The speaker explains that while automating tasks in a to-do list seems efficient, it often leads to overwhelm because life is unpredictable and not everything can be automated. Unexpected events can disrupt planned tasks, making automated lists impractical. To combat this, the speaker suggests a five-minute daily planning session to review tasks and calendar events, ensuring that the day's tasks are manageable. This involves prioritizing tasks using a system like Todoist, where tasks are categorized by priority levels (P1 to P4). The speaker emphasizes the importance of rescheduling tasks without guilt, as life is inherently unpredictable. They recommend not automatically rescheduling incomplete tasks for the next day to avoid backlog, and instead, realistically assessing when tasks can be completed. The speaker also highlights the importance of a weekly planning session to keep projects on track and reduce stress.