Picture Day Header

My picture day, that is.

When I decided to try my hand at entrepreneurship, I knew that I wanted to do it right. I finally found a domain name I liked, along with all the social media handles to go with it. I scoured the internet for just the right website design and mapped out all the pages I wanted to make sure to include.

Part of building a new website (in hopes of building a new business) meant getting some pictures taken. As someone who’s much more used to taking care of business behind the scenes, I must admit I was a little nervous.

First things first: finding a photographer.

YPPHaving lived in New York for as long as I have and having worked in theater for several years, I’ve been lucky to see the work of a lot of very talented photographers. But I didn’t want to spend the day feeling uncomfortable in front of a camera with a total stranger!

Once I decided to look closer, my decision was easy. I had seen Jeni Magana capture another friend of mine so she not only looked beautiful, but more like herself than I’d seen in other pictures. And that’s all I wanted: to look nice, but like myself.

So, having settled on a photographer, I moved on to the more stressful questions.

(1) What should I wear?

LoftFlutterTopI assisted a casting director for a while, which means I’ve seen more than my fair share of headshots. And even though this shoot was somewhere between headshot and lifestyle shoot, I knew that I should (a) depart from my usual black/grey palette and (b) KEEP IT SIMPLE.

I knew I wanted to wear jeans and my oxfords, but I needed to find a shirt. I finally settled on this flutter sleeve number from LOFT. The color seemed good, and (bonus) I got it for less than $20 thanks to a sale and coupon code.

Jeni wondered if I had done some research since that was the color she had pictured me in, which I took to mean one thing: SUCCESS!

(2) How should I do my hair/makeup?

drybar UWS

You would think that by this point in my life, I would know how to do my own hair, but I decided to trust this one to the professionals. I booked a session at drybar, and called it a day. It was a little curlier than I usually like, but I figured they would loosen as the day went on.

My friends at European Wax Center took care of my eyebrows that morning, but I was on my own for makeup. I could have gone to Sephora or a department store for help, but I wanted to look like me, and me just doesn’t wear all that much makeup.

I’m sure I have Photoshop to thank as well, but I think all in all the end result is what I wanted. Me+, if you will.

(3) Should I use props?

I knew that Jeni and I would be spending the day exploring New York’s Upper West Side. That meant I probably wouldn’t want to carry too much around with me. On the other hand, we agreed that we wanted at least some of the pictures to reflect my “getting things done,” which to me meant my laptop (hello, adorable rose gold MacBook) and at least one notebook (it took all my strength to just pack one).

Both items did make it into some of my favorite shots, but it was a pain to lug everything around all day. As a mom, I’m pretty used to carrying a giant bag at all times, but it’s definitely something to consider if you’re not that kind of person.

Even though I still cringe a little thinking about how awkward parts of that day were, I’m really happy with a lot of the pictures I got out of it. I’m no model, but the new pictures are scattered around the new site and I love it/them.

Now, how long before they’re considered outdated…

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