This paper explores the ways in which financial speculation and disruption have become common traits defining our artistic and political imagination. In this discussion a variety of notions emerge – namely, the move from value to price, from labor to debt, from revolution to disruption, and from avant garde to speculation. Finance is speculation on debt. Speculation is commonly used in recent years in philosophy, literature, politics, the arts and the sciences. As varied as the usages of the term may be, the current emergence of speculation in these different fields stems from the world of finance capital and its premise of managing risk. Speculation proves to be a form of pragmatism that generates more and more extreme models within the current system of control and accumulation by dispossession. Whatever the extreme scenarios it generates might be, they always depend on a stable variant – the continuation of finance capital. This paper wishes to offer in addition, the notion of counter-speculation by using the work of contemporary thinkers and artists. Counter-speculation invites potentials for actualization. While exploring new forms for being in uncertainties against financialization, counter-speculation assigns scenarios and narration that actualize onto the present its own potentials. By that it opens a new horizon for our political imagination beyond finance.