With increasing evidence highlighting the link between psychological factors such as self-esteem, self-efficacy and optimism on employability outcomes, this paper reports an evaluation of a unique student experience initiative called 'Life Design' developed to support the professional and personal development of undergraduate students. First year undergraduates engaged in a two-hour workshop involving interactive exercises designed to foster self-reflection, self-efficacy, and career optimism. The impact of this workshop on validated self-report measures of self-esteem, self-efficacy, and optimism, alongside career-related outcomes was explored using a prospective longitudinal design. Analyses revealed a significant immediate and sustained increase in self-esteem following Life Design, but no impact on self-efficacy or career optimism. Certainty of career developing steps increased at a later follow up, but no changes to career prospect confidence or career choice certainty were reported. This paper highlights the benefits and wider challenges of delivering and engaging students in initiatives designed to enhance employability.