How I learned to love my photo.

As I slid my 5th grade class photos over the kitchen table to my mom, I imagined several possible reactions:

1. “Wait, why didn’t you tell me you had picture day??”
2. “These are nice… >Pause/Sigh< …when did you take these?”
3. “Oh my God. When is retake day?”

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I couldn’t blame her.

Photography — more specifically, fashion photography — is part of my family crest, at least on my mom’s side. My mother’s distant cousin was the first Estée Lauder model. My grandmother modeled for Bonwit Teller, and my aunt was a fashion model and fashion coordinator. Good photos, in volume, are part of the family legacy.

Which is why it’s not helpful I’ve had a love/hate relationship with headshots pretty much my entire life. I don’t think I’m alone. I’ve yet to meet someone who says, “I love taking headshots!” (except maybe the photographer). My negative photo feelings find their origin in middle school.

When I was 9 years old, we moved. For my first days of 4th grade my mom, a Chicago fashion model, actively tried to help me fit in the best way she knew how. She weighed in, hard, on my school outfits. ?For my 4th grade photo, I look like a cherub. Honestly, it’s my favorite photo ever. I look happy. I’m wearing my favorite white turtleneck and checkered poncho.

My cheeks are rosy, and it was honest-to-God, the last good haircut I enjoyed in middle school. In later years, my mother was convinced I’d look good in a Dorothy Hamill haircut (I didn’t) and even more convinced a perm was just the thing to offset my increasingly chubby face (it was not).

I gained 15 pounds between 4th and 5th grade. What I didn’t realize in 4th grade, but I did by the summer, was the move signaled the beginning of the end of my parents’ marriage. I guess I unconsciously managed my stress around it through frequent trips to Poppin’ Fresh Pies restaurant. Chocolate Silk pie is not kind to your waistline. Thanks to the weight gain, my 5th grade gym teacher decided a good nickname for me would be “Miss Piggy” (not sure why Jennifer didn’t work for him). Yeah, 5th grade was that kind of year.

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Given the amount of time my mom was out on modeling jobs, she missed the typical school stuff: Parent/Teacher conferences, Student Art Day, the Spelling Bee (I went out on the word w-a-t-e-r-m-e-l-o-n…it vexes me to this day) and Picture Day.

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I was on my own for 5th grade picture day and, well…how do I say this? I forgot. I completely forgot. I realized I might’ve forgotten something when I saw several girls on the playground all gussied up. Then it hit me when a couple of boys, who’s eyes I’d never seen, I saw for the first time thanks to perfectly parted hair. Ugh. It was picture day. Suffice it to say, I was not ready.

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My greasy and uncoiffed hair were easy proof I’d hit snooze a few too many times that morning. Although I was wearing my favorite long sleeve t-shirt, emblazoned with The Fonz saying “Aaayyy!!”, this was not a look worthy of a fashion model’s daughter. These were the photos I slid across the table to my mom. Those photos no longer exist.

Now you might think all my hang-ups come from having a fashion model mom, but she isn’t to blame. I will blame her for the god-awful matching outfits she dressed me and my sister in, but not my photo hang-ups. The funny thing is – I loved that photo of me in the Fonz t-shirt. Even though my mom certainly would not have picked it as her favorite of me, she never shamed me for it. If I recall, she blamed herself for not being around to help me pick an outfit.

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I was more vigilant for 6th grade. What better way to make up for the disastrous 5th grade photo then by having a perfect 6th grade photo? Except it wasn’t.

Perfect, that is. This time, I overdid it. I wore my favorite overalls and t-shirt and white wool sweater and hair comb. I wore my favorite everything. You know the expression: too much of a good thing? That was me in my 6th grade photo.

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Thus began my love hate relationship with headshots.

Whether I prepared for them or didn’t, they never seemed to turn out right.

And by right, I mean having a picture that I wasn’t afraid for family or friends to see. A photo that reflected I was the daughter of a fashion model. More specifically: that I understood photography.

Last month, I finally overcame my aversion to headshots.

I realized, how you feel about a headshot comes not only from how you feel about yourself but from the experience you have with the photographer. I knew this subconsciously from watching my mom at her photo shoots, but I don’t think I ever internalized it. Until now.

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To take a great photo that captures who you are – YOU have to feel comfortable with who you are. And the person on the other side of that lens plays a critical role in helping you see the best version of you. I witnessed this photographer/model dynamic with my mom and whoever was taking her photos.

My headshot experience, however, has been more the “Get your FREE LinkedIn headshot at our event!” type. Moments marked by bad lighting, bland backgrounds, and rushed photographers = no connection.

Exhibit A

Taking these types of photos can make you feel like you just can’t take a decent headshot.?

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I never quite got how taking your headshot should feel until my photo session with Raj Bandyopadhyay

It was transformative.

His preparation has you think about:

·????? the mood you want to capture

·????? how people should feel looking at your photo – looking at you

·????? why this image is important to you

?Intentionality is the operating word.

The preparation for the session and the actual experience forces you to be thoughtful and considerate of every step. As a result, you see yourself in a completely new light. It’s a wonderfully transformative experience. I learned you don’t have to be a model to deserve this type of experience.

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Thank you, Raj.

P.S. Watch here for the results of this wonderful experience. Coming Soon!