After earning a degree in business from Pacific Lutheran University in Seattle, Washington in 1990, he attended the graduate program at the Art Center College of Design in Pasadena, California where he earned an M.F.A. in 1997, studying under the artists Mike Kelley, Stephen Prina, Mayo Thompson, Dagmar Demming, and occasionally the visiting John Baldessari.
His first solo exhibition, The Doors at the School of Visual Concepts Gallery in Seattle in 1992, included his pseudo-scientific series, Odaleschatological Essays. Rip-sawn sections of doors were stained, painted, rubbed, scratched and gouged.
Moving to Florence, Italy in 1992, he researched and wrote about the transformation of the socio-political role of early-Renaissance artists. The resulting 1994 book and exhibition Disegni: Via Gino Capponi, 23 featured 80 drawings from over 500 he executed while living in Italy.
Returning to Los Angeles in 1994, Flahiff concentrated on film and video work including the short films Black Hat/Brown Hat which premiered at the Los Angeles Times Media Center, Art Center College of Design in 1997, and Shoebox which premiered at the International Experimental Cinema Exposition in 2000, and the experimental video project Sublimation, first shown at the Royal Melbourne Institute of Technology in Melbourne, Australia in 1996.
Flahiff's awards include the Graduate Merit Scholarship from the Art Center College of Design ('95-'97), an International Studies Scholarship from the School of Visual Concepts ('93), an Emerging Voices Grant from the Puget Sound Group of Northwest Painters ('92), and an Anna K. Merideth Award for International Studies from the Studio Art Center International ('92.)
His work has also been included in several group exhibitions such as Free Press at Röda Sten, (Göteborg), (Sweden), (2006), Transmission/Reception at The Pilot Space, Auckland, New Zealand (1997), Territorial Motif at the Royal Melbourne Institute of Technology, Melbourne, Australia, (1997), and the Pacific Northwest Annual Exhibition at the Bellevue Art Museum, Bellevue, Washington (1992.)