This study investigates how the self-employed define themselves and their businesses in relation to taxation issues, and whether there is evidence that this segment engages with taxation in ways that are different from other segments of the population. Data are collected from a random sample of 2040 Australians. Four domains are chosen for comparison: perceived deterrence for non-compliance, tax morale, perceived fairness, and work practice. As evident in the discriminant function analysis, the self-employed are distinguished by not receiving an annual tax refund, perceiving themselves as paying less than their fair share of tax, having less tax competence and independence, perceiving greater power in the tax office to elicit compliance, favouring small government and minimum government interference, and opposing tax expenditure for redistributive programmes such as health, welfare and education. Findings are discussed in a regulatory context.