The focus of this essay is Moritz Schlick’s On the Meaning of Life. Schlick wrote On the Meaning of Life in 1927 and hoped to push back against pessimist currents of thought that were popular at the time by using the concepts of play and youth. Schlick defines plays as any “activities which carry their own purpose and value within them, independently of any extraneous goals…” (Schlick, M. 2008, p.64). For Schlick, these intrinsically valuable activities are the key to creating meaningful lives. However, I argue that there are certain tensions in Schlick’s essay that need addressing. In the first half of this essay, I make some vital changes to Schlick’s theory of play in order to address these tensions. In particular, through a discussion of Aristotle’s concepts of leisure and play, along with Mihaly Csikszentmihalyi’s concept of flow, I argue that play should be understood as a state rather than as certain activities. I also explore aspects of Schlick’s writing such as his distinction between joy and pleasure and the potential criticisms that could be levelled at this distinction. By addressing the tensions in Schlick’s work and by clarifying his theory of play, I hope to show that play is a serious candidate for giving us more meaningful and fulfilling experiences. Having addressed the issues in On The Meaning of Life, the second half of this essay is dedicated to showing how we can maximise play in our lives. To do this, I begin with an exploration of the relationship between our values and play via a discussion of Friedrich Nietzsche’s writing and argue that in order to maximise playfulness in our lives, there is a subsidiary task, which is to uncover and analyse our own values. Lastly, I argue that playfulness is a skill that we can, and ought, to develop, and explore Csikszentmihalyi’s suggestions for how we might develop this skill