Chicago artist Phineas X. Jones finds an audience for illustrated optimism

Chicago illustrator Phineas X. Jones has built an ongoing art project around a modest possibility: “Maybe It Will Happen Today.” Since posting his first illustration in the series on March 20, 2025, he has created more than 200 versions and drawn an audience of roughly 12,000 followers on Bluesky.

The words stay the same, but their surroundings change considerably. Jones has incorporated them into imagery inspired by illuminated manuscripts, a Wheel of Fortune puzzle board, Federal Art Project woodcuts and René Magritte. Other illustrations feature recognizable characters such as Paddington Bear or a Chicago paletero, giving viewers many different ways into the same open-ended idea.

Jones deliberately leaves the meaning of the phrase unspecified. Rather than identifying a particular hoped-for outcome, he aims for a combination of possibility and everyday frustration. He does not plan the illustrations in advance or take requests for the series. Enjoying the drawing process is an important part of deciding what to make next.

For Chicago readers, his visual style may already be familiar. Jones spent a decade illustrating labels for Half Acre Beer Co. and has designed screen-printed posters for bands and other brands. Originally from Fort Collins, Colorado, he has lived in Chicago for nearly three decades, and local landmarks appear elsewhere in his work.

Those Chicago connections include his fantastical hot dog creatures, which draw inspiration from the Superdawg figures in Norwood Park. Another popular print shows pigeons perched above the sign at the Belmont station serving the Red, Brown and Purple lines. These subjects connect his broader illustration practice to places residents encounter around the city.

Jones says the work is made without artificial intelligence. He draws most of the images by hand in Procreate on an iPad, with occasional manually created photo manipulations. He also identifies source material in post replies and alternative text, allowing followers to explore the artistic references behind his changing styles.