Big data and predictive analytics applied to economic life is forcing individuals to choose between authenticity and freedom. The fact of the choice cuts philosophy away from the traditional understanding of the two values as entwined. This essay describes why the split is happening, how new conceptions of authenticity and freedom are rising, and the human experience of the dilemma between them. Also, this essay participates in recent philosophical intersections with Shoshana Zuboff’s work on surveillance capitalism, but the investigation connects on the individual, ethical level as opposed to the more prevalent social and political interaction