The chaos theory of careers was applied to identify the connections between multiple jobholders' careers and societal change. Multiple job holding is a form of employment that consists of two or more overlapping jobs. Six interviews with men born in the 1960s in Finnish North Karelia, whose multiple job holding included agricultural and forestry work, were analyzed. Our results showed that multiple job holding career development has societal connections and that the experiences of multiple job holding varied across individuals. Moreover, multiple job holding experiences and further career development endeavors were influenced by whether the multiple job holding career developed in line with or counter to societal changes. The study contributes to the chaos theory of careers by showing that self-similar fractal shapes can be identified both in individual careers and in societal changes by studying connective metaphors.