The family business literature has thus far not devoted much attention to understanding female vantage points in family firms (e.g. Dumas, 1998; Sharma, 2004). Poza and Messer (2001) and Curimbaba (2002) describe the varying roles that women adopt, but without explaining why they adopt such roles. Our research examines the career progression of women leaders in family businesses, specifically how various roles allow them to progressively learn skills and competencies.In an earlier book (Moores and Barrett, 2002) we found that successful family firm CEOs encountered a series of unique paradoxes. Exploring, understanding and perhaps managing these paradoxes took them on a 1earningjoumey to leadership in which they progressively learnt business (Ll), learnt our business (L2, learnt to lead our business (L3), and learnt to let go our business (IA). Because the sample we used for that study did not include many female CEOs, our present study focuses on women in leadership roles in family businesses to better understand their experience. Our objectives extend those of Dumas (1998) who sought to understand the pathway to leadership in family firms that women travel. Based on interviews with an international sample of women prominent in family businesses, our preliminary results indicate that there are indeed some characteristic journeys that women leaders take to leadership of family firms. We have tentatively labeled them as long march, short journey; swimming against the tide; high roads and low roads; and traveling companions. This paper focuses on the long march, short journey cases and what can be learned from them.