In the civic realm, Kiplinger is active in nonprofit governance and philanthropy, especially in the fields of secondary education, choral music, and historic preservation.
As a public speaker, Kiplinger frequently addresses audiences of corporate and civic leaders, on such topics as the economic outlook, politics, investing and ethical business management.
He enrolled in the seventh grade at Landon School, a private boys’ school in Bethesda, Maryland, when his parents restored and moved to "Montevideo," an historic farm in Seneca, Maryland, 20 miles northwest of Washington, D.C. As a boy he played piano and folk guitar, swam on a community team, competed in equestrian events with the Seneca Valley Pony Club and foxhunted with the Potomac Hunt.
He was a member of the Alpha Delta Phi fraternity and was elected president of Quill and Dagger, a senior men's honorary society for student leaders.
[2] During the summer of 1968 he was an aide and writer in the U.S. House campaign of Democratic candidate John S. Dyson, a Cornell friend (class of ‘65) who narrowly lost to Republican Hamilton Fish in the general election for the congressional seat in the mid-Hudson region of New York State.
[3] After graduating from Cornell, Kiplinger enrolled in the two-year master's degree program at Princeton University's Woodrow Wilson School of Public and International Affairs, majoring in economic development studies.
Kiplinger started his professional reporting career in 1970, with a brief stint at the Montgomery County Sentinel, an award-winning weekly in Rockville, Maryland, under editor Roger Brooke Farquhar.
[5] Kiplinger was a Washington correspondent (1970–73) and bureau manager (1976–78) at the Griffin-Larrabee News Bureau, which provided daily Washington coverage to more than 20 newspapers throughout the country, from Maine to Alaska, including all the community dailies of the Ottaway Newspapers subsidiary of Dow Jones & Co. One of Kiplinger's stories revealed that a Pocono Mountains (Pa.) vacation home development, whose deceptive sales practices had been cited by the federal government, was owned by a U.S. senator who sat on the committee that oversaw the regulation of interstate land sales; the senator soon sold the project.
[6] For six years (1978–1983) Kiplinger was chief of Ottaway News Service, overseeing coverage from the chain's bureaus in Washington, Albany, Boston, and Harrisburg.
“I spent the first 13 years of my journalism career in the employ of others, as a Washington correspondent and bureau chief, making my mistakes on their dime, learning reporting, editing and management before coming to Kiplinger,” he said in a 2001 interview.
“So our strategy is to ‘monetize’ the non-paying reader, by providing a certain amount of free content to attract them to our ad-supported Web site” and then introduce them to our subscription services.
As members of this large chorus, Kiplinger and his wife have sung in dozens of Kennedy Center performances with the National Symphony Orchestra, under such renowned conductors as Mstislav Rostropovich, Leonard Slatkin, Seiji Ozawa, Sarah Caldwell, and Karl Richter.
It supports a wide array of charities in the Washington area and nationally, in the fields of secondary and higher education, professional development for journalists, the arts, social service and historic preservation.