 Keisling graduated from Sunset High School, then located in an unincorporated area of Washington County, in 1973.He graduated from Yale University in 1977 and pursued a career in journalism, first as a writer for Willamette Week in Portland, Oregon from 1978–1981, and then as an editor at "Washington Monthly" in Washington, D.C. from 1982–1984.From 2000 to 2009, Keisling was a Senior Vice President for Marketing for the Oregon high tech company CorSource Technology Group, Inc. (formerly Hepieric, Inc.), has remained involved in politics and civic affairs since leaving office, serving on a variety of local, statewide and national committees, commissions and organizations, both inside and outside of government.