Given the importance of experiencing fulfilling and productive workdays, scholars have focused on ways to boost employees’ daily engagement and performance, suggesting this may be accomplished by increasing meaningfulness of their work tasks. However, an alternative approach may be needed in multifaceted work contexts where employees need to complete sets of varied tasks each day, including tasks that lack meaningfulness. To address this issue, we integrate the workday design perspective with research on residual engagement to examine implications of strategically sequencing tasks in terms of their meaningfulness. We theorize that because of a process we refer to as engagement cascade, performing the day’s most highly meaningful tasks earlier and in a concentrated manner will tend to produce higher levels of daily engagement relative to sequences in which the most highly meaningful tasks occur later or are disbursed. We use agent-based modeling to formalize the engagement cascade process and generate specific predictions regarding how daily engagement is impacted by different task meaningfulness sequences. Findings from an intensive longitudinal design study with NASA and ROSCOSMOS crew members (Study 1), an experience sampling field experiment with full-time employees (Study 2), and two controlled laboratory experiments with undergraduates (Study 3 and Supplement to Study 3) provide support for our hypotheses. Specifically, the decreasing task meaningfulness sequence engendered higher levels of daily engagement, and in turn, daily performance, relative to increasing, inverted U-shaped, and U-shaped sequences.