Interactive technologies provide today's youth a low stakes sandbox to collect experiences (Gee, 2004) and try tasks and identities (Gee, 1991) that push the boundaries of "known" and open up the world of possibility. Pairing affordances of video games with the possible selves framework (Markus & Nurius, 1986), research involved using The Sims 2 life-simulation properties to encourage a friendship group of teenage males to create simulations of their hoped for and feared potential selves. While all participants reported increased crystallization (Super, 1981) of characteristics within their hoped for future self, at the conclusion of the intervention most participants still demonstrated an imbalance between feared and hoped potential selves. This suggests the need for additional work in the area of vocational and academic asset exploration, as well as the need to connect the consideration of possible self actualization to believable and realizable action plans.