Instead of running for re-election to the state House of Representatives in 1976, Densmore decide to run for the
Oregon Secretary of State position. In 1978, Densmore left his teaching job and started a new career as an
insurance agent. While he continued to sell insurance, he also became a chartered life underwriter in 1983 and a chartered financial consultant in 1985. Densmore was later elected president of the Rogue Association of Insurance and Financial Advisors. During this time, Densmore was also elected chairman of the board for the
Southern Oregon Education Service District. He stayed on that board for the next 16 years. In 1989, Densmore left the Democratic Party and registered as a
Republican. Densmore's decision to change parties was the result of his belief that the Republican Party was more responsive to the needs of small-business and better prepared to manage the overall economy. Seven years later, he attempted to win another term in the state legislature, representing District 50. This time, he ran as a Republican. However, he lost the 1996 primary to the Republican incumbent,
John Watt. In 2006, Densmore decided to run for a seat on the Medford city council. He was elected and took his seat in early 2007. He was re-elected in 2010. Densmore remained on the council until he resigned in 2013. During his tenure on the council, Densmore championed a number of city transportation projects. From 2007 to 2010, he also served on the board of directors for the Southern Oregon Regional Economic Development Corporation. In addition, he was a member of the Medford Urban Renewal Agency board, a member of the Bear Creek Valley Rotary Club, and served as president of the
Bear Creek Greenway Foundation. In 2015, after 36 years as an insurance and financial consultant, Densmore took a new job with a Medford area
lobbying firm. He is currently the firm's resident transportation and economic development expert. == Personal life ==