Need good advice? Chances are, you’re only a heartbeat away from getting it, according to Catherine Edelman, if only you’d give yourself the permission to ask. “I tell my staff all the time: People love to help,” says Edelman, owner of her eponymous contemporary photography gallery in Chicago’s River North district. “The best thing in business is to ask for help, and never be afraid to know what you don’t know.” This, of course, coming from a dealer who radiates self-assurance. In 1987, Edelman pioneered one of only two photography galleries in the Windy City (and the only one devoted exclusively to contemporary work). She has championed edgy practitioners like Nan Goldin and Joel-Peter Witkin. And perhaps most impressively, she has stuck it out through stock market crashes and recessions, including the most recent one. Lately, thanks largely to her ability to listen—to the beat of her own drummer and to the advice of her young staff of two, assistant director Juli Lowe and general manager Trevor Power—Edelman has also built up an active Web site, edelmangallery.com, that she credits with driving “99.5 percent” of her sales. “I love that at this point, the gallery has a life outside of me,” says Edelman, adding, “that took a while to build up.”

Candid, direct, and clocking in at a commanding five-foot one-inch, Edelman made a series of idiosyncratic, and ultimately smart, career decisions that took her from savvy New York kid to Chicago dealer. Born, raised, and educated on Manhattan’s Upper East Side, Edelman came from a family not particularly involved with art. A strong jewelry-making program at summer camp first piqued her interest in metalworking, a subject she later pursued at the Philadelphia College of Art, at least until her junior year, when she switched to photography. Graduate school in photography at the School of the Art Institute of Chicago, came next (in 1985), but a degenerative eye disease Edelman had been diagnosed with in childhood required immediate surgery before graduation. “I realized I probably wasn’t going to make my living as a photographer,” says Edelman, “I had to find other ways to use my education.” Wasting no time, Edelman forged a business plan for opening a gallery, looked for a site to rent, and took the summer after graduation to criss-cross the country, meeting with every curator and dealer who would see her and show her the ropes. “I was 25,” says Edelman, “and people were really very generous. They gave me mailing lists of collectors in their area; they opened doors for me.”

Edelman’s first show was Nan Goldin’s Ballad of Sexual Dependency in 1988; her second,Men on Men, dealt frankly with issues of male sexuality. Openings were packed, and the gallery was a critical success, but by 1992 her economic picture looked pretty grim. Edelman was ready to pack it in and try for museum work until the Los Angeles County Museum of Art’s Robert Sobieszek, a mentor and favored confidant over the years, gave her his honest counsel: Don’t even apply. “He changed my life,” says Edelman. “He told me that I could do more and say more with the autonomy of the gallery than I could in the museum world. I decided to stick it out.” And how. Edelman expanded, taking a ground-floor space in her building, doubling her square footage—not to mention the rent. Business responded by doubling as well, “and then some,” says Edelman. “They tell you that the worst thing you can do in business is fail,” says Edelman, offering some good advice of her own, “but if you’re fearful and don’t try, you’ll never know if you can succeed.”