How to Take Great Headshots When You Hate Having Your Photo Taken

I hate having my photo taken.

I’m not one of those girls who says, “I’ll take the picture, I don’t want to be in it,” but I certainly think it. My image is never something I’ve been comfortable with.

I don’t like looking in the mirror, especially in the morning when I’ve just woken up. My skin is flaky, my eyes have gunk in them, and my frizzy hair is up and wild. It’s not a pretty sight. I also don’t like looking in the mirror at the end of the day when my makeup is wearing off, my hair is falling flat, and I look more worn out than when I started my day.


The last professional photos I had taken were in Central Park in April 2015. I needed headshots for my business, so I enlisted my friend Sophie, an incredibly talented photographer, to take them. She made me feel comfortable and safe in front of the camera, but that doesn’t mean I enjoyed the process. I liked two of the photos she took and used one of them regularly on social media and when I was featured in any press or articles.  I liked how my hair was blowing in the wind.

I never publish many of the other photos Sophie took. I looked uncomfortable. I felt uncomfortable. I had a stiff and forced smile. My rolls were showing. I looked so pale. I had a double chin. My hair was out of place. I spotted a stain on my shirt. I had bad posture. I didn’t know what to do with my hands.

I didn’t get new headshots for years. Last fall, I started working with a coach, who suggested I take new headshots during my annual winter trip to Tel Aviv.

“It seems you’re happiest when you’re there so why not be captured in that moment?”

She was certainly on to something.

Six weeks into my trip, I decided to reach out to my friend’s cousin who’s a designer to see if she was open to taking my photos. I suggested we do them in Neve Tzedek, a pretty neighborhood in Tel Aviv where there are bright colored walls, blooming spring flowers, and unique architecture.

I booked an appointment to get my hair and makeup done. I walked in with hair inspiration and stated the importance of still looking like me, having a natural yet upgraded look. I didn’t want to look like I had pounds of makeup on. I wanted to be approachable.  

The woman was running late. Forty-five minutes late. They told me nobody else could start the process. I reminded them I had an appointment; I wasn’t just showing up. They didn’t seem to care. I sat at the counter, staring in the mirror anxiously waiting for someone to fix me up. After over thirty minutes of waiting, the woman at the front desk started doing my makeup. She sort of seemed to know what she was doing. The woman finally arrived, not speaking a word of English, and did my hair. I was already uncomfortable — staring at myself in the mirror for too long and feeling anxious about soon being photographed. The lack of communication with the stylist didn’t help the situation. I was worried the curling iron was going to give me tight curls which is not me. Fortunately, she recognized what I was looking for and made it happen.

After the appointment, my photographer and I walked around looking for spots to take the photos. I’d stand against walls, trying to look natural while feeling extremely uncomfortable. I’d lean my leg against the wall and wonder if I was making things better or worse. It started getting warmer and warmer out so I was beginning to sweat. I’d pat my forehead and upper lip to get rid of the visible sweat. Obviously I was wearing black to hide any rolls or imperfections so that wasn’t helping with the temperature rising.

When people walked by, they stopped until she got the photo. We both realized that the moments after she took the photo — when I let out a minor giggle — was when we got the best shots. It wasn’t forced, it was me genuinely smiling and laughing at the situation. I wondered what these people were thinking. Did I look stupid? Did they question if I was “somebody?”

We spent a few hours walking around, stopping, posing, shooting and figuring out what worked best. We ended up at a gluten-free bread pop-up, and after taking a few final photos, I decided whatever she had gotten was enough. I was done. Being in the spotlight made me uncomfortable, and I was ready to call it a day.

I spent the rest of the day in my new black linen jumpsuit (that I’d later realize when I got the photos could have used some ironing) with a face of makeup and curls created by a curling iron. I looked better than I usually did and tried to walk with confidence with this upgraded look.

A few days later, my photographer sent me 12 photos (out of the hundreds we took) to review. They were the ones she thought were the best. I was anxious to see how I looked and how I would feel about them.

I was surprised. Out of 12 photos, there were five that I genuinely liked. I actually liked how I looked. She captured me in the right sun, with gorgeous backgrounds and smiles that were authentic, not forced. I liked them enough to want to integrate several of them into my website. I even shared three of them with someone who interviewed me for a podcast, saying, “This is super out of character, but I truly don’t know which one I like the best. Whichever you want to use, go for it.”

Photos by Dana Fisher

I can’t say taking headshots is a process I want to go through again anytime soon, but I’m glad I did it. Especially while I was in Tel Aviv, my happy place. I may not have felt comfortable throughout the process, but there were moments when I laughed and smiled and the discomfort faded away, and it was a surprise to see that captured on film. For me, it was a nice change of pace.