The focus of this paper is the transition of managers and professionals out of organisational employment into portfolio work. The interest in this individual transition is its resonance with wider debates about the changing nature of career. The demise of the traditional hierarchical career is widely predicted as is its replacement by a proliferation of more fluid and individual career choices, encompassed in the over-arching notion of the boundaryless career. The two studies on which this paper is based have taken an in-depth look at individuals who appear to exemplify this move out of organisational employment and into more independent working. The paper draws inductively on interviews with individuals who had left organisations to set up on their own. Hence the data is grounded in the accounts of individuals and seeks to explore their interpretations of their experiences. The paper focuses on participants' expectations of their new employment context and its realities. In considering the major implications of these findings, it questions dualistic conceptualisations of career and argues for theoretical frameworks based more on synthesis and linkage.