In a striking passage from the last book of his Tusculan Disputations, Cicero claims to live from day to day (nos in diem vivimus; 5.33). He always opts for what he deems probable, and this, he argues, also constitutes his freedom. This remarkable statement, which is obviously rooted in Cicero’s Academic philosophy, is far from unproblematic. This contribution aims at a better understanding of Cicero’s claim, through an analysis of his argumentative strategies in Tusculan Disputations. More precisely, attention is given to Cicero’s use of (1) the argument from common sense, (2) the argument from dignitas and decorum, (3) illustrative examples, and (4) to his approach in introducing the philosophical topics of the conversation. Finally, I deal with the complicated question as to whether Cicero’s sophisticated attitude of in diem vivere can be reconciled with the therapeutic goal of Tusculan Disputations.