Successful Wom*n: Executive Director and Founder of Art With A Heart, Randi Pupkin

Randi Pupkin is Executive Director and Founder of Art With A Heart, a visual arts organization in Baltimore, MD that takes art programs into the community: schools, shelters, group homes, community centers, recreation centers, hospitals, and senior facilities. She believes in the power of art as an important part of normal human growth and development from the ages of 2 to 102. Randi shares with us her success story, from successful lawyer with her own practice to pounding the pavement in Baltimore communities, bringing art classes out of the trunk of her car, we learn from Randi how we can find our purpose and make dreams a reality.


Tell us about your earlier life. Where did you grow up?

I was born and raised in Baltimore. My father and my grandfather were tailors in West Baltimore and they made custom-made suits, mostly for athletes and politicians. I am a child of the civil rights movement here in 1968. I was six years old and I remember the riots in Baltimore. I had an African-American nanny who was my compass on life. She was more a mother to me than my mother and during the riots we took a ride, my father put me in the back of his car and this is when people were basically afraid to go out and we drove by a swim club that was near our house and people were protesting that they didn’t want any blacks allowed in the swim club and I instantly connected to my nanny and wanted to cross out all of their signs with my crayons. I really believe that moment in my life, seeing those people and that hate, that moment changed my life forever and the trajectory that I would take in my life.

So I decided that I was going to change the world that day and then by the time I was about eight I decided I was going to do it by being a lawyer and followed that dream until I became a lawyer. I wasn’t a great student but I was more a student of life than I was a student of academics, but then I realized if I wanted to get into law school, I had to do life and academics so I started a little harder in college, I went to a small liberal college called Lynchburg College in Virginia and that too was an interesting experience for me because it was a college that was based on the disciples of Christ and I’m Jewish so there were six Jewish people at that school and that impacted me as well. I’ve always been culturally Jewish but not academically or very religious, just more spiritually culturally Jewish but being in an environment where there’s nobody like you which kind of goes back to the whole civil rights movement, it impacts your life in ways moving forward. So studied there, came back to Baltimore and went to law school here. I am the first college graduate in my family. I have an older sister and my parents got divorced when I was in third grade. I want to indicate that my mother left my father for a married man when I was in third grade so this whole package, a lot of students think I was raised in privilege, but I had a pretty crazy childhood. Women did not leave men in those years, this was the 70s, so she left my father for a married man and he never left his wife for 26 years and I watched my mother in a lot of pain but I never really felt sorry for her. We make our life choices, but he was like a dad to me because my father was so damaged by the whole thing that he really didn’t see my sister and me. So my sister and I were raised by this single mother who was very busy doing her own life and my nanny who would sleep over when my mother wasn’t at home.

How long were you a lawyer?

Fourteen years. My first job was with a corporation called Fidelity and Deposit Company. I didn’t even last a year and it was a lot of fun but I felt like I was still in college , so I got [another] job and it was three male partners Schilling, Black, and Baker and Ruben. Schilling was very old well respected, seersucker suit, To Kill a Mockingbird’s, Atticus Finch, a dying breed of lawyer and I learned a lot from him and I was placed with an attorney named Tom Baker. I wound up doing construction litigation because that’s what he did. The lawyer who was like Atticus Finch just ironically represented the guy that my mother had dated for 26 years, like handled his estates and trust. So every now and then even when they weren’t together anymore and my mother is married to another man now, I still ended up seeing him from time to time.

Do you feel like you were making change you wanted to make when you were a lawyer?

I felt like I was learning and I felt like I was helping people. I feel like I was a good lawyer, I was very dedicated to my clients, I gave every case everything so it didn’t matter if it was $1 million case it was the same to me as if it was a $20,000 case and I prepared for a lot both and my boss was the kind of guy that just threw you to the wolves and would say “OK next week you’re trying this case”. So my first trial was against Kevin Kamenetz who is now the city council president for Baltimore County and I beat him and then I let him know it was my first trial.

But there were these times that I had these epiphanies. I had kids at that time, after seven years of working in the firm for this partner, I had my daughter and I actually left the firm and started my own firm. Six weeks postpartum, I decided I was going to open my own practice and nobody said to me maybe you’re just being a little hormonal. This is just what I did. It was successful for another seven years until I started Art With A Heart. After I left the firm clients came with me and I grew another construction practice and it’s in the last seven years that I would be like, “is this really the rest of my life?” and then one day I had a phone call with an attorney and I hung up the phone from him after this really contentious conversation and I had like oh my god this is my life. This beige life. The office was beige, the carpet was beige, the folders were beige, it was all beige and I was fighting with this lawyer who is a jerk and this is chapter 5 and 25 is the same thing. Who even wants to read this beige book? It’s boring and it’s ridiculous. So I went home from work and I said to my husband “I have got to make a change”. This job is making me a witch. I had two small children and I’d be yelling at lawyers on the car phone and I thought if I’m going to yell I wanted to be for something really great and meaningful so I slowly incorporated Art with a Heart from my desk in my law office and started just pounding the pavement and talking to people, [asking] do you think this is a good idea? Bringing art into the community as opposed to building a studio or something. When I was a little girl, I went to this studio called Mary’s Art Studio but I started to research the city and first of all there’s no studios in the communities that I was thinking of servicing and even if there were, nobody could drive them to a place to get the art. Then I started learning a lot but that the core was that I would bring Mary’s Art Studio into the community and if they liked it, we’d stay for 12 weeks then we’d go back. These were all just ideas but I started with incorporating and talking to people and getting some validation that it was a good idea, and never asked anybody if they’d fund it.


Why from lawyer to art?

I always had a passion for art and I will tell you in talking to you I can relate to the students in our programs because I explained a little bit of my childhood, which I never really talk about that piece of my childhood when I share the story, but really art was probably for me my escape from all of the craziness that was around me and I always say why art? It’s because art let’s you go anywhere you want and I guess at that time I really wanted to go somewhere else. I was very interested in drawing cartoons and I started to see everything with dark black lines like a cartoon so that’s why because I felt like my love of art and my love of what art allows a person to feel and do and I love people and so I just combined both of my loves and founded this organization based on that. Being in a room with people but creatively working on something so that you can feel safe and nurtured by the people around you while everybody’s working on their own thing or you could be talking and solving the world’s problems. It really gives you the opportunity to do anything and so many children never have the opportunity to imagine and explore anything outside of their one block radius, so I hope that we’re giving them an opportunity. It certainly gave it to me.

What was the most best thing that happened when you were starting Art With A Heart?

The validation of the work. Having little kids say, “the art lady is here!” and also the amount of the connections I was making in communities and with people that I otherwise would never ever happen upon but for starting this organization. That was pretty exciting to me and it also cost a few friend divorces because I really was changing and becoming more aware of no matter how difficult I think my life could be, I know people far more vulnerable and so I used to say that I was meeting angels on earth. I was meeting people doing God’s work but doing work that was just amazing and their determination was admirable and while I might’ve been in the thick of that I never saw myself that way. I loved that and I still love meeting people that are really authentically committed to community and some people are not authentically committed but I think you can spot them on social media.

What was the most difficult part in starting Art With A Heart?

The most difficult part, surprisingly was not taking the leap of faith. I’m a risk taker and I think every successful woman, every successful person really, has to take a risk to get success. You’ll hear a story from a woman who started a business that didn’t jump off a cliff and later check to see if they were wearing a parachute. I’ve jumped off the cliff so many times not sure if I’m wearing a parachute. This space that we’re sitting in is a cliff and I had to do it. So the hardest thing was not jumping off the cliff for me, it wasn’t immediate. There were little immediate things like I never taught. I never wrote curriculum. The hardest thing at the beginning was really balancing my law practice, my children, my dog, my husband and starting a new business that was really challenging. So I was doing law by day, throwing dinner on the table, and then doing art classes that I had to plan for and buy supplies for at night. I started the process of getting a nonprofit status and to get your nonprofit status you can’t just have an idea, you have to have a working program and I didn’t know that, so I had my law practice and I had to go to work. My first sites were a group home for emotionally troubled boys, an Alzheimer’s facility, and House of Ruth of Maryland. So those were the first four sites.

Describe your first class.

House of Ruth was moms and kids and we had two-year-olds and their parents and I have like some very vivid memories of the House of Ruth at the very beginning. I was never afraid to do anything. I would just do anything because I was that stupid and so when there were really little kids I’d give them little cups of water and they would paint with water but the parents would paint and we would talk about an artist. All the paint was in my shed and I had a Dodge Durango filled to the gills in the back with paint that would freeze in the car and I would take a boombox and play music while they did the art and I’ll never forget it at the very beginning there was a time where I Will Survive came on the music and all the women started singing. This is a shelter and it was one of those moments ingrained in my memory from there and then we would hang all the art in the House of Ruth. They didn’t have anything on the walls and we hung all the art and it just it was really special and the kids were really excited about us coming.

And then two group homes for emotionally troubled boys. I’ll never forget my first night there. I had worked all day as a lawyer, probably served my family canned string beans for dinner and went to these group homes. I walked into this group home and they lead me into this dark basement with no windows and eight African-American boys, all who had no interest in art, and some of them indulged me and did the art, some of them were completely off their rockers and did the art then ripped it up in my face and called me a racist bitch and I’m sitting thinking I’m not getting paid to do this. I just worked all day long. I’m so not a racist bitch. I got in my car, called my husband and I said if I was less of a human being I would never go back but next week I went back at the same time.


How would you define success in your life? What advice would you give another woman?

Success for me is being proud of what you’re doing. I think having a sense of pride in what you do is really important to success. You can be a great lawyer and hate it. So you could be considered a successful lawyer and be miserable in your life. To me that’s not success. This is hard work but I’m really proud of it. I find that anything worth having is hard work and if anybody says otherwise, I don’t think they’re right. I honestly don’t think anything in life that’s worth anything comes easy. Children are not easy, they’re hard work so for me success is dedicating yourself to something and being proud of what it is after you’ve dedicated yourself to it. So I feel like this is successful. Also, a lot of people talk about their families and I don’t want to neglect that because ultimately my legacy is my family and how they prosper because of the things that I’ve done so I hope that my family and my children will be good people and will understand finding joy in your work is an important part of being a happy and healthy human being. I hope that for all of the children we serve, actually.

There’s always this component of my family and children are adults now.They have to take what they seen and learned and fly with it. I can no longer be responsible for that so I don’t always include it in my conversation. I do think a partnership like my marriage is a part of it. I never could have done this without a supportive and loving husband. He married a lawyer who was making money who decided to give that up and make no money for a long time. So, I would say a lot of that to other women about success. I think success is about meeting your purpose and knowing your purpose and I’m not saying 365 days a year you wake up and you’re this cheerleader for your purpose, but I think when you know your purpose you can work to be successful.

Learn more about Art With A Heart at

All images © Rachel King, 2018


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