"It'll take ages"
The item on the side has a size in your head, and the size is why it's still there. The insurance is an afternoon. The form is a saga. The dentist involves being on hold.
Michael Roy and Nicholas Christenfeld, in 2008, had people do tasks lasting between one and fifteen minutes and asked them, before and after, how long the tasks would take or had taken. For tasks under about two minutes, people overestimated, in both memory and prediction. For longer tasks, they underestimated. The pattern is an old one in the study of time, and they'd extended it to exactly the kind of tasks the heap is made of. A two-minute phone call is remembered as longer than it was and predicted to be longer than it will be. That's the felt size, and it's a systematic error, not a personal one.
The same researchers, with Scott Mitten, in another 2008 paper, found that the fix is feedback. When people were told how long the task had actually taken last time, or how long it took others, their predictions improved. Not their effort or their attitude. Their information. That's the chapter 1 exercise, and it's why I asked you to write down the guess and the actual time next to each other. The gap between them is the felt size minus the actual size, and seeing it once changes how the next item looks.
Now, the honest half. The underestimate for longer tasks is real too, and the heap sometimes has a longer task in it. The tax return, the insurance claim with the photographs, the passport renewal. Those take longer than you think, and chapter 24 is about them. What they aren't is most of the heap. Most of the heap is the reply, the signature, the click, the two-minute call, and those are the ones you're overestimating, and the ones that stay on the side for three weeks because they feel like an afternoon.
There's a second thing inflating the felt size, and chapter 19 is about it. An item that's been on the side for three weeks has three weeks of not-doing attached to it, and the not-doing has a weight of its own, and the weight gets added to the estimate. The form isn't a saga. The form plus the guilt plus the fourth reminder plus the fact that you now have to explain the delay is a saga, and only the form is required.
Time one item a day for a week. Write the guess and the actual. By the end of the week the felt size will have started to correct itself, because you'll have information where you had dread.