In 1874, Bliss moved to Chester, Pennsylvania. He worked as a teacher while studying law and was admitted to the Delaware County bar in 1878.[4]
In 1881, Bliss began publishing a weekly legal journal, of which 5 volumes were published in book form under the title "The Delaware County Reports". He also published a "Digest of the Local Laws of Delaware County".[5]
In 1882, Bliss became owner and editor of the Delaware County Republican newspaper in Chester, Pennsylvania and continued in that capacity until 1893.[6] He was an incorporator of the Cumberland Telephone Company, later renamed the United Telephone Company. He worked as general counsel for the United Telephone Company.[4] He had a law partnership with A. B. Geary.[7]
He worked as chair of the Delaware County Republican Committee in 1887 and was elected to the Pennsylvania House of Representatives for Delaware County defeating Albert Magnin in 1889. Bliss was re-elected to serve eight consecutive terms, served as chairman of the committee of appropriations[4][8] and as Majority Leader from 1903-1904.[1]