Trueline Spotlight: Two Thumbs Up for Trueline’s Newest Scribe

Reading Time: 4 minutes

When legendary film critic Roger Ebert gave Spike Lee a glowing review for “Do the Right Thing” in 1989, it set the director’s trajectory for decades to come. A chance encounter with Ebert in a Chicago screening room had the same effect on Trueline’s newest writer, Jennifer Shea.

“I was a teenager writing about entertainment as an intern for a local monthly publication called UR Chicago,” Jennifer says. “I saw Roger Ebert a lot at the screening room, but I was too intimidated to approach him—until that fateful afternoon.”

Jennifer, who says she was an awkward-looking teenager with short, spiky black hair, was used to getting a chilly reception when she showed up to cover events. That afternoon, she thought she was running late for a screening, so she was moving hastily down a hallway. She turned a corner and nearly plowed right into Ebert. Instead of chastising Jennifer for a near collision in a corridor, Ebert couldn’t have been nicer.

“He told me the movie I was there to watch was playing a different day,” Jennifer recalls. “He was so nonplussed, kind and accepting. Looking back on it now, I think that was a lesson on how to conduct oneself.”

Other valuable lessons would follow in Jennifer’s early days as a writer, and she draws on those experiences as she continues her writing career with Trueline.

Telling a Story

After moving with family from New York City—where she was born—to Chicago when she was an infant, Jennifer spent several years in the city before moving to the suburbs.

Encouraged by her late grandmother, she took a keen interest in writing, which led to her internship. Though Jennifer says she originally applied to get free tickets to over-18 concerts, writing about Chicago culture was so enjoyable she decided to pursue journalism in college.

Jennifer visiting her mom at her childhood home.

While studying at Scripps College in Claremont, California—Jennifer says she wanted to get out of the Midwest—she wrote for the student newspaper and served as an associate editor. She moved to Austin, Texas, after her junior year, but felt like a fish out of water. So, she headed home.

“I had a fantastic professor at Scripps, Gayle Greene, who taught me a lot about feminism and being a woman who writes for a living and choosing between different priorities in life,” Jennifer recalls.

After working as a waitress and barista for years—Barbara Ehrenreich’s book “Nickel and Dimed” was a big influence during this time—she returned to journalism.

Jennifer reported for community newspapers in Chicago, covered local government for the Niles Bugle and wrote for a newspaper and a magazine in Chicago’s north suburbs. Through it all, she learned how to develop sources and even got a lesson in the business of politics while covering a politician whose dealings weren’t always above board. But her big break in journalism came at the beginning of 2019 with a writing job at the Daily Herald, a suburban Chicago paper that published its first issue in 1871.

“Every assignment was an adventure,” Jennifer says. “The editors were highly skilled, and I learned so much. I remain grateful for the opportunity—especially because it led to Trueline.”

After the pandemic forced cuts at the Herald, including her job, Jennifer found herself working for a nonprofit. But that job involved little writing, and she felt unfulfilled.

Rave Reviews for Trueline

Trueline writers have unique experiences, but they all share at least one thing in common: a love of writing. When she came across the job listing for a writing position, Jennifer says she applied and was pleasantly surprised when she heard from Joy Wilkie, the company’s director of people and culture. She interviewed with Joy and members of the writing staff.

“I had a good feeling about the team after our conversations. They were genuine,” Jennifer says.

An admitted introvert, Jennifer says she came to terms with the social nature of writing during her Chicago reporting days.

Jennifer and one of her two cats, Leia.

“Someone at a crowded meeting once pointed out there was a reporter in attendance, and it made me want to crawl into a hole,” Jennifer remembers. “But I love writing and telling stories so much that I forget to be shy.”

When she’s not writing features and abstracts for Trueline—and connecting with people she says are wonderful and fun—she spends her weekends as a freelance writer.

“These days, it is a real privilege to write for a living,” she says.


Did you know? Jennifer once broke her arm playing soccer, a game known for leg and foot work, and she is a member of the Yelp Elite Squad, a dorky way that Yelp recognizes prolific contributors. She shares a birthday—May 7—with the actors Breckin Meyer, Aidy Bryant and Gary Cooper, the humanitarian Eva Perón and Tchaikovsky.

Who’d play you in a movie about you? Laura Donnelly

Bucket list: To dine at every decent vegan restaurant in Chicago and to visit Indiana Dunes National Park in Indiana.

Greatest achievement so far: Professionally, the stories at the Herald that required few edits. Personally, raising two rescue cats from kittenhood to adulthood (Amelia and Leia).