“I had stretched myself thin. Should I just stick to what I know and be okay with who I am?"

I felt an urge to document the pandemic by making a painting with someone wearing a mask. Inspired by a TED talk about the stories that light our path forward in uncertain times, I showed some of my portraits to my Lead Now Pittsburgh cohort and invited them to let me know if they were interested in being painted. Evaine volunteered.

On the second of two walks along the North Shore, Evaine and I came upon this groove of young saplings. Evaine was concerned about the health of the trees and ran over to inspect one. Her inquisitive one-eyed squint felt like it revealed something personal, like she was looking inside herself, ready to break free.

Evaine has always been a warrior for nature, and in this moment she became nature. She became the tree. Her floral print mask and wool sweater blend and swirl into the patterns of leaves, vines and branches surrounding and supporting her. I purchased new plant-based oil paints to intensify the colors of this painting. I wanted it to glow. I wanted the inner light to be undeniable.

It looks like a photo to me. Of the paintings that Jeffrey did in this series, not that it’s not beautiful, but it’s a very natural picture and setting and very realistic portrayal of myself, versus beautifying someone. It feels very real. My facial expression and the look of skepticism on my face is fairly common. It’s very real.

That’s along the Allegheny River Trail, along the North Side. And some group had cleared a lot of the invasive species in that area and planted some new saplings for trees. And then those are protective for new planting.

You can see in the background some of the other trees are popping out of those tubes. Those tubes are not supposed to be left on for very long. They’re supposed to be on long enough that they’re established and animals can’t get to them. But at some point you have to remove them so the tree can breathe. So why I was looking was that it looked like there was a lot of moisture in there and I was like, is this rotting inside? And that was what I was trying to figure out. So I actually don’t know if that’s alive or not. We were in a leadership program which was aimed at executive directors and leaders in nonprofit sector. I was actually ousted from my organization without cause or explanation on a random Tuesday afternoon. So, a bit of a shock and certainly a blow to my… to everything—to my ego, my plans, my belief in some things.

Jeffrey was introducing this project and saying, “I think I wanna do something with this. Would other people be willing to be one of the subjects?” And I immediately raised my hand. Without knowing really what had happened and what my reputation was gonna be like, so wanting to be a part of it to have that relevance and have a sense of importance and belonging.

For my wedding photos, which is like twenty years ago now, I went and did the whole makeup trial and all of that and they did several hairstyles and they looked fancy and special and I was like, “This is isn’t me.” And they did really heavy makeup and I was like, “I don’t even really wear makeup.” And so I was like, “When I take my wedding photos, and I look at them however many years later, I want it to look like me. Not like, wow, what happened to you?” So I think that whole mind journey has occurred. You’ve got that split second of, “I could look prettier,” but at the same time, like, “This is who I am.”

I remember it was cold, and I have a man’s sweater and I just pulled my hair back and I’m wearing a mask, and not that I didn’t care, but it was a different sense of importance. That was not really what was important. It was just a different mentality.

Through that experience of being fired and being in that program and everything that’s happened since, I think there’s just a sense of—for so many years as an executive director and with all those responsibilities of managing a team and pleasing funders and, partners and all of those things—just a realization of how much I had stretched myself thin to meet all those different needs. It was draining. So even though I could do it, there were these moments of, “Should I have been doing that in the first place, and should I just stick to what I know and be okay with who I am? And the people that want to be around me will find me. And you know, the rest don’t, not that they don’t matter, but they don’t matter.” So, that was a good time for that bit of growth.

My name is Dr. Evaine Kim Sing, and I feel grateful that you have the opportunity to look at this painting and see me at a time when I didn’t know what I would be.