Using a within-individual perspective, we examine (a) in what ways an individual’s entrepreneurial aspirations are either enhanced or eroded by professional and leader/managerial career aspirations; (b) how personality traits and values explain entrepreneurial career intentions in relation to motivation and efficacy; and (c) how primarily entrepreneurially-motivated students are more boundaryless in their career mindset than professionally- or leadership-motivated students. We propose a three-dimensional “career space”, which builds on Kanter’s (1989) proposal of three principal career forms in society – bureaucratic (or leader/managerial), professional, and entrepreneurial careers – as a framework to illuminate connections among careers beyond extant individual-psychological or organizational perspectives.