Former Senate staffer paints a new future as an artist

Once a Senate staffer, Diana Naylor is painting a new path for herself, leaving Capitol Hill to become an artist.

Naylor said she never envisioned leaving Washington when she first moved there after college in 2016 and started an internship with Rep. Scott Peters (D-Calif.).

She went on to become Sen. Tom Carper’s (D-Del.) director of scheduling before working for the hedge fund Citadel.

In 2021, with much of the country staying at home amid the COVID-19 pandemic, boredom — and some artistic inspiration — struck.

“I was driving by an art store and I was like, ‘I’m bored. I’m in lockdown. Why don’t I just pick up some supplies?’” Naylor, 31, recalled.

“I had never painted. I had never done anything creative,” the Arizona State University grad said. “I was more focused on being a political wonk than I was being an artist.”

But after picking up a paintbrush, the political wonk was hooked.

“Now my apartment is filled with massive canvases and I’m dedicating everything I have to being a full-time artist,” said Naylor, who moved to New York City as she sketched out her career switch.

She describes her artwork as contemporary: “It’s intended to evoke positivity and also challenge at the same time. You look at it and it looks very simple, but there’s always this underlying meaning and a process behind it.”

“I think that was something that I really pulled from my D.C. days, is the love of a process,” Naylor said.

“Working on the Hill is the most bureaucratic place, but everything works because of that when you’re looking at the legislative process,” she explained.

“At the end of the day, you could see a bill that is 100 pages, and it looks pretty straightforward, but you don’t see all the work that goes in behind it. And I feel like my paintings are reflective of that as well, where it’s like you see the end product, but behind that there’s this really creative, problem-solving lens that has to go into the work before it can actually come to fruition.”

Since officially launching her art career less than two months ago, Naylor’s sold four of her paintings. She also partnered with stemware company Glasvin, which selected her art to be showcased across its products beginning next year.

Naylor said she realized, looking back on her job in Washington, that her role at the Capitol helped spur her newfound passion, when she’d often admire the priceless pieces of art adorning the walls.

“Whenever Sen. Carper was voting, I was like, ‘Alright, you go vote. I’m gonna go take a lap [around the Capitol], and go appreciate the halls and this will be like my mental reprieve.’”

It would be a “dream” to have her art one day hang in the very same halls of the Capitol that she used to roam, she said.

Carper praised his former staffer-turned-painter in a statement to ITK.

“Diana pours her passion into everything she does and thrives in unchartered territories,” Carper said. “She holds her work to a very high standard, and I have no doubt she will see continued success in this new chapter.”

Asked whether the art world or politics was harder to break into, Naylor, who grew up in Annapolis, Md., said she’s faced a greater challenge making her mark in the creative community.

“In D.C., I feel like you always feel like the dumbest person in the room. At least I did, because everyone there is so smart. Whereas in the art world, everyone is also so smart, but they’re also creative, and matching that is extremely hard to do.”

“It’s kind of like running for office — you have to be in the right place at the right time,” she said of taking a leap of faith and jumping from politics to art.

“Everybody has their moment, and if you miss your moment, your moment doesn’t come again.”

—Updated at 11:09 a.m.