[1] He was educated in public and parochial schools of Kenosha and worked for most his young adulthood in a retail grocery business owned by his father.

His company would soon expand into real estate, and he would end up running the company—known as Charles H. Pfennig, Inc.—for the rest of his life.

[8] In 1906, however, Pfennig ran for office again, and was narrowly elected to a two-year term as Sheriff of Kenosha County.

He challenged incumbent state representative Mathias J. Scholey, who had also recently served as Mayor of Kenosha.

The income tax was supported by Republican Governor Francis E. McGovern, but was vehemently opposed by both Pfennig and his Democratic opponent.

[13] True to the polls, Pfennig prevailed in the November general election taking 54% of the county vote.

[17] In addition to his insurance and real estate business, Pfennig was invested in the Terrace Court Corporation, was a director of the Brown National Bank, and was president of the Greenridge Cemetery Association.

He was also a member of the Kenosha Salvation Army, the Benevolent and Protective Order of Elks, Modern Woodmen of America, and Rotary International.