headshot session at Three Circles Studio in Malden, just outside Boston. Come find out what a session that's good for the soul feels like.
Three Circles Studio is a Boston headshot and event photography studio located at 75 Pleasant Street in Malden, MA. With 600+ five-star reviews, we're one of the top-rated headshot photographers in Greater Boston.
