Present day ideals of good parenting are socio-technical constructs formed at the intersection of medical best practices, cultural norms, and technical innovation. These ideals take shape in relation to the fundamental uncertainty that parents/mothers face, an uncertainty that comes from not knowing how to do what is best for one's children, families, and selves. The growing body of parent-focused smart devices and data-tracking platforms emerging from this intersection frame the responsible parent as one who evaluates, analyzes, and mitigates data-defined risks for their children and family. As these devices and platforms proliferate, whether from respected medical institutions or commercial interests, they place new demands on families and add an implicit emphasis on how humans (often mothers) can be augmented and improved by data-rich technology. This is expressed both in the actions they support (e.g., breastfeeding, monitoring food intake), as well as in the emotions they render marginal (e.g., rage, struggle, loss, and regret). In this article, we turn away from optimization and self-improvement narratives to attend to our own felt experiences as mothers and designers. Through an embodied practice of creating Design Memoirs, we speak directly to the HCI community from our position as both users and subjects of optimized parenting tools. Our goal in this work is to bring nuance to a domain that is often rendered in simplistic terms or frames mothers as figures who could endlessly do more for the sake of their families. Our Design Memoirs emphasize the conflicting and often negative emotions we experienced while navigating these tools and medical systems. They depict our feelings of being at once powerful and powerless, expressing rage and love simultaneously, and struggling between expressing pride and humility. The Design Memoirs serve us in advocating that designers should use caution when considering a problem/solution focus to the experiences of parents. We conclude by reflecting on how our shared practice of making memoirs, as well as other approaches within feminist and queer theory, suggest strategies that trouble these optimization and improvement narratives. Overall, we present a case for designing for mothers who feel like they are just making do or falling short, in order to provide relief from the anxiety of constantly seeking improvement.