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Drawing from Higgins’s (2012) regulatory focus theory and the conceptualizations of positive and possible masculinities (Davies, Shen-Miller, & Isacco, 2010; Kiselica & Englar-Carlson, 2010; McDermott et al., 2019), this study sought to better understand how men conceptualize variations of their personal manhood and if they see barriers between these masculinities and their present selves. Young adult men in university (N = 44) were randomly assigned to 1 of 2 conditions that prompted them to reflect on their masculinity from either an “ideal” or “ought” framework and to report perceived barriers, if any, to demonstrating that masculinity. For each question, participants could generate up to 5 responses for a possible total of 220 cases. Consensual qualitative research—modified (Spangler, Liu, & Hill, 2012) was used to explore their responses. Physicality, wellness, self-reliance, relational, knowledge, prestige, player, career-oriented, confidence, logical, and citizenship emerged as categories. Several categories were reported too infrequently to be included in further analyses (e.g., physicality). Men’s response frequency differed significantly between groups, suggesting that men’s conceptualizations of their “ideal” and “ought” masculinities are distinctly characterized, χ2(6, N = 194) = 16.27, p = .01. Although identified barriers were also significantly different, χ2(4, N = 199) = 20.92, p < .001, similar identification of negative self-evaluation (37%) for both conditions presents compelling concerns regarding men’s perceptions of their ability to demonstrate gender norms even within new frameworks. Implications and future directions are discussed with a focus on highlighting challenges to current theory and informing future theorists and researchers.