This article reports on the effect of life-design counselling on a purposefully selected learner from an environment challenged by disadvantages. An instrumental, single-case study approach was followed and collection and analysis of quantitative and qualitative data proceeded simultaneously. Intervention comprised assessment and dialogues and investigated the influence of life design counselling on the contextual experiences of the participant. We focused on the four dimensions of career adaptability and on the meaning of career in the future life of the participant. The intervention enabled the participant to pursue a dream, to set goals, and to (re-)establish his career-life identity; rekindled his hope; and enhanced his self-efficacy. After the intervention, he felt more positive, less anxious, and more ready to look at the positive side of his life. Longitudinal research and quantitative studies are needed to confirm the value of the intervention described here.