A little over five years ago, I got into recovery in AA. So a lot of chaos before that and a lot of figuring things out. Because of that, professionally, I really didn’t have direction. I had done sales, I had done restaurant work, a bunch of stuff. About a few months in, I made the decision to do something different and I actually picked up a camera and I discovered that I liked it and enjoyed it. I wasn’t good at the time, but I liked it and enjoyed it.
And then, about three or four years ago, I saw some YouTube videos on a guy named Peter Hurley in New York, who’s phenomenal. It was a different time when he got into headshots so he was able to just put ads in the newspaper and build his business from there. He’s also in Manhattan, so I’m sure that helps – there are more people, there’s more of a market. But I was hooked. I saw just in the way he talked about it, in the way that he believed in what he was doing, that it was more than just photography. It was a way to highlight somebody’s best self.
How to Build Rapport and Succeed as a Headshot Photographer:
Inspiration and Influence in Headshot Photography
Still to the day, my favorite people are the people who are like, “I’ve never had a good picture. I look terrible. I’m unphotogenic.” And then when you get them an amazing picture, it’s like you can see the confidence building up in them, and that’s one of the many reasons that I love doing it.
When I have somebody in front of my camera or even a team of people, just seeing the transformation and getting to help people, sometimes, honestly, sometimes, depending on the session, it can be more like a therapy session. Especially in an individual. Maybe not in a team environment, but in an individual session. It’s like we have a little more time. It’s a little more intimate. And I’ve had people share losses they’ve had in their lives, and I get a little emotional. I get to actually be there for people. To help people and be a part of their journey.
Transition to Full-time Headshot Photography: A Shift Towards Corporate Focus
Last year it was my first year doing headshot photography full-time. I did a little bit of school photography to kind of help with the bills, but my family situation changed and the bottom line is my wife and I couldn’t both be working at that time. Even though it was a little bit of a mix of individual sessions and team, and I enjoy both, I’m now focusing on more of the corporate side, just from a business perspective.
I can do 10 clients individually, which is a lot more work, and I enjoy it just as much, or I can have one or two days of shooting and make the same amount. So I still am doing individuals and would like to continue that but for sustainability and making the business side of things work, I’m focusing on corporate. And I’ve gotten tips from other people that have been in the business longer than me and they say sometimes you’ve got to sacrifice and do the things that are going to enable you to do the other things you want.
I had one client, a corporate client whose CEO was kind of a little dry, to be honest, but other than that, working with teams is great, too. I’ve had people who are very appreciative and we have a lot of fun. Lots of laughs and stuff like that. And, at least so far, I’ve not had anybody that was difficult, I’ve had all great people, great teams – I’ve been fortunate in that regard.
Benefits of Headshot Photography
Now that I’m at a point where the business side is really coming into the picture, I’m working hard on the marketing and business side of things. So, my advice to anyone trying to do this as a profession is to know that it’s not instant. At least in my journey, it hasn’t been an instantaneous thing. Albeit five years ago, I had barely even touched a camera, so maybe that played a role in it.
I’d say for me personally, one of the biggest selling points of headshot photography is the people aspect of it. There’s the technical and the lighting and all that sort of stuff and I’m focused on trying to branch out into more branding stuff and more creative type shoots, but just the people side of things. I get to go and be a part of somebody’s journey and have them trust me to make them look their absolute best for their first impression.
Nowadays, that’s the first thing people see when they look you up. They look you up on Google, they look up your Facebook or your LinkedIn and that headshot is right there. And just seeing people’s confidence transform, their gratitude for it, and just getting to interact with people whether it’s in a team environment or one-on-one, you get to hear their stories and what they’ve been through, what they’re doing, where they’re going, and for me, that’s the biggest thing. That’s what I love about it.
Storytelling Through Portraits
I think one of the keys, and I learned this from some mentors, but I’ve also seen it in my personal experience, is that when I meet somebody or they’re interested or even when we meet face to face for their session, the lighting, the camera, what they’re wearing, any of that stuff, that’s not what we talk about first.
It’s a human interaction first. I’m asking questions. At the same time, I might be in my head, looking at their face and gauging what angles we’re going to do, what they look like, how tall they are, all that sort of technical stuff. But we’re talking as humans trying to have a conversation, build that rapport. Then, honestly, I feel like it’s based on the individual that’s the subject that I’m with at that time. It’s just gauging where they’re at emotionally, mentally, even physiologically. Are they nervous? Are they relaxed? Are they more of an outgoing person? Are they a little bit shy? I use my intuition to kind of gauge where they’re at because there are people that love taking the pictures and then there are people that are extremely shy and just want to get it over with.
I feel like that’s an important factor that you only really get when you’re in the moment with the person. It’s about staying in the moment too, and just being present for them. Which is not always easy because we all have a million things going on in our lives and to separate that and walk into the session and be like, okay, all that stress, all the things that I’ve got going on in my head, I’m going to leave that there. I’m with this person now.
I don’t do it perfectly at all, but that’s the goal, at least. To be able to walk in and just be present and available for them in whatever way they need. I’ve had clients that were dealing with the loss of a spouse, losing a job, all sorts of stuff like that. And then there are clients who are 70 years old and never had a good picture in their lives. Everybody’s different. Everybody’s come into it with a different attitude and a different story behind them.
Building Rapport and Easing Nervousness: The Art of Authenticity and Humor
When it comes to making people feel comfortable, I’ll share a little bit about things that I do. Humor is a big one. But you’ve got to gauge each person and each situation. Again, back to being present and knowing who you’re dealing with, if I’m dealing with a CEO versus somebody who’s in human resources, I might tailor it a little bit differently, but I’m still going to be myself.
Just be who you are. Because people see that authenticity and they feel it, and that’s going to make a difference. I’ve had a few clients where I could tell that I’m just a different type of person than they were, and that’s fine. We can still get the session done and have them feel comfortable, but just recognizing that, ultimately, my goal is to be authentic and to be myself. First and foremost.
Back to humor. Humor is a big thing, whether it’s being silly, whether it’s having some one-liners. One thing I’ve learned from other people, and I’ve also implemented it in school photography, and now, especially in headshots, is saying things that snap people’s brains out of it, that are kind of out of the ordinary. This is a big tool for building rapport, especially when we’re starting to get into the session.
One of my go-to one-liners is, “Can you just unscrew your left ear a little bit?” It’s just so random. When people are nervous and they’re thinking things like, “What do I look like?” and “How’s my hair?” or this and that, sometimes it confuses them, but then they burst out laughing. It tricks their brain almost; they’re so confused by it or taken aback that it snaps their brain out of the chatter that’s going on. So that’s a big trick. Be yourself but if you have random things or things that are just going to totally take them where they didn’t think they were going, use them. I’ve seen other photographers do it, and I do it myself, and it definitely helps snap people out of that nervousness and make them feel more comfortable.
It’s a balance though. I am all about being myself and trying to have fun and be comfortable, but ultimately it’s just a back and forth of give and take, of seeing where that person’s at individually. And then tailoring it to that specific individual.
Again, the first thing I’m doing before we even get into the session itself, where I might be doing those sorts of things, is having a conversation with them. I don’t think about it consciously, but just through people’s body language and how they converse with me, I’m able to pick up on things. Is this person from a privileged background where throwing some crazy jokes out there might be a little offensive to them? Or is it somebody more down to earth? It’s about getting to know somebody’s personality and understanding where they’re at and then being able to tailor what I’m doing. You want to be appropriate at the same time.
A Continuing Journey of Connection and Transformation
Each and every person I encounter has a story. They’re completely unique and in my opinion, exceptional in their own right. Capturing that, authentically and in the best light (pun fully intended), is the goal of my headshot adventures. From my roots in AA recovery, through a late-life introduction to my headshot passions from influencers like Peter Hurley, this slightly unconventional path has taught me exactly how powerful headshots are in each subject’s path.
The transition of turning my headshot photography passion into my full-time income and business has come with its own set of challenges and rewards. Balancing the intimacy of individual sessions, the dynamics of team headshots, and even the business aspects, I’ve witnessed the many diverse stories that bring people in front of my lens. Even the business side has opened my eyes –attending to each person’s unique tale and needs.
As I navigate the intricacies of each session and the humans I am collaborating with, I find that authenticity and humor become invaluable tools in easing nervousness and creating a comfortable environment for my clients. Along with the technical photographic proficiency, connecting with each human is equally essential.
As my personal journey continues to unfold, each click of the camera marks another chapter in the ever-evolving narrative of both myself and each human who entrusts me to capture their essence. As I strive (key word) to be more present and authentic, I look forward to the countless stories yet to be told and visually captured through the lens of headshot photography.