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Becoming a Professional Photographer in Midlife: Alyssa’s Story

Published on 03/04/2019

After a long career in fashion and design, a midlife layoff and first marriage found Alyssa grappling with what to do next. A camera from her new husband would be the catalyst for Alyssa to tap into her lifelong passion for photography.


Tell us a little about your background.
I was born in 1968 in Bronx, New York, and moved to Rockford, Illinois when I was six years old. I am the middle child of three girls. While my older sister is a sports fanatic and my younger sister was the smart one, I was the artistic child. Being a Pisces, that is the deal!

Our family, circa 1978

My mother was a high school math teacher then stayed home once my older sister was born (I am the middle of three girls). Still, she always took on leadership roles in non-profits like American Cancer Society (ACS), our Temple sisterhood, and Haddasah. She started her first business when I was in third grade. It was called Initially You and the format was home shows like Tupperware. Products included cotton tops, skirts, and bottoms embroidered with one’s name or initials. The business started in the guest bedroom of our house and soon took over the entire basement. Eventually, Mom had 40 reps around the country and moved the product into a warehouse. Her second business was Samco, named after her father Sam. Samco was a promotional products business. I guess there was a lot of monograming and personalization/logo imprinting there too. I never made that connection before.

My mother was an entrepreneur before I understood what the word meant. To me, she was a mom who had interests and created a business doing what she enjoyed doing. At the time, it was so embarrassing that she would talk to anyone and “interview” them, then tell them about her business. If she saw a garment that she liked, she would ask to look at the label inside the shirt some stranger was wearing. If you were fortunate (or unfortunate) enough to sit next to her on an airplane, she would know your life story by the time the plane landed. The truth was she loved her businesses and worked at them 24/7. I didn’t appreciate it at the time, but I do now. I understand now that she was always networking, making connections.

My mother featured in an article for a patent she has for comfortable high heels. She is always thinking business!

What I got from my mother was confidence in myself. Confidence that I can speak in front of others, speak up for myself, and lead. From a young age, I saw her on the bema at Temple, speaking in her leadership roles or lighting the candles at services on a Friday night. When my mother walks into a restaurant, she knows at least one person. When I was in high school, I was encouraged to run for student body and my reply to my friend was, “My mother will love this.” As high school Class President for two years and a keynote speaker at the graduation ceremony, I have spoken in front of hundreds of people and I love it. The poise and leadership skills I got from my mother.

My father was in the men’s shoe business. He died in 2010, at the age of 72, two days after my parents celebrated their 49th wedding anniversary. After his death, my mother sold her business and retired. My father started out as a young kid selling shoes in a shoe store and worked his way up to an Executive at US Shoe Corp. When we moved in Rockford, Illinois, his office was in Beloit, Wisconsin, 20 minutes from our home. Sometimes, on weekends, he would take me and my sisters there and we would get to see how the shoes were made right there on the factory floor. US Shoe also worked with factories around the world and my father traveled to them all. At one point in time, we figured that he was away from home almost 1/4 of the year. He would travel to the factories in Italy, Greece, Spain, and eventually India. We would have foreigners from all over the world visit us in Rockford and come to our home for dinner.

My dad at a shoe factory in India

Years later, when I worked in the fashion industry, doing the same role as my father but for women’s apparel, I would visit factories across the world and then have visitors from foreign countries come for dinner at my childhood home to sit at the same table in Rockford. I truly feel that I have walked in my father’s shoes. I wish he had been alive to see it.

My father was an artist at heart. As a child, he painted and as an adult, he taught me about art. We would spend the weekends in the basement watching studying art along with my easel, acrylic paints, and charcoals. My father was a true renaissance man who loved classical music, art, photography, philosophy, and sports. He tinkered in photography, taking pictures of nature and architecture.

I am a combination of both of my parents. My mother as the entrepreneur and leader, my father as the fashion industry executive who traveled the world, and artist.

I attended the University of Illinois, Champaign-Urbana class of 1990. I graduated with a BS in Marketing of Textiles and Apparel with a minor in Business Administration. When I started to look for jobs, my eyes were only on New York City. I had always loved the energy of New York and kept an “I love NY” bumper sticker in my childhood bedroom window. I was putting it out to the universe that was where I belonged. My first job out of college was as an Assistant Buyer at Ann Taylor, Inc, in New York City. I had graduated in May and was living on West 57th Street by June. I remember the first week I was employed at Ann Taylor, I attended the Annual Managers Meeting at the famed Plaza Hotel. My dream had come true, and I sat there in tears of joy. The following year, I was asked to model in the fashion show part of the meeting and that was a real thrill!

Me with my team at the factory in Sri Lanka when I worked in the fashion industry.

I stayed at Ann Taylor for four years; by then I had realized that it wasn’t creative enough for me. I needed something where I played a role in the creation of the product, so I went to work for one of my vendors Isabel Ardee. For seven years, I was the Head of Merchandising, where I was in charge of everything involved with the creation of the line, including design, fabric, color, sample room, sample sewers, pattern makers, fit models, and private label sales to retailers such as Neiman Marcus, Bloomingdale’s, and Ann Taylor. One of the perks of this job was traveling to Paris twice a year for the fabric exhibitions.

After Isabel Ardee, I went to work for the Italian motor scooter company Vespa. Wow it was cool! I was the Design Director responsible for creating a clothing and accessory line for the iconic brand. I researched the brand inside and out. I even went to the Piaggoio factory in Pontedera, Italy, where the scooter is produced and visited the exclusive Vespa Museum at the factory. From this and further research, I created the Style Guide that I presented to the President of Piaggio in Italy. When we relaunched the Vespa in the United States in 2000 after a 20-year hiatus, the launch party was at Paramount Studios in California with the throwback theme of Roman Holiday.

At an event for Vespa with Peter Laitman former VP of Vespa, USA.

Following my experience at Vespa, I fell back into garment production, where I spent 10 years as a Senior Account Executive at Ventura, a private label company based in NYC with factories in Sri Lanka. I loved this job because it allowed me to have a team here in NY and a team based in Sri Lanka. I would travel there a few times a year and, like my father, would visit the factories and check the production lines, meet the people, and learn about the culture. Although my ultimate responsibility was to sell our production capacity to the major retailers in the USA, my favorite part of the job was to teach my staff, both domestic and overseas, how to manage and run the business. It was most rewarding to work with the overseas team to have a sense of ownership for their work and to be more assertive. I trained my team so well that they were able to manage the business directly with the clients. At this time, the company was downsizing and moving most of the tasks to the team in Sri Lanka and, since I had prepared them to handle the work, I was relieved of my duties and was ready for my second act.

I got married in 2012, at the age of 44. Up until this time, I was an avid traveler. I took advantage of my singlehood to travel to places like Africa (twice), Croatia, Argentina, Thailand, China, and Turkey. I owned my own apartment and was living the NYC lifestyle.


When did you start to think about making a change?
I was laid off only four months after my wedding. I was transitioning from being single for so many years to being married and now had to find a job. Every morning, when my husband left for work, he’d look at me still in bed and say, “Will you look for a job today? Did you call the headhunter? Did you send your resume out?” Each question was like a dagger into my heart. I knew in my soul that I no longer wanted to work in the garment center, that it was no longer my passion and that I didn’t want to sit at a desk anymore. For about six months, I played mindless games on my cellphone and avoid looking for employment. Yeah, I would send a resume here and there, but I really didn’t want to get a job. This is what I call the “emptying the tank” era of my life. I really emptied my brain in a way it was a sort of meditation. Empty.

Then it struck me. I wanted to become a professional photographer. When I first started dating my husband, Barry, in 2010, his first present to me was a digital SRL camera; he’d noticed that no matter where we went, I was always snapping photos. I started early in life, taking photos as a kid with my Polaroid or Disc camera, later the Elf, even a disposable camera, whatever I could get my hands on. Barry knew photography was a passion of mine and that this would be the perfect gift. It even compelled me to sign up for photography classes after work.

Behind the scenes of a photo shoot on location at the client’s home.


What is your next act?
I am a professional photographer and artist based in New York City. My business, Peek Photography, focuses on women in business over 40, for their headshots and personal branding. My art business, Peek Photo Art, sells my artistic photography to interior designers, home furnishing stores, and art shows, I addition to direct sales. I have been seen in the UK publication Home and Garden magazine and have sold over 200 works of art to date.

When I work with women, it isn’t so much the photography that I love but instead the transformation of my client. A transformation that is much more than a pretty picture with hair and makeup but about that moment that they accept that they are beautiful just the way there are. I coach through my camera. “Is that really me?” They say when they see their photos. I’ve also been told I have “a way of bringing out your best self” and of “letting your little inner girl come out and play” I focus on women over 40, business owners and professionals, because they need to be seen but are not running toward the camera. They are doing everything to avoid seeing their age and their so-called imperfections. By catering to this niche, I have a created a safe place without judgments.

On the left is Susan’s old Facebook Linked In photo and on the right a photo that represents who she is a vibrant
beautiful woman. Her transformation was incredible.

I also can personally relate to my clients’ concerns. When I was younger, I was extremely skinny and very tall. My biggest issue was that I couldn’t keep weight on. I remember in college that I would keep a big box of Snickers under my bed and drink Ensure protein drinks to get calories into my body. Most people think that being tall and thin is the answer to being happy, but I will tell you it is not. I got called names like noodle, string bean, and thin air. Someone once said to me that if I turned sideways, they wouldn’t be able to see me. I never let it depress me, but I didn’t make the realization that the magazines and society make people believe that if you are thin you will be happy, and I don’t agree. I believe what makes someone happy is not related to size but rather self-confidence and self-love. Looking ageless has nothing to do with how smooth your skin is but rather the energy you put out into the world.

I coach around this belief. By encouraging them to envision themselves at their best today and in five years, I help them see that they are they are beautiful and start to believe it. Don’t get me wrong, these are accomplished women, confident women, but they don’t know what to do in front of the camera. The don’t know how to “be” so It is a sort of role playing, of stepping into the mindset of their success. Clients have told me that they put photos I took of them on their vision boards. Think about that: They want to become the person that they already are; they just need to own it.

Before and After: A great example of this Interior Designer’s previous business profile photo and new image.

Funny story: I called a psychic years ago in the hopes she would tell me that I would eventually get married. I had long forgotten about this when recently, my notes from this session that read “People are leaving your company and you will be one of them. You will be a coach and help people with transformation.”

As I mentioned, I also sell my artistic photography. Anyone can take a photograph, but it’s what I do with the photo that makes it unique. Either in camera or post production, I transform an image or a scene into something one not only sees, but also feels. Sometimes it is like a meditation for me. I don’t know exactly what I am doing but when I look at the image, I have created something I didn’t know I was doing.

Title of the work is “Ditch Plains.” It’s hanging in the home of a client.


How hard was it to take the plunge?
Once I decided photography was my second act, I went for it. I Googled everything about photography and attended Photo Expos and was on the edge of my seat the entire time, soaking up every bit of information I possibly could. I couldn’t get enough.

When someone asked me what I did I replied, “I am a photographer.” I remember the first time I said that, my husband looked at me like I was nuts. But if I didn’t think of myself as a photographer, then who would? I needed to declare what I wanted. I said it out loud, to everyone I encountered. Then one day, I was invited to a women’s networking meeting. I remember getting dressed that morning and putting on a black blazer and it felt so wrong! I felt so confined and that I was playing the wrong role. I was a creative. I was a photographer. I was not going to wear a structured blazer. I changed my outfit to a stylist knit top, leather pants, and high boots and scored my first client!

That client brought me other clients. That first networking meeting brought other networking meetings and the ball was rolling. I was like a chicken with my head cut off running to every women’s networking event in the city that I could find. I made business cards, created a website, started a Facebook page and Instagram account. I was Alyssa Peek of Peek Photography. My years of public speaking and being in leadership roles had prepared me to get out in front of people and talk about my business. People talk about the “Imposter Syndrome” they experience, but for me I felt more like an imposter at my fashion industry jobs.

The “after” photo! Beautifully posed with a display of confidence, charisma and beauty.

Being a photographer, an artist. This is me! My biggest regret is that my father never saw me live fully expressed, using the tools he had passed on to me and make a living out of it.

My sister often tells me, “I have never seen you happier. This is who you are and what you love to do. I am so proud of you.”

At the same time, I was also developing my photography art business. When I got the camera and discovered photoshop, I started to create artistic images of landscape photography. When a friend asked me to participate in an art show she was organizing at her store, I was beyond thrilled and sold my first three pieces of art. Both the personal branding photography and art photography are about transformation, whether it’s a photo of a woman who now sees herself in a new light or a tree blowing in the wind that makes someone feel an emotional attachment to it.

Showing my art in an art show a the Wild Horse of Sable Island Gallery in NYC last Spring. This piece is called “The Upside Down”.


How supportive were family and friends?
Everyone has been so supportive. Friends from all parts of my life have stood in front of my camera and purchased my art. I have photographed friends from my childhood for their business profiles and it was a friend who first asked me to show my art in her store. Other friends have connected me with their companies, and I have done large projects for them. On line and off, my friends and family are my biggest fans. When my 15-year-old nephew said that for his birthday he wanted a piece of my art, that was golden!

End product, a photo that my client is proud to share with the world. This image was even on NYC taxicabs to promote her real estate business.


What challenges are you encountering?
My biggest challenge is sustainability. Every sale is a one-off sale. My clients come for a new profile photo but that lasts anywhere from 2 to 5 years. So it’s a numbers game to keep the cash flowing. This is how the art helps fill in the gaps. Even with the art it is a struggle sometimes to create new work and then to get it in the hands of others.


What did you learn about yourself during this process?
This journey has helped me confirm what my parents taught me, “that I can do anything if I put my mind to it.” I have learned that I am determined, likeable, and creative. I have learned that how to run a business and how to promote myself. I have learned to value my work, my time, and my relationships. I have learned that if you don’t try, you won’t succeed. I have learned to ask for what I want. I have learned that I am determined not to fail. I have learned that I do not want to work for anyone else or be in an office environment. Being a business owner, I make my own schedule, work when I want to, and take the jobs that I want to. I have learned that what I always wrote as my goal in life has come true: “I want freedom.”

Speaking in front of a group of women talking to them about the importance of a power presence
both on line and in real life. Also giving some great posing tips on how to look their best on camera.


Looking back is there anything you would have done differently?
I would have had the discussion about starting my own business with my husband before I just decided to do it. But besides that, no. Every mistake and mis-step has only taught me to be better. The one thing I don’t do well is my own marketing and systems/funnels. It’s not too late but I wish I had invested early on to create a solid foundation and business plan. I am not a good planner so having a solid business plan may have made a difference, but I am happy where I am today and so proud of all my accomplishments.


What advice would do you have for women seeking reinvention in midlife?

  • Go for it.
  • Believe in yourself
  • Tell everyone you know and everyone you don’t know about your business
  • Have a target audience clearly defined
  • Try, fail, try again.
  • It’s never too late


What resources do you recommend for would-be professional photographers?
For me what really helped me get started in photography is creativelive.com, a learning site with live and recorded classes on so many areas of being a photographer from how to use your camera to posing, post production, and marketing. They now have a much broader reach to other industries.

Photo Plus Expo is a 2-day exhibition with classes and products for the photography/video industry.

On YouTube, you can learn anything about everything, including photography.

Sea Change Networking is a great class on how to network, with important lessons. I’m also a fan of the networking group Empowering a Billion Women by 2020. To me, there is nothing like in-person networking. I find that I like the smaller groups much better than a large conference. Knowing your target audience is key so you can network with that audience AND the people who know your audience.

BNI is a Boot Camp of Entrepreneurship. It’s not for everyone and honestly, it’s too structured for my style but I was a member for two years and it brought me business. More importantly, it taught me how to say my elevator pitch, how to refer people, and how to be committed.

“Blue Sailboats” – One of my very first pieces sold and my best seller!


What’s next for you?

I will continue to grow my current businesses and add in paid public speaking. I have presented to groups and organizations offering a safe space for women to express their fears of being photographed and discussing how their online image can be a tool to their success and how to look and feel their best on and off camera. I am looking to speak in front of larger audiences in the area of corporate diversity programs.


Connect with Alyssa Jae Peek
Email: alyssa@peekphotography.nyc


Art photography:

“Alyssa had an entire room of 25 professional women laughing, sharing our innermost fears of self-photos, and embracing how our headshots can be used to boost our personal brands. She is engaging and insightful, with practical tips that make even the most camera shy let down their guard.” ~Marla Persky, WOMN LLC

HeleneTStelian Musing
I’m Hélène Stelian, the Midlife Mentor with a passion for facilitating personal development in women 40+. Through my THRIVE Courses, I help introspective, curious, action-oriented women 40+ deepen their journeys of self-discovery and growth—and create their next chapter with courage and intention.



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1 Comment

  1. photography

    First of all, I am so happy to see your complete family photos. In the above content, you have written that your mother was a high school teacher. I think your mother plays a vital role in your life because with mother support you cannot make a professional photographer.


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