My LinkedIn profile photo was taken 12 years ago at my surprise engagement party. My now husband orchestrated the whole party so he could surprise me again the same night he shocked me by getting down on one knee in a snowy courtyard in Chicago. After I accepted his proposal, he told me that he had arranged for some friends to go out with us to celebrate the happy news. In fact, when I arrived at our double dates’ apartment, it was full of all our nearest and dearest and flutes of champagne.

The hostess of the party just happened to be a professional photographer, and she had her pro camera clicking away throughout the night. These candid shots of delight, surprise, and joy are some of my favorite photos of all time. 

I waited a respectable five minutes after this talented friend posted the party photos on Facebook to crop my brand new fiance out of my favorite snapshot of us and paste my beaming high-res face into the little LinkedIn circle. That little circle has represented me to the professional world ever since. 

I’m on the job hunt now for the first time in over seven years and my photo needed a refresh. Look at “engagement party” me and look at “now” me, and you can definitely tell that the old photo was about thirty pounds, a dozen years, a kid, a pandemic, and several thousand gray hairs ago. 

I texted my ride-or-die Roxanne, who is also a pro photographer (How fortunate am I that I know and love so many talented, creative people?), and booked a creative portrait session. She was delighted to work with me for this photo refresh, and we set a date for an outdoor “business casual” photo shoot during the week my daughter would be at camp all day.

That date got rained out.

Thank God. 

Of course I had waited until the night before to start trying on outfits from my former life as an office professional. And of course not one of those tops, blazers, or dress pants fit. Not one.



When Roxanne and I texted about rescheduling the shoot for the next morning, I offered up an actual prayer of thanks for the rain delay and talked Les into agreeing to sit in the car with a book after our belated anniversary lunch that day so I could shop for a new outfit immediately after indulging in my favorite tapas and red sangria. 

After leaving my beloved to his own devices in the parking garage, I walked into Ann Taylor and started loading blouses and blazers over my arm. The sales associate started a fitting room for me while I scoured the clearance section. 

Sue was an excellent sales woman. She was honest and helpful and sympathetic. “I don’t fit into any of my professional clothes anymore”, I told her with tears eeking out the corners of my eyes. “Oh honey, you and every other woman who walks into this store these days.” I’d like to tell you that I found one perfect professional-looking combo and it was on sale and that I felt totally relieved.  

Not so, my friends. I panic-bought $400 worth of new workwear (Sue assured me that I could return what I didn’t use for the shoot), tried it all on in different combinations at least a dozen times at home, and tossed and turned all night that night while my anxiety screamed into my ears that I would look ridiculous, that only realtors and bank tellers wore blazers, that the new pink top was still too tight, and that my career had probably peaked four years ago. 

I feared that once I saw the photos of myself there would be no denying that I had aged and softened dramatically. I would have to face it. And not just face it myself, but thrust my profile photo and my resume and my roller coaster work history into the hands of potential employers. And let’s be honest, it can feel cringey to think about having photos taken of just you and your own face. Not family photos. Not a couple’s session. Nobody else’s torso to hide half of yours. Just you. 

So yeah, I didn’t sleep much the night before our rescheduled shoot. 

I arrived at our rendezvous point wearing my favorite goldenrod linen dress and my denim jacket and had hangers with my all time favorite burnt orange poplin top and jeans, and a pink chemise with a black blazer at the ready. Roxanne greeted me with her ubiquitous beaming smile and a huge hug. I was still trembling with the roil of anxiety, but it started to ease when I remembered I was in good hands. 

Roxanne and I have been friends since we both had a crush on our French TA in undergrad and we have been close to one another through SOME STUFF in the last twenty three years. In addition to being the #1 person to call for driveway margaritas in a pandemic, she has also been our family photographer since she started her photography business a few years ago. She has captured everything from my daughter’s baptism to our Christmas card photos to our emergency family + elderly dog photos taken in the last days of our beloved chihuahua’s life. It seems entirely fitting that she would be the one to coach me through the chin tilt and hand placement awkwardness of a portrait session as I queasily launch myself into a new career wilderness. 

I wasn’t at all worried about the quality of the photos because I knew for a fact that she would get some great shots. The anxiety was feasting on my self consciousness and existential angst.

Roxanne had scouted some remarkably flattering brick wall backdrops – yes, flattering walls are a thing – and cheered me on through hundreds of clicks and outtakes and wind-swept hair. She had a Girl Power playlist for inspiration. She kept me laughing and moving and smiling real smiles. It was – dare I say it – SUPER FUN. I even got to experience the rare thrill of changing into a different shirt outside with no cover – “Cheers!” to anyone who happened to drive by the parking garage side of the alley where I was posing. The biggest, weirdest rush I have had in public in a while. 

Note: You do not need to risk a Public Indecency citation to have a successful portrait session. We were rushing to beat the rain that had started to sprinkle again and didn’t want to risk a new downpour in the time it would take me to duck into a restroom to swap outfits. 

Roxanne sent me the edited batch of the best shots from our shoot, and I am so happy with them. Of course, you’re not going to love 100% of the photos taken of you, but there were a lot that looked professional AND really looked like Right Now Me. Me with the gray hair and bigger clothes and cheek dimples and bright lipstick. The person who is about to run after new job opportunities and is still processing her quickening creep through middle age. She’s strong, she’s wobbly, she’s rounder and crinklier than the person glowing in the engagement photos. 

She’s a hell of a lot more experienced. And she has plenty to offer the world. 

When I look at Right Now Me, today, through those photos, I’m thankful. Imperfectly, self-consciously thankful. Have you looked at yourself recently and really taken the time to see yourself? To thank your body for getting you through this past year? To notice things like how well your legs have aged, actually, and how you can wear a whole new color palette now that your gray hair gives you an almost platinum-blonde look? 

To think back over all the creme brulees you’ve let yourself savor, and all the moments you’ve said YES to a delight you would have denied yourself in your orthorexic youth? (I’m looking at you, gluten free lemon blueberry muffins from Blackberry Market).  

You do not need to wait until you feel like a model or a rock star (or, ahem, a published author?) to get a photo session. I recommend it. You may even get to do some shopping and whip your shirt off in an alley. It’ll be fun. 

Check out Roxanne’s work at www.hawaimages.com

2 thoughts on “Headshots

  1. Jill the “Right now You” is absolutely gorgeous. I mean the very dazzling, real, smile. Your figure and outfits stunning! Your photographer generous and talented. God bless the job search. Whoever hires you will be so glad they did!

    Liked by 1 person

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