Most of his life was spent in Missouri, growing up in Lamar and the general Barton County area where he was "Principal of Public Schools" for one term (seemingly at the young age of only 19 or 20), then marrying Katherine Faust in 1873 and moving to neighboring Cedar County, where he became editor (and printer) of the “Stockton Journal” from 1873 to 1878. He continued to study the subject while producing the newspaper and while Superintendent of Stockton Schools for two years. Finally, after studying under Judge Doctorate. P. Stratton, he was admitted to the Stockton bar in 1880, becoming a lawyer
After a few years, he entered politics, running as a Democrat for the office of representative to the state legislature from Barton County, to which he was elected in 1887.
He served in the thirty-fourth Missouri General Assembly, and was on the Judicial Committee. Several years after his career as a legislator ended he was elected Judge of the Twenty-sixth Judicial Circuit Court, a position he held for about five years.
After that time he was usually called Judge Timmonds. During his years as a judge, Henry Carroll Timmonds tried one case which involved much local and even some national interest, one of the so-called "boodle" trials.
These cases involved several state senators who had solicited "boodle" (bribe money) in exchange for their votes.
Oddly, this was not contrary to any Missouri statute at the time. Judge Timmonds, though, found Senator West. P. Sullivan guilty under the common law, and the senator was convicted and fined, thus setting a significant precedent. He died on July 4, 1913.