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Five Adjectives Describing Carolyn: Discerning. Decisive. Intuitive. Rigorously Honest.

A couple years ago, I asked my client, Carolyn, if she would share some thoughts on her experience from working together. We had had so many great conversations that lasted hours over the course of getting to know each other, I always enjoyed talking to her and laughing, a lot, together. So we sat down over zoom for an interview.

KK:. What was the number one reason you wanted to do the photo shoot?

CMD: Previously, I just sort of got a head shot. I was a mommy of four children, including a set of triplets, and for years, spent much of my time with them and only kind of working on the side. Then I got divorced and my kids were grown, and I was working more and I looked at the headshot one day and was like this really isn’t 100 percent reflective of me today--And, there is more than one side to me, as there are to most people. I felt it was not just important, but imperative, to get new shots done.

I had met you at WeWork, and instantly, I could see that what you were producing was much more in the vein of what I needed. I remember looking at your work thinking “Oh, I can see these people are real. I see their wrinkles, I see their everything. I see real expressions on their faces...” They were very alive and not the sort of photoshopped, two-dimensional kind of photography you often see out there. Even though, of course I'd love to hide all my wrinkles, it was more important for me to look like me and to be projecting what you helped me to define for myself, what I really wanted the photos to say about me.

KK. Had we not met, what would have happened? What would you have done next?

CMD: I probably would have kept my one picture and felt sort of meh about it, you know. And when people ask me for a headshot, I'd be like, “Well, I have this, eh.” Which is very different from how I feel when people ask me now. A good friend of mine, who I worked with at Apple, now has her own PR agency. She's got great clients; Facebook, Adobe... and I ghost wrote a Forbes article for her and she said, “I want to put you on my new website. I need your photo and a bio.” And I immediately could say “Sure! I have like 10 photos to pick from. Which one will I pick? Which one is most appropriate for this?” Which was a very different situation than I had before which was like, “Well, I have this one and it's not really appropriate for this particular thing...” Now, I have a feeling of choice and a feeling of being proud of my pictures.

KK. Which picture did you end up sending her?

CMD: One from the series of pictures we took where I’m wearing a leather jacket and a very sort of feminine top with a high collar. That seems to really work for a lot of things because it says I'm serious, I'm a little bit of a badass, but you know I'm still a female. I'm still a woman. I'm a woman you probably don't want to F*$& with but i'm a woman. {Laughter} And that is a look that I seem to respond to and I often choose one of those pictures-- not every time though.

Another one I really like surprised me, because it's one I told you, I wouldn’t want any of these kind of pictures. I don't really like my teeth, my teeth are crooked and I don't really want to show them. I mostly smile, not a huge smile, not with my teeth and then you show me this picture- it's just me with a big smile, all the teeth, all the everything. Every wrinkle, every line. I love it! It's beautiful and it's joyful and very lively and very me and so that picture, surprisingly, I also use about as much as those.

KK: What was it like walking into the room and seeing pictures of you laid out on the table and set up around the room?

CMD: Oh yeah! I remember walking into this conference room that you had set up with these pictures, there were matted pictures leaning against a rail, ones laid out artfully on a conference table...And it was like wow! There are so...many... incredible pictures in front of me right now, of me. And not to say I loved every, single picture because, you know I'm critical of myself more than anything, it had nothing to do with your photography. But, I was blown away! I really was. I remember just thinking, how am I gonna pick? And I remember thinking in previous experiences of having my picture taken, “Am I gonna even find one that I like. And this time I had just the complete opposite reaction. It was like wow, there are so many great pictures. And so many great pictures that were so different from one another. I remember thinking, “I can't believe I'm not cringing looking at a bunch of pictures of myself.” You know, because as women, we're so critical. We're so self-critical. It was a really positive experience.

KK: Did anything shift in that moment or in hindsight, did you feel any kind of way?

CMD: Well yeah, after that, I then had all the ones I picked and I was like look. Look at what was produced of you. Anybody would say that's a beautiful picture or that's a fun picture, or that's YOU. Don't be so hard on yourself. It shifted-- I remember even with my kids, when they were little, I used to not want to be in the picture. I was very timid about having pictures of myself, and now on social media and stuff I tend to share more pictures of myself than I ever used to because I'm just not hung up about it anymore. Not all of the photos I post of myself look good, but we don't all look good all the time, you know. But I don't think anybody likes me less because I don't look as cute in a picture you know. I hope not. And if that is the case I shouldn't be friends with them.

KK: Exactly.

CMD: It was was kind of a bit of a breakthrough moment of self-acceptance. Right before our shoot, I had decided I was gonna move to New York. Here I am, trying to get back into the work world and sometimes you're in very competitive spaces and big players can be your client. Ironically, WeWork hired me to write some blogs and they said we need your picture and I thought Okay! I’ve got something that is worthy of WeWork; which is a very slick, very high-end everything with a whole look and feel and I thought, no what I have totally works, I didn't even have to flip out about it. Now, conversely, one of my colleagues was working on this as well and she said when they asked for a photo she freaked out, and then had to have her husband take a picture and then she was taking a selfie... and she said, “Well, I sent in the picture, but ugh, I don't know.” I thought to myself, you know, it's one of the reasons why I wanted to do this. I didn't want to be caught off guard. You just never know when you're going to need a picture for whatever reason. Sometimes I get a request and know it is really important that this be at a level and if you don't have something at that level, you can't come up with it overnight. And that's the way these things happen-- you suddenly need it that day or the next day and you’re S.O.L. And I didn't want to be caught unprepared giving them the “uh-I-guess-this-one's-okay” or “let me take a quick selfie” -- it's not acceptable in today's world if you're trying to be a professional. I look at my pictures and I think that's the level that I would expect of a female CEO.

KK: What were your expectations of the experience, if you had any, or of the shoot, before we actually did the photographs?

CMD: I didn't have a lot of preconceived notions. I wasn't sure what we were going to come up with, but I was just open to your process. At first we weren't sure where we were going to do it, and then we ended up doing it at my house and I wasn't really worried about it. At the time I was thinking, well you only have to get one good shot, because then I have a headshot right? So my expectation was well, let's just hope we get one good shot today. And then we got 500. [Laughter] So, it was a good day.

KK: How important was it that we shot at your house versus had we just done it in a studio?

CMD: I remember we sat on my landing at one point, which is one of my favorite spots in my house and we were out in my front yard and it just was a level of comfort and familiarity that I think is reflected in the photos. Being able to be at home with my things, with my guitar, in different environments that I liked— absolutely.

KK: We did not have a stylist but I did help you with some suggestions and stuff. How important was that aspect of it and how much did it help you or not?

CMD: You know, you may say weren’t a “stylist” but your input and guidance was absolutely essential. I wouldn't have known that certain things aren't going to look as well or certain things that I was like well maybe…? and you'd say yes! that will work, you helped to get me off the track of things that weren't going to work and you reinforced what was was going to work and you found other things, I wouldn't have even thought of. Remember we ended up using that green--- I don't know, it was like a poncho or something, you can't really tell what it is in the picture but it just looks-- it's a good color, it's a good texture, it looks great! I would have never thought of it. That was an essential part of the process.

KK: How would you describe what to expect to a colleague, friend, business associate etc..

CMD: It's not just a photo shoot. It is a very, intentional photo shoot with an excellent process for identifying and getting comfortable with what you're trying to project, defining what your intentions are for it. Having set that up from the beginning, you then go through the process of taking the photos and afterwards you realize, you accomplished what you set out to do. They were very specific intentions, so I accomplished these very specific things. So it's far more than a photo session. It is a defining and then a realizing of that. And then you go on to take the gifts of that forward with you, because you took the time to define those things. To figure out your priorities and what you want to project to the world—that sort of gets into your fibers a little bit and and then you have these photographs which then represent that and all of that is helpful in driving you forward with this sort of new found knowledge and understanding about yourself.

If you're thinking it's just a photo session you got it wrong.

KK: what have been some of the reactions you've received to your images?

CMD: Well, amazingly like the one picture where you know I'm big smiling and again lots and lots of lines revealed on my face and this and that—everyone loves that picture. I put a couple of them up on social media after we did them and that one got probably the most likes, by far, of any of them.

KK: What were the three biggest benefits of working with together and using the Photos?

CMD: One, going through an intentional process and therefore getting great pictures I really wanted and could use. Two, not just getting “a headshot”, getting a huge variety, I can use for different purposes, because I do have various needs. Three. that you were so easy to work with and responsive and presented everything so beautifully in the end. You're the third benefit. The benefit of working with you just made it painless and I think ultimately I ended up making good choices because of that. I wasn't frustrated or feeling like I was spending too much time on it. It was just a really nice process that allowed me to get all the way to the end and make good decisions

I would say the other thing that I learned is. Go ahead and tell Kat what you hate and you don't want to photograph it. She'll photograph you like that and then you'll love it! {Laughter}

KK: (Laughter) I was watching an interview with someone who had done a trek with Bear Grylls. And in their pre-interview were asked, what are the things that you're really afraid of —and asked in a way that gave the impression the result would be to avoid those things, right? But instead it was like oh you're afraid of heights? Awesome! We're gonna pick you up on a ladder coming off of a helicopter and we're gonna go straight up. That's gonna be the very first thing we do. You’re scared of bugs? Awesome. We're gonna eat bugs.

I don’t take it quite that far, but I do believe we discover a lot and grow when we are outside of our comfort zone. Getting your photo taken is already outside of most people’s comfort zone. It’s very personal and vulnerable and I don’t take it for granted that everyone will be so open.

CMD: I’d say, be open. Because you never know. The one you think you're going to hate the most might be the one you love the most.


Hello Gorgeous exists to help the world smile. We design and lead improv workshops and portrait photography for teams and individuals to upshift their self-image, self-confidence and authentic connection with themselves and others. Schedule your free consultation to find out more here.


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