In The Guild, the player may follow whichever career path they choose. These range from Blacksmith to Innkeeper, going through Thief and Money Lender as well as a few others. As the character ages and gets richer, the option to acquire new professions will emerge. In this way, the fourth generation of the player's dynasty might have access to more than four professions, while the first one will have only one. Each profession within a family has its own business establishment.

To run a certain business, it's necessary to possess the respective title given by an "association" (a guild of sorts). Titles enable the player to have an establishment but it also determines what type it will be. Titles also come with levels and the higher the player goes on the ladder, the better the businesses available become. The player may only apply for the next level (or first, in case they're not specialized in that job) of the profession when a given criteria is met.