This article explores the consequences of discourses of "boundless receptivity to failure" in advanced digital capitalism, as illustrated by the Silicon Valley mantras "fail often" and "safe to fail" on the individual-subject formation. The article highlights issues related to the temporal dimension in grappling with personal experiences of failure-as a transitional moment between past, present and future-by drawing on Hartmut Rosa's theory of the structural modifications of our relationship to time in late modernity, specifically our perception of the "speeding up of life," and its consequences for subjective forms of selfhood. How has the peculiar relationship to temporality at stake in the subject's experience of failure been reshaped by structural modifications of the "materiality of time?" I first argue that the modern-day agenda for fast recovery pathologizes residual emotional attachments associated with the necessary process of "working out a narrative of failure," as explored by sociologist Richard Sennett. This in turn triggers a greater need to "fix" failure through digital technical procedures. Second, I point to a new design model, the "lean principle," as a paragon of structural modifications of the "materiality of time." I show that this new design paradigm, which has been spreading beyond the industrial sector in which it originates to fuel new modes of thinking and subjectivities, strips the experience of failure out from its temporal dimension. Failure can no longer be represented as a temporal rupture between the present and the future. Such a de-temporalized and renewed signification of failure eludes any subjective libidinal engagement in dealing with "unmet expectations" (i.e., failure).