By manually bumping a certain task every day, he feels that it is incomplete. He is faced with the reality and forced to either complete the task, delegate it, or bump it again.

(from How Analog Rituals Can Amp Your Productivity discussing why Bob Greenberg, the CEO of the digital agency R/GA writes his tasks every morning despite having access to technical solutions, or probably even a PA to perform this task for him)

When I used to work at Glass's I used a diary to manage my tasks and there definitely is something to be said for the willingness to procrastinate or delay on a task when you know you're going to have to write them out by hand day after day, something which is also covered in the article
Yes, monotony and routine can be truly wearisome. They transform our colorful, over-stimulated existence into black and white. But a task left undone SHOULD be a burden. If you make your system for productivity too productive, you will become anesthetized to your responsibilities.
The 99 percent has been one of most beneficial reads this year. I frequently find something of interest and value in the posts