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Entrepreneurship is one of the fields where the concept of career has found application as an analytical tool. However, considerable gaps exist in operationalization and measurement of this concept. Using the qualitative in-depth interview which collected from entrepreneurship training participants, this paper addresses some of these gaps. Meanwhile, the need for this research stemmed from the fact that in today-s new world of young generation, the new world of work, organizations and markets are demanding new skill sets, innovative approaches to delivery and increasingly higher performance levels. The impacts of technology and globalization and the demand for entrepreneurs have brought a new era in economies and organizations, resulting in new career realities. The purpose and direction of the young entrepreneurs- career is no longer confined to a single employer boundary. Therein lies the opportunity for young generation to understand, manage and leverage this dynamic context for entrepreneurship career progression and growth through the accumulation and implementation of relevant and valued career capital. This research investigated the three components of entrepreneurial careers for the young generation, particularly in Bandung City, Indonesia. This research examine how entrepreneurial careers are shaped by three components, namely motivations (knowing-why), knowledge (knowing-how), and relationships (knowing-whom). The findings of this research could provide an insightful platform for further research by exploring the presence of those three components in another city around Indonesia.