While in grad school / law school, he also studied law with James Rood Doolittle.[2] He then joined Doolittle's law firm, with the firm becoming Doolittle, McKay & Tolman in 1889 (and later becoming Doolittle, Palmer & Tolman).[2]
From 1901 to 1902, he was attorney for Chicago's Board of Local Improvement.[2] He was then corporation counsel for the City of Chicago from June 12, 1903 until August 1, 1905.[2]
After leaving government service, he was the senior member of his own law firm, Tolman, Redfield & Sexon.[2] He served as president of the Illinois State Bar Association for 1917-18.[3]
Tolman married twice, to Nellie May Brown and Blanch Stevens. He died at the age of 88 on November 20, 1947, in Chicago, where he is interred at the Oak Woods Cemetery.