In this article, I focus on the analysis of some problems in Martin Seligman’s positive psychology based on his two major works. For this, I summarize Authentic Happiness in section two and Flourish in section three. In Authentic Happiness, Seligman, based on three pillars, positive emotion, trait, and institution, suggests six virtues and twenty-four strengths meeting criteria of generality, inherent values, and invariability out of various virtues increasing life satisfaction. He holds that the shortcut to happiness is to develop signature strength fitting for himself or herself. In Flourish, he revises his own theory and suggests a pluralistic concept, wellbeing, instead of happiness for topic, PERMA instead of life satisfaction for measures. He also suggests increase flourishing by increasing positive emotion, engagement, meaning, positive relationships, and accomplishment as goal. In section four, I criticize some problems in his concept of happiness on which we cannot construct any proper systems of virtue theory. His virtue theory entails naturalistic fallacy, instrumental professionalism instead of prudence, arbitrariness and bias in PERMA and virtue lists and disregard for social context. In section five, I analyze unrealistic and dichotomous structure of positive psychology in the matter of happiness. I criticize his ambivalent attitude between reality and virtuality, unjustifiable reduction and black and white in his dichotomous structure of positivity and negativity, arbitrary interpretation on results and paradox of hedonism. I expect that this article would serve philosophical criticism against positive psychology which collaborates with neoliberalism as self-help.