Distinctive styles of client decision-making have emerged from case study research into the effectiveness of career guidance. This paper explores some findings from the third year of a longitudinal study currently underway in England, which relate to the ways clients approach transition points in their careers and make the decisions that move them on. Data analysis reveals four career decision-making styles: evaluative, strategic, aspirational and opportunistic. Overall, it is evident that the choices and decisions made as individuals progress towards longer-term career destinations are multi-dimensional, complex, sometimes being implemented over an extended time frame and not always rational. For practice, implications of these findings include the need for practitioners to place less emphasis on planning for certainty and more tolerance of undecidedness. The first three years of the longitudinal case study into the effectiveness of guidance have, unsurprisingly, seen most participants engage with a range of career transitions. These have included: gaining higher education qualifications; returning to education; upskilling or reskilling in their jobs; changing jobs and/or occupational sectors; and volunteering. Others have remained under-employed or unemployed. Often in parallel with career transitions, research participants have been coping with important life events like: re-locating, sometimes abroad; getting married; getting divorced; giving birth; coping with ill-health; adjusting to childcare responsibilities; and dealing with elder care. Personal reflections on these career transitions and life events, recorded in interviews conducted as part of the research, provide insights into the ways these individuals make choices and decisions. The fourth and fifth phases of data collection (2006 to 2008) will allow scrutiny of the extent to which these styles might change over time (Gati & Saka, 2001).