Following his father's death, young Shissler became John Hull's apprentice in a cigar making business. Three years later, he worked for Albright & Bros and Metzger & Wiley, before excepting a position as a mailman where he served four years. In June 1889,[1] Shissler formed his own business on 52nd North Queen Street, a tobacco firm called Simon Shissler and Son.[2]
In 1890 Shissler was elected as a city council representative from the Democratic Party in a majorly Republican state. After the 1892 election, he served on the Special Water Committee and next year represented the Fifth ward of the state of Pennsylvania.[1]
In 1898, the people of Lancaster, Pennsylvania, voted him in as the twentieth mayor of the city for a two-year term. Simon Shissler decided not to pursue re-election, and in spring 1900 joined the school board of the ward following by a service to the City Democratic Committee.