



This month I’ve been painting a group of portraits of my family. I started with myself, then my husband, and finally our son. It’s been an interesting practice to notice how the experience of painting each one of us changes. For my portrait and my husband’s I worked from life: looking into a mirror for mine and asking my partner to pose for his. One of the challenges of working from life is needing to translate a three-dimensional thing into the two dimensions of a painting.
For my son’s portrait, rather than asking him to pose for hours, I opted to work from a photo instead. While it’s easier – in a way – to work from a photo because the camera does the work of flattening life’s three dimensions into two, it’s also easy to become obsessive about EVERY SINGLE DETAIL. This isn’t necessarily a good thing when painting. Part of painting is learning to discern which details to include and how much to leave out. The longer we stare at our subject, the more we discover. And if we include every little thing, the result will surprisingly look less realistic because of how our eyes and brains perceive what we see in real life. For example, if I paint an area in shadow with the same degree of detail and contrast as a part in the light, something will seem off when we look at the painting. For the spatial effect to work, we actually have to lessen the contrast and level of detail in the shadows.
Another part of what makes painting so interesting and complicated is the making of decisions of how to portray something or someone in a way that reveals an aspect of them and/or of the artist. It is an interesting challenge to make a realistic image that still looks like a painting rather than trying to make it look like a photo, which is more of an exercise in copying.

There’s also something magical about seeing an image in a painting, and then as you step closer to the work, gradually realizing that the image is just a collection of brush marks. (Have I mentioned that I often get into trouble in museums when I get a little too close to paintings?)
Here’s a collection of images showing the process of making the portrait of my son, from start to finish:









This week I made a portrait of my husband Tim. Since I made a self-portrait a couple weeks ago, I decided to make a trio of portraits that include our son too. Below are images of the process of day 1 and day 2. I’m really enjoying painting these at this scale. It was also fun to recreate one of my paintings in the background of this one.



Also this week I came across this photo of Frida Kahlo and Diego Rivera watching a solar eclipse with friends in 1932.
And I learned about about “Andrea Y. Motley Crabtree—the first woman to pass the rigorous U.S. Army test for deep sea diving, a highly specialized aspect of military service,” when I saw this portrait of her at the Met museum.
My family had planned to go backpacking last weekend, and I spent the week trying to figure out just the right spot for us: the right distance, difficulty, and weather conditions. A mellow option on Commissary Ridge and up to Mount Mitchell? A strenuous hike over six of the tallest mountains on the East Coast? Or The Seven Sisters, a tough hike near Montreat? By dinner time Friday night, with the predicted weekend weather in the mountains much colder than we’d expected, we decided to cancel our plans and go backpacking at another (warmer) time. Our son is only 11 years old, and while he enjoys backpacking, we want to keep it fun for him. Being out in the elements and cold all weekend didn’t sound like fun.
After all that anticipation though, I was mentally prepared to do something epic. A cycling friend proposed an 80-miler with a big climb on Saturday – perfect! So with some sun and temps in the 50’s and 60’s, a group of us headed out toward Stone Mountain and climbed Oklahoma, a nasty 3-mile long climb with an average grade of 6% and some super steep pitches toward the top. What’s special about this though is that I haven’t had the desire to put in big miles on the bike in a few years. It felt good to want to do that, and although I haven’t put in the on-bike training I would have preferred before a ride like this, I have been doing some long hikes this year. It turns out that the long miles on foot coupled with some short hard rides were enough to be able to complete the 80 miles and feel recovered enough to ride a relaxed 45 miles the next day.
I think what helped a lot was that after over two decades of riding my bike, I have finally learned how to properly fuel up for sustained energy. Marathon training and lots of hiking helped me by learning to rely on more real food rather than “performance” food (bars, gels, and the like).

Sunday was Mother’s Day, and we celebrated with a picnic in one of our favorite spots. We went for a walk afterward and spotted beavers! We stayed for a while spying on them and watching as they silently swam down the creek and made their way over and under fallen logs. They are surprisingly big! On the way out of the woods, I noticed some interesting shapes, textures, and colors around us, and planned to come back with my sketchbook. There seemed to be lots of possibilities for abstraction.

That evening while our son was playing with his Nerf gun, he shot a dart at one of my 6-foot tall paintings in the living room. I’m happy to say the painting survived.
The next day, sketchbook and watercolors in tow, I set up a little camp chair to make some drawings. I made a few thumbnail sketches and color studies, then watched ducks darting around and geese as they strolled with their little ones.

A small group of my paintings is on view at the Forsyth County Central Library in Winston-Salem until the end of June. I love that while they’re installed on the second floor, they are visible through a glass wall as soon as you walk in from the ground level. It’s nice to have multiple vantage points like that. The library is located at 660 W. 5th St.
The work is available for purchase here.

I’m relaunching coaching and mentoring for artists, and I’ve opened up time slots for one-on-one sessions. During these sessions, we’ll work on whatever you feel needs attention: whether that’s feedback on a project, helping you figure out what’s next, getting unstuck and taking steps to establish an art practice you can maintain, how to get your work out in the world, or whatever other art-related things have come up for you.
For those of you who don’t know me, I’m a working artist and I teach art in higher ed. I finished my MFA back in 2004, and after a circuitous route during which I taught art, worked as a guide in adventure travel and taught yoga, I have found ways to raise a family, work a day job, be an outdoor athlete, and keep up my artistic practice. If you want to know more about what I’ve been up to art-wise in the last 20+ years, you can look at my resumé.
If you’re interested in coaching/mentoring, you can book a session here https://jessicasingerman.com/coaching-and-mentoring/
And here is a tiny art installation for Legos because many tiny steps can amount to big things. And also because I love Legos.

I recently had the chance to chat with Bold Journey, and the interview is live! We talk about challenges, self-care, and the skills to focus on for success.
You can read the interview here.

I think making self portraits is a good practice as an artist. It serves as a benchmark to gauge skill and changing concerns in technique and color. Rembrandt famously made 100 self portraits (that we know of), and it’s interesting to notice the changes in techniques and age in each one.
The last couple days I painted a self portrait, and I think it’s finished. It’s oil on wood and measures 12×12 inches.
In the next few weeks as classes wind down this semester, I’m reintroducing coaching for artists. This will be in a new format, and you’ll be able to easily book coaching calls here. If you know an artist who’s feeling creatively stuck or needs some art-related guidance, can you let them know?


It’s that time of year… the weather is getting warmer, the bike rides are getting faster, and the end of the school year is in sight! With the spring semester winding down soon, my schedule will open up for commissions again. This spring I will be available for 1-2 commissioned projects.
The surfers, skiers, and sprinter paintings below are three commissioned paintings I made for a friend a few years ago. I really enjoyed making these – not only because they all feature athletes, but also because I could play with the elements of paintings that I really dig: surprising colors, juicy paint, and big bold shapes.
Check out my commissions page to learn more about the process of making custom artwork and to see other commissioned paintings I’ve made in the past. And email me if this sounds interesting to you. Cheers!



A couple of weeks ago I gave a talk at The Art Gallery at Congdon Yards. We talked about my background, inspiration, processes, and techniques, and the group had some great questions. The gallery was kind enough to film the event and make a video, and you can watch the talk and Q&A below.
My artwork is on display there during my exhibition entitled A Place of Leaves and Earth from Jan. 25 – April 19.