“Time Waits for No One,” reads the mammoth orange needlepoint sign by artist Amanda Ross-Ho on the wall of Carrie Secrist Gallery’s 20th anniversary exhibition. It could serve as a slogan for Secrist’s past, present, and future.

After two successful decades representing artists with her Chicago-based gallery, Secrist isn’t dawdling on the past. As her signature windswept hairstyle suggests, the 44-year-old gallery owner is always looking ahead.

Secrist started as a gallerist—a term she prefers over dealer—by taking lead of Gallery A in the River North gallery district in 1992. By 2003 she relocated to the younger West Loop district and finally put her own name on the door. “You have to do it,” she says of the eponymous nomenclature. Branding confidence, it seems, is required to get artists, collectors, and critics behind one’s vision.

Over the last 20 years, Secrist has seen many changes in the art world. The internet has totally altered the landscape, she says, because the gallery gets less foot traffic if armchair website surfers feel they’ve already viewed a show from their bedrooms.

The biggest change, however, has been the proliferation of art fairs. Back in the day, Chicago’s original fair on Navy Pier, and the original Basel fair “felt like the Oscars,” says Secrist. Nowadays, the fairs are like a plague, she says, with one opening nearly every two weeks. But that also increases gallery sales. Secrist estimates she makes 90 percent of her sales at the art fairs. (And yet, having a physical gallery space is a requirement to participate in the top fairs.) 

The career of a gallerist in the relatively small Chicago market has never been guaranteed, and Secrist has survived many obstacles. For example, the gallery’s thematic exhibition about the pure delight of humorous art bombed when it opened the day after September 11. But Secrist kept the show open and viewers finally came around, even finding reprieve in the theme. Another hit came in 2008, following the economic recession. Secrist wondered if anyone would buy art ever again. (Spoiler alert: They have and they will.)

But these hurdles haven’t curbed Secrist. Rather, now with the help of Stevie Greco (formerly of Donald Young Gallery), whom Secrist hired as director in 2011, the gallery is drastically changing gears. Secrist and Greco are shaking up their stable of artists and picking up new talent to support, such as Andrew Holmquist and Derek Chan. It’s the only way Secrist Gallery can stay fresh, relevant, and alive for another 20 years.

Secrist is now heavily invested in refreshing her gallery’s identity. When picking up new artists to represent, she says she must be personally inspired by the work. And to emerging gallerists, she offers a piece of advice: Choose your own heroes.

Photograph: Courtesy of Carrie Secrist