In 2005, I embarked on a two-year, full-time training programme in fine woodwork at the historic Building Crafts College in Stratford, East London. Direct participation in a community of learners and practitioners formed an integral part of a longer anthropological study of skill acquisition, practice and professional identity among contemporary English furniture makers. Based on that fieldwork, this chapter explores the growth, development and deterioration of craft skill over a lifespan from the perspectives offered by three generations of woodworkers. A carpenter’s dedication and skilled know-how may extend well beyond the working life of the individual craftsperson. This chapter begins and ends with George, a ninety year-old woodworker whose memories of apprenticeship and practice draw my starting point back to the 1930s in southeast England, and whose acts of generosity have made training possible for future generations in the trade. The accounts in between from carpenters Jack and James investigate in turn the early woodworking education of a young man and the professional practice of an established, middle-age designer-maker whose initial role as apprentice has, with passing years, turned to mentor. Woodworking presents constant challenge and mastering the craft demands a persistent willingness to learn and develop. A woodworker’s skill is measured by his or her ability to creatively respond, problem solve and incorporate new information into their working processes. Design and making, therefore, are skills that grow in response to, and in relation with, the total working environment of tools, machinery, materials, fellow carpenters and clients. This theme remains central throughout my investigation. Design and making, as interrelated skills, evolve in unforeseen ways, producing unique solutions to problems that gradually come to be associated with individual ‘style’. But skill-based knowledge does not merely grow and develop. Like the organic properties of the timber they work, skill, too, is susceptible to deterioration and decline. The final section of the chapter returns to George in order to explore the impact of aging, injury and illness on tool-wielding practices, and the re-skilling strategies devised by those determined to remain active in their cherished trade. In relation to this, I reference literature from the neurosciences that examines transformation in the nervous system as the body grows, practices and ages. Anthropologists have long challenged Cartesianism and entrenched divisions between ‘exterior person’ and ‘interior self’, and suggest that self and identity are constantly in the making. The neurosciences literature further supports this claim by illustrating how our brain and nervous system, too, are ever-changing. Engagement with such interdisciplinary research deepens our understanding of aging and transformation, and in doing so informs discussions of what is entailed in processes of growth and making. In this chapter, I weave theory and analysis into the ethnography. The woodworkers I trained with and interviewed reflected carefully on their own processes, choices and personal development as craftspeople, and they articulated their thinking on these matters as elegantly as they wielded their tools. I therefore include detailed quotations from their accounts alongside my own explanations, through which I bring narrative order to the events we discussed and the things that I learned from them.