This chapter examines Harriet Martineau’s approach to gender politics through her understanding of ‘manliness’ as explored in a selection of her Illustrations of Political Economy (1832−4). It was a concept essential to her configuration of male leadership fit for the testing times of the early 1830s, and highly topical. Published when the pressures experienced by men of all classes were being highlighted in periodicals and novels, the tales address the differences between ‘personality’ and ‘character’ in crises faced by fathers and husbands, magistrates and petty criminals, trades union activists, landowners, and slave-owners, at home and in the colonies, as they debate the injustices of their living and working conditions. This chapter argues that Martineau’s interventions in contemporary debates about masculinity shift the focus to a new kind of conscientious working man whose values are tested in cross-class dialogues in public places. It explores the ways in which the Illustrations show how men collaborate and compete within their communities, and the ambiguous gender messages arising from patterns of reward and punishment that seem to devalue otherwise positive characteristics.