Over the past two decades the economies of Canada and many other industrialized countries have seen significant restructuring, bringing with it steadily rising levels of self-employment and small business ownership. Women have been at the forefront of this change. Of the many questions raised by women’s entrance into self-employment, a central one concerns the factors fuelling its growth. While some argue that women have been pulled into self-employment by the promise of independence, flexibility and the opportunity to escape barriers in paid employment, others argue that women have been pushed into it as restructuring and downsizing has eroded the availability of once secure jobs in the public and private sector. To date, existing research on the ‘push–pull’debate has not fully answered; these questions, with survey and labour force data suggesting only general and sometimes contradictory, trends. This article examines this issue in greater detail, drawing on in-depth interviews with 61 self-employed women in Canada. Overall their experiences shed further light on the expansion of women’s self-employment in the 1990s, suggesting push factors have been underestimated and challenging the current contours of the ‘push–pull’ debate. Participants will earn 1 Learning CEU after reading the article and completing the 10-question quiz to 100%.