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Becoming a Contemporary Fine Artist in Midlife: Katherine’s Story

Published on 12/11/2017

When her daughters entered middle school, Katherine considered returning to practicing law or delving into her lifelong passion for art. She chose to honor her artistic calling and is now a fine artist, with a focus on oil painting.


Tell us a little about your background…
I grew up in New Jersey, the second of five siblings. Living near Philadelphia and New York was a great advantage for me because I had an early exposure to a lot of great art resources. On weekends, we would often end up on various cultural outings including visiting the Philadelphia Museum of Art, where I developed my love of painting, and Brandywine, where I admired the artwork of the Wyeth family. We also spent time in New York City, where we frequently went to all of the major museums, including the Metropolitan Museum of Art—little did I know then that I would be chosen to be a copyist at the Met. I remember falling in love with the works of the Hudson River School painters as well as the Ashcan school. I was also inspired by my great-aunt, Peggy Merrick, an established painter and pastel artist, who encouraged me to pursue my artistic interests.

My father was an American Literature College professor and we spent our summers traveling all over the country visiting the literary homes of famous writers. I was a History Major at Duke University but still took advantage of the emerging art department there, taking drawing and painting classes. After college, I moved to Europe with the Council on Educational Exchange, which enabled me to get a work permit in England. I worked in Central London in a major advertising agency and spent many a lunch hour in the National Portrait Gallery studying the artwork. After London, I moved to Florence, Italy where I was in heaven among all the Florentine museums while I studied Italian.

Living in Italy (1986)

Living in Italy (1986)

After several years in Europe, I returned to the US and started working in NYC, first in advertising and eventually as a paralegal in a very small law firm specializing in arts-related not-for-profit clients, including numerous dance troops, visual artists, and literary foundations. One of our clients was a young, German figurative painter who lived in a penthouse near Tompkins Square Park. Visiting his studio and attending to his mundane legal issues such as unpaid parking tickets, I found I was drawn instead to his massive, expressionist paintings. I remember being very intrigued. When he asked my opinion about a color he was considering, I realized I loved painting—this was my ah-hah moment. However, equally intrigued by my legal work with such interesting clients, I decided to pursue law, the more traditional option, at this point in my life. Still, in my early twenties, I also needed a steady income, which the law had the potential to provide.

At this point, I met my wonderful husband, a commodities trader and Yale grad in NYC and we eventually married and had two beautiful daughters. After law school, I practiced law first in a Japanese law firm and ultimately in a smaller boutique firm concentrating on trademark registrations and prosecutions. 

When did you start to think about making a change?
I stopped practicing law to raise my children. Even while pregnant with my first (who is now 19), I joined a small local art group and painted once a week. When my daughters were in middle school, I started thinking more about what I wanted to do. I considered either returning to the practice of law or further delving into my artistic side. I began attending programs by the Volunteer Lawyers for the Arts in NYC about starting your own for-profit art business. I found these incredibly helpful and eye-opening as they asked questions such as where do you see yourself in five years/ten years etc. (It was interesting to look at my answers five years later and realize I had attained many of my goals).

 What is your next act?
I am now a Contemporary Fine Artist specializing in realistic landscape oil painting. I launched my business in my early fifties. My work is exhibited online at Katherine Jennings Fine Art and in numerous galleries through juried shows. I am constantly looking for new opportunities to exhibit my work. During 2017, I have shown my paintings in the Upstream Gallery in Hastings on Hudson, New York as well as in the Lyme Art Association in Old Lyme, Connecticut, where I am an Associate Artist. This past summer, I was chosen to participate in an International Juried Show, “Playing with Perspective,” at the East End Arts Gallery in Riverhead, New York.

I am a Juried Member of a national art group for oil painters called OPA (the Oil Painters of America). And I was recently selected to be in the 2017 Spring Semester of the Copyist Program at the Metropolitan Museum of Art, where I had the privilege of spending eight weeks doing an intensive copy of a masterpiece of my choice. I chose “Ernesta (with Nurse)” by the American Society Portraitist, Cecilia Beaux, because I have always greatly admired the painting and was challenged by the opportunity to paint the various whites depicted in the dresses. To be in that setting in such close proximity to a great piece of art was a truly memorable experience.

I just took on a part-time job as a Development Associate (Capital Campaign and Major Gifts) at the Edward Hopper House.  I have always admired him as a painter and suddenly I saw this part-time job come up, based at his childhood home in Nyack. They are in the midst of rechartering into a museum and are hoping to expand their reach. Finally, I also got into a really great art show for professional women artists at the National Arts Club in Gramercy Park in New York City (learn more here). The opening is January 19, 2018, and benefits the Metropolitan Museum of Art.


Why did you choose this next act and how did you prepare?
I have always been interested in both art and law and starting my own art business seemed to be a good outlet for my talent and passion. Having already worked in NYC in several law firms, it seemed like a good time to give my passion for art a chance.

I began by taking as many classes and workshops as I could. Being around other artists and having input from a knowledgeable instructor is priceless. I studied under the talented artist and instructor, Gary Godbee at the Yard School of Art at the Montclair Art Museum; under his tutelage, I have developed and furthered my artistic skills. He has definitely brought me to another level and pushes me to go even further. Through his class, I met many talented emerging artists and have developed a group of female artist friends. We travel to various art exhibits together and recently spent a day at the Met touring with one of the women, who is also a curator at the museum.

Traveling with artist friends

Traveling with artist friends

How supportive were your family and friends?
My family and friends were incredibly supportive. My husband, in particular, has supported me throughout the process. I remember doing a show with a fellow artist and as she watched my husband helping hang the art, she mentioned how impressed she was that he really seemed to care and made sure each frame was straight.

My children have supported me by helping me set up shows and even provided some welcome constructive criticism. I also have one friend in particular, a fellow artist, Dana DiMuro, who introduced me to a lot of art resources and encouraged me to go to workshops with her. We have traveled to Northern California, Vermont, Virginia, Philadelphia, and New York City to take various workshops together. One of our most memorable trips was studying with Jeanette Le Grue in Northern California and staying in Bodega Bay at the restaurant/hotel where Alfred Hitchcock’s The Birds was filmed (Inn at the Tides). The location lived up to its name. We awoke each morning to a deep enveloping fog that quickly dissipated as we made our way to the workshop site, where we painted “en plein air” at a typical northern California farm with a white barn.

With Dana in Bodega Bay

With Dana in Bodega Bay

What challenges do you encounter?
You definitely have to have a thick skin to be an artist because you are accepted into some Juried Shows while you are rejected by others. But it is worth it. I was accepted into the first Juried show I entered, which was a nice start. I also had my work validated when I received second place in the prestigious Caldwell Art Fair in 2010. Finally, I remember how elated I was when I had a piece accepted into the esteemed Lyme Art Association “American Waters: A Marine Art Exhibition” and the piece sold before the show even opened.

Painting can be very grueling and the constant exposure to chemicals can be worrisome. But there is a reward for being immersed in the creative process that is almost indescribable. I find that if I am really involved in executing a painting of something I love that the picture seems to just fly out of me. I enjoy that first attempt when you are loose and free to express the general idea. With oil paint, you can usually correct yourself later without any ramifications.  Sometimes though the paint gets too thick and a painting can be ruined. I also try to constantly research new venues and outlets on the internet; this keeps me motivated and engaged in the constantly changing art market.

What have you learned about yourself through this process?
I have learned that my “passion” truly is oil painting and that I love being a creative person. At some point in the process, I realized that I truly am an “artist,” no matter how pretentious that label sounds. I also discovered that I enjoy sharing my love of art through teaching. I have instilled my passion in my daughters and it is so gratifying to see them engaging in the arts. One of my daughters will be starting a job in an art gallery and the other has been accepted into the Frick Museum in NYC for an intensive high school study program.

Painting "en plein air" north of San Francisco

Painting “en plein air” north of San Francisco

Looking back, is there anything you’d have done differently?
I was a History major at Duke and I often look back and think I should have majored in at least Art History. But I NEVER regret my liberal arts education. Although I’m sure I would have loved going to a fine art school, I’m thankful that I also have my “lawyer” side. My background in law has been incredibly helpful in navigating the business of art.


What advice do you have for women seeking reinvention in midlife, and possibly a passion for art?
I truly believe that you will be happiest when you are doing something that you feel “passionate” about. Some people have trouble figuring out what that is but for me, it was pretty clear from an early age.

If you’re interested in pursuing art, network and join as many art groups as possible. Take classes and constantly learn new things. I believe you will develop your own artistic style by synthesizing what you learn from many different teachers. Each teacher has something different to offer and it is a constant learning process. I continue to attend art classes as well as legal classes about art. There is a fabulous group called The Center for Art Law in Brooklyn that deals with legal issues in art matters. I recently became a contributing author for their online newsletter and submitted a piece on the effect of current immigration policies on immigrant artists.

I also recommend finding a place you can establish as your studio. I went through the process of renting various art studios and ended up ultimately making my own in my house. While I miss the camaraderie of other artists, the convenience outweighs any isolation I might feel.

My studio

My studio

Take a chance and apply to Juried Art shows and join local art associations so that you are aware of open calls. Keep trying. You will face rejections and acceptances both. There are so many opportunities out there.

Visit galleries, make contacts, take workshops, and make yourself known. Most recently I was planning on traveling to San Diego to visit my daughter in college and I found a MeetUp group online (the San Diego En Plein Air Painters) and spent several glorious days painting on the cliffs of La Jolla overlooking the Pacific Ocean.

What resources do you recommend?
I realized I would not be taken seriously unless I had a website so I set one up through FASO (Fine Art Studio Online). I now have my own website where I sell my art online. Of course, in order to put images of my artwork online, I needed to learn how to photograph them properly, which entailed taking a course in that. The Silvermine Arts Center in New Canaan, CT and the Montclair art Museum were invaluable in that regard.

Join national organizations such as Oil Painters of America (OPA).

One particularly helpful book is The Artist’s Guide: How to Make a Living Doing What You Love by Jackie Battenfield.

Excellent places to take classes in the New York City area include National Academy of Art (I studied under Dan Gheno), Art Students League, Montclair Art Museum, Ridgewood Art Institute, Visual Arts Center of New Jersey (I studied under Anne Kullaf), The Florence Academy of Art in Jersey City, West St. Studios in Greenpoint, Brooklyn (I studied under Jennifer Gennari).

New York Foundation on the Arts is an excellent source of information about recent events and artist opportunities.

Juried Art Services is also a good website for finding new opportunities.

I am an Associate Member of The Lyme Art Association in Old Lyme, Connecticut, and have been in numerous exhibits there. I am about to participate in their En Plein Air event to showcase the beauty of Old Lyme. Studio Montclair, a local art organization in the NYC metro area, is a wonderful organization.

There are a plethora of art tutorials available online at no cost, that are very good and informative. Artists I particularly enjoy following on Facebook and Instagram are Rob Liberace and Marc Dallesio. 

What’s next for you?
I hope to narrow and develop my focus in my art so that I will become known for a particular artistic style. Landscape painting in oil, both “en plein air” and in my studio, is my passion. I have recently been asked to submit a portfolio of paintings that are much larger in size than my usual works and I am looking forward to the challenge. I would also like to simultaneously do some legal writing about art issues in the law and get more involved in art advocacy groups. I am trained as a Mediator in Art Law so I would like to put that to use.


Connect with Katherine Y. Jennings
Email: kjfineartwork@gmail.com
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Facebook Page
Instagram: kathjennings4

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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