Modern societies are growing richer, but are we becoming happier and wiser? The current rarity of wisdom and its elitism runs parallel with the illusion of the pursuit of happiness and wisdom normalizing self-empowering, agentic life styles rather than communion-oriented, prosocial attitudes and behaviors. Moreover, little is known how diversely people understand wisdom and wisest persons that they know in person for what reasons, which inquire what it really takes for laypeople to be wise across their life course and whether there is an association between different life paths and circumstances with diverging wisdom developmental trajectories. As part of a multinational wisdom project, this study investigated how and to what extent wisdom characteristics are understood differently between the top-10 and bottom-10 wisdom-score groups in terms of their wisdom nominees in person and their own version of wisdom definition. A mixed-method analysis adopted a social network analysis and nonparametric statistical method for a quantitative configuration and content analysis for a qualitative specification. The nonparametric t-test indicated that the top-10 wisdom-score group valued warmth and prosocial behaviors significantly higher than the bottom-10 group. They also had higher life satisfaction and better health status than the bottom group. The social network analysis visualized the relations among wisdom characteristics and compared central characteristics between the top-10 and bottom-10 group. The bottom group identified more individuality-oriented, self-centered personality development attributes as wisdom characteristics, whereas people in the top 10 seemed to appreciate the virtue of perspective taking and learning from experiences and others, indicating the importance of altruistic, reciprocal attributes as prerequisites for wisdom development.