This study examines the intersection of academic pressure and sleep within Taiwanese families, revealing how cultural norms and expectations shape sleep practices. Through interviews and two-week diaries from eleven families, we found that academic demands significantly influence children's sleep patterns, leading to reduced sleep duration and varied sleep schedules. Our research highlights the importance of integrating care and attuning into the design of sleep-tracking technologies, advocating for a family informatics approach that considers both health needs and social expectations. By exploring these dynamics, we contribute to a broader understanding of family contexts in diverse cultural settings and offer insights for more inclusive technology design.