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Becoming a Professional Artist at 53: Jill’s Story

Published on 11/25/2020

It took a snowy day when Jill was stranded with only paper, a hole puncher, and glue for her to discover a hidden talent and launch her new venture: hole punch art.

Tell us a little about your background.
I grew up in Highland Park, Illinois, a 10-minute drive from where I currently reside. I am the third child of three girls, each of us one school year apart. My parents met at a fall dance in Chicago while home from college for the weekend and were married the following April. They are an atypical prototype for marriage as they always made it look easy. My sister Lisa and I are what some call Irish twins, and my sisters are my best friends. My parents are still in Highland Park and each one of our immediate family members is no more than a 15-minute drive from one another. We are extremely close, known to many as the “Pamily.”

As a kid I was physically active and leaned into the creative process more than textbooks. I’m quite certain growing up today I would have been diagnosed with ADD inattentive. I have always been a visual, experiential learner. I was much more interested in creating mixed tapes, studying liner notes on record albums, doodling, and doing jigsaw puzzles rather than homework. I wished that I could retain more of what I had learned but as I got older, I recognized it was not how my brain worked.

With my two sisters, Mom, Grandma, and Bubbe (I’m in the middle)

I went to Boston University’s School of Fine Arts. It was there that I finally studied what I enjoyed. I found a love for sculpture, typography, and photography to name a few. I eventually declared a major and graduated with a BFA in Graphic Design.

I had a love for the East Coast and thought I’d stay but the closeness of my family brought me back to Chicago, a city I love in the summer and curse every winter. I worked in the field of graphic design for several years while satisfying my own creativity by making shower and wedding invitations and birth announcements for friends. I realized at that time while working for an Architecture/Engineering firm that my joy and reward came from my own creativity, instead of what was asked of me by employers.

It was then that I bought my first condo in Chicago. The experience of looking at spaces and homes was something I really enjoyed. The condo I bought was a new conversion, so I was able to make many aesthetic decisions and became close friends with the developer of the project. He encouraged me to take the leap into real estate. It was a difficult decision and one that I remember being afraid to say out loud—that I was going to become a realtor. It seemed to be a strange identity for me. But in 1995, I joined Kahn Realty (soon after purchased by Coldwell Banker) and was awarded Rookie of the Year in sales. It was an interesting niche that I discovered in myself. I loved meeting and helping clients and had a knack for looking at space and exploring wonderful possibilities.

It was at that time I met my husband Danny who had recently moved to Chicago from Atlanta to accept a job in the Industrial Psychology field. We married in August 1998 and I was pregnant with our firstborn in December. The following summer, we moved to the suburbs of Chicago (Glencoe) to start our new family together.

When we moved to Glencoe, I left real estate and stopped working altogether to raise our children. Our son Jesse was born in September 1999. Jason followed in March 2001. When Jason entered first grade and was in school all day, I began working with photographs, paper, and resin. I created custom order art, using old windowpanes and embellishing the photos to capture the essence of the moment. I also created functional art serving trays using paper and typography. My company was called GenuinelyJill and I sold from my website and various shows, including the One of A Kind Show in Chicago.

GenuinelyJill One of A Kind Show booth

For five years, I had a love/hate relationship with resin. When it worked out, it was sleek and beautiful. But it was also toxic, messy, and unpredictable. It also felt very isolating because I was home all day putting a mask on and monitoring the progress of the drying resin for dust and bubbles. And because I was working from my home, I began resenting it more than I was having fun with it.

When I retired GenuinelyJill in 2013, another door opened. I received an email that a company called Tips on Trips and Camps was in search of a Chicago adviser. I was hired by the company to consult with families and find overnight programs for their kids ages 8-18. I loved the idea in the same way I did real estate. It still allowed me to access my creative passions because it was not a 9-5. I could continue to make art while getting out, meeting families (usually other moms), and helping them find a life-changing experience for their child’s summer.

With my consulting partner Julie.


When did you start to think about making a change?

One of the hard parts of this new job, similar to real estate, was responding to the frequent question, “What do you do?” Being creative is a large part of who I am on the inside and somehow my identity felt stifled when telling people I was a consultant rather than an artist.

Although I stressed over the next chapter as my nest was going to be empty in the fall of 2019, the change happened organically. That same year, I found myself stranded in Michigan for an entire snowy day without a car and with a strong desire to create something. Opening cabinets, I found a hole punch and glue. Lots of magazines were in a rack and I began to play. My new medium, hole punch art, was born. I started my first piece, Lady Gaga and finished her a month later. The response from family and friends was immediately positive. I found it to be fun and meditative at the same time. The next piece I created was for my niece for her 21st birthday. I wanted to give her something special and we both are big fans of Ben Platt. So piece number two is Ben. Again, great feedback from everyone and the encouragement to keep going. And so I did.

Lady Gaga


What is your next act?
JillPamArt became a “real thing” in January 2020, when I was 53. Initially I was making pieces for gifts or creating portraits of people who inspire me in order to build a portfolio. Then I started getting requests for commissioned pieces and I felt I was on to something.

When I create them, I try to translate my subject’s essence, heart, and soul, with both the hole punches and the background. I peruse multiple periodicals and rip out and punch holes in the pages. I do it as I go, ripping, then punching about a dozen holes, gluing them and then repeating. I love watching each piece come together. As it evolves, I love it more and more. And it’s such a forgiving medium. If something doesn’t look right to me, I cover it up with more hole punches. I never count the hours it takes because I fear it would stress me out and take away the fun. I also have to take several breaks to stretch and move and give my hands a break.

I charge clients on size rather than time. Typically the hole punch area is 8×10 or 11×14. The background can be any size at all.

At work

I found a wonderful photographer/printer, Bruce Starrenburg,  to create giclee reprints (which use pigment-based inks rather than dye-based inks for a high-quality image on much better paper or wrapped canvas) for me as it was really difficult to let the pieces go that I spent so much time on. I couldn’t believe how equally beautiful the reprints were. They have proved to be my bread and butter thus far as my originals are costly.

Reprints can be as small or large as your wall wants it to be. And with reprints, the customer has the ability to change the background if the current one doesn’t fit the style of their room. It’s fun seeing the details of the hole punches expand on the larger reprints. I also have realized over time that people are not as willing to purchase art during tough times so I have recently begun making functional art. I have put my pieces on a gamut of products from leggings and t-shirts to puzzles and playing cards.

My clients have come from everywhere. When I search my analytics on my website, I can see that they are across the map. I’m still trying to get a handle on how to stay relevant and market myself. I have been fortunate that my business continues to grow but I know it takes a lot of work to maintain that. I recently had a pop-up in my backyard, but I know as the weather changes here I will have to get creative if Covid continues this way.

My pop-up


How supportive were your family and friends?

My family and friends were excited and supportive. Without them, I know I wouldn’t be where I am. It was actually others that ended up giving me the push that brought my business to the next level. A Facebook friend was in the PR business (Ruth Joseph: ruthdjoseph@gmail.com) and took me under her wing because she loved my art. This was February 2020. She had me booked on two local news programs and three newspaper/magazine articles.

With my family


What challenges are you encountering?
The hardest part was building my website and taking the plunge into social media. By nature, I am not a self-promoter and was rarely posting on social media. It felt uncomfortable to suddenly put myself out there. It took me a while to build my own website but I continue to learn and tweak.

The obvious current challenge is Covid. I had my first pop-up show in March and a week later places began to shut down. I had to rely on social media more and self-promotion. That’s a work in progress for me.

I also have to keep up with the business side which means spreadsheets, paperwork, taxes etc… This is not my forte.



What did you learn about yourself through this process? 

I learned the joy I feel in creating something and how much I love sharing that with others. I’m extremely proud of my work and I’ve learned that it’s a powerful thing to be able to say.


Looking back, is there anything you’d have done differently?
I’ve made mistakes but that’s okay. That’s what helps me grow and keeps my brain active and forward thinking.


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

It’s worth it! Life is short, a cliché, I know, but it’s true. Figure it out. It’s worth it. A year ago, I thought, “I wish I’d discovered this earlier.” And then I realized my timing was critical and how nice to have this art to celebrate the good subjects I have chosen. Don’t let ageism deter you because it’s never too early or late to make a difference.

Ruth Bader Ginsberg


What advice do you have for those interested in becoming an artist?

You definitely need another income source. I still consult for Tips on Trips but now call myself an artist rather than consultant. It feels more comfortable on my insides.

While this career path has turned into nearly full time for me, I don’t think any artist is in it for the money. But I’m learning how to create a brand for myself and make it into a business. You need persistence and determination and therefore, you must also love what you’re doing.

Michelle Obama


What resources do you recommend for emerging artists?

There’s been a lot of on the job training for me. I learned how to create my website from Wix and their support is wonderful. I needed to learn about the law and rights of an artist creating images of public figures and I also have had to learn about Illinois law specifically. I found a great attorney, David Adler of Adler Law Group through an organization called Lawyers for the Creative Arts.


Connect with Jill Pam:
Email: JillPamArt@gmail.com
Website: JillPamArt.com
Social media:
Sheridan Road Magazine
ABC 7 News
Glencoe News
Localish Chicago


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. Sandy Rosen

    I enjoyed reading the above on your amazing art medium. I love your talent. I am so happy that your mom sent me your interview! Continued good luck and stay safe!

    • Jill Pam

      Thank you Sandy. I so appreciate your kind words. I hope you and Denny are staying well. Happy holidays to you all.

  2. Loree Sandler

    Congrats, Pam! Your work is fantastic. Fun to watch you evolve.

    • Jill Pam

      Thanks Loree! I really appreciate that. I hope all is well with you and your family!


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