The increasingly unpredictable, individualized and short-term nature of the labour market is evident in the careers of advertising creatives. We explore the career trajectories of 48 creative professionals in the British advertising industry, using theories of situated learning and communities of practice to illustrate how the collective remains important to individuals' career prospects. Creatives learn their craft by becoming immersed in the multiple, inter-related communities that constitute the advertising world during the demanding 'pre-peripheral' and 'peripheral' stages of their career. Learning through immersion continues throughout the journey from the periphery to the centre, since creatives participate in a competitive, tight-knit creative community, actively engaged in social networking and constantly monitoring each others' creative output. Creatives' legitimacy (and power) is earned by winning peer regard for their work. The nature of the learning required changes as each stage of the creative trajectory brings different motivations and pressures, but the processes of learning, the mutual shaping of individual and community, and the identity work involved are evident throughout creative career trajectories.