Abstract: Generation Y is recognized as overly self-confident and self-absorbed (Pew Research Center, 2007) and lacking loyalty and work ethic (Marston, 2009). On the other hand, they are characterized as emphasizing the type of work they do rather than their employing organization, trying to work more efficiently and flexibly, and pursuing feedback from superiors for career advancement (Brown, et al., 2009). These unprecedented characteristics of generation Y have provoked scholarly moves toward investigating how to increase its work engagement level. In this study, the protean career attitude (PCA) and work engagement (WE) are employed because of their relatedness to generation Y’s characteristics. The protean career is driven by a person, not an organization, which can represent an individual’s diverse experiences concerning one’s career (Lee, et al., 2016). PCA, composed of self-directedness and value-orientation (Briscoe & Hall, 2006), is positioned as an influential variable on WE, as found in the prior studies (De Vos & Segers, 2013; Herrmann, Hirschi, & Baruch, 2015). WE can be defined as “a positive, fulfilling, work-related state of mine that is characterized as vigor, dedication, and absorption” (Schaufeli, et al., 2002, p. 74), which could be a convincing consequential variable for generation Y who are likely to be immersed in their work. This study mainly focuses on masteristic work (MW), which refers to an individual’s formative originality accumulated through work experiences across the lifetime and is composed of three components – work orientation (WO), proactive work (PO), and work creation (WC) (Koo, et al., 2021). Specifically, WO means that an individual pursues to be delightful and meaningful in their work and integrate their work and life. PO is related to an individual’s sincerity and strong conviction regarding their work. WC reflects whether an individual work with creativity and openness towards innovation. In this study, MW is set as a mediating variable in the relationship between PCA and WE, because generation Y tries to construct their career path according to value and is likely to identify with their work, so MW can be an explainable variable for this generation. The research questions for this study are as followed: First, does MW mediate the effect of PCA on WE? Second, in detail, how does each factor of MW work in this relationship? The subjects of this study were generation Y in South Korea, born between 1979 and 1994 (Smola & Sutton, 2002), and finally, a total of 793 responses were analyzed (the average age was 35.13). In addition, PCA (Protean Career Attitudes) (Briscoe, Hall, & DeMuth, 2006), MWS (Masteristic Work Scale) (Koo, et al., 2021), and a short version of UWES (Utrecht Work Engagement Scale) (Schaufeli, Bakker, & Salanova, 2006) were utilized for the questionnaire, and all were implemented a 7-point Likert-type scale. All measurements secured reliability and validity. As a result of mediation analysis via Process macro model 4, MW mediates the relationship between PCA and WE; in this model, the total effect was .748, the direct effect was .259, and the indirect effect was .490, all of which were statistically significant. In addition, for examination of the indirect effect of each subfactor of MW, multi-mediation analysis was conducted through Process macro model 4. As a result, WO (.368), PO (-.111), and WC (.133) all had a significant indirect effect. For generation Y workers, working with self-directedness and value-orientation leads to a high level of engagement in their work, and this causality is also possible through working masteristically. Specifically, three subfactors – WO, PO, and WC – have a significant partial mediating effect in this causality; but it is noteworthy that the indirect effect of PO was negative although the others show a positive indirect effect. It signifies that if generation Y workers are directed to work voluntarily and by themselves, they would likely treat their work with high levels of vigor, dedication, and absorption, which also is processed through their identification with work and innovation behaviors. However, no matter how young workers with self-directedness and value-orientation to their work are likely to work with agency and strong convictions, the intervention of exogenous variables can disturb the effect of PO on WE, such as the organizational culture (Barbars, 2015), job characteristics (Sulea, et al., 2012), and leadership style (De Clercq, et al., 2014; Ghadi, Fernando, & Caputi, 2013). It means that some situational variables can impede a process in which working proactively leads to work engagement. Further studies for investigating the exogenous factors are needed, which can contribute to developing interventions for encouraging generation Y’s engagement at work.