While research indicates that an increasing number of males are experiencing a sense of disaffiliation with traditional education (Kleinfeld, 2006; Steinkuehler & King, 2009), nearly all teenage boys and young adult men (approximately 99%) regularly engage in playing video games of some sort (Roberts, Foehr & Rideout (2008). This is an interesting development because research concerning the affordances of gaming and digital technologies provides increasing evidence that these technologies may sponsor the development of key literacies. The objective of the studies contained in this thesis revolves around exploring the potential affordances of playing massively multiplayer online role playing games (MMOs) as a route toward preparation for future workplace learning (Bransford & Schwartz, 2001). A career and technical education (CTE) framework (Hyslop-Margison, 2005) provided an opportunity to look beyond isolated skills and instead focus on broader, situated (Gee, 2004) vocational practices. I argue that this conceptualization places digital media experiences as more of a sponsor that may provide a bridge to vocational skills development and career exploration by exposing participants to discourse communities (Gee, 1999) that bear strong similarities to the types of skills and dispositions (Thomas & Brown, 2009) required for success in the 21st century workplace. Findings suggest MMO gaming as a potentially productive route toward the practice of 21st century workplace skills, and particularly 21st century literacy practices. Additional findings suggest the importance of informal gaming as an embodied experience constituting an array of identity development opportunities. It is this area--the area of identity--where there appears to be the strongest potential for leveraging friendship-based, interest driven engagement, such as game-based activities, as a step toward helping students develop an understanding of their unique talents and abilities. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]