Is Your To-Do List Realistic, or Wishful Thinking?

Are you a list-maker?  I'm an avid list-maker, but not really such a great list-follower.  Every evening I get my to-do list set up for the next day, and during the day, one of the first things I do is to review my list and make last-minute changes if needed.

Unfortunately, my list is always packed, and I rarely complete more than just a few things on the list, so I'm constantly rolling everything over to the next day, and the next, and the next.

Part of it is probably that my to-do lists are often more of a work of fiction than fact: They're what I would like to be able to get done the next day.  I use Google Calendar to keep track of my tasks now, since I can see them on my calendar and schedule them for when I want to work on each thing, but when I have another task scheduled every half hour, the harsh reality is that I just can't accomplish everything that fast.

I suspect I'm not alone, and a lot of writers - a lot of entrepreneurs - do the same thing.  I've heard that being late all the time is common with optimists, because you tend to optimistically underestimate how long it'll take you to do things or get places.  I think the same goes for to-do lists.  I put a bazillion things on my to-do list every day because I optimistically think (or hope) I can get it all done.

I've seen productivity experts recommend only having a max of three things on your to-do list, but for an entrepreneur that seems unrealistic, as there are always things that need doing.  Yet when I get to the end of my day, I've often accomplished only a few things on my to-do list, so maybe they are onto something after all.

I guess it's too bad Google tasks don't have a separate list for "evergreen" tasks, ones that don't have a separate due date, but still need doing at some point.  A lot of the tasks on my daily list are that kind of thing, but I don't know what else to do with them so I stick them on a day.  If I have time to tackle one or two of them, I do.

Unfortunately, this has the effect of making me feel at the end of the day like I didn't accomplish enough.  Even though I can look back on my day and see that it was busy and full, and realize that I did do some important things on my list, I am faced with all of the things I didn't do and have to roll over to the next day.  It's demoralizing to do it day after day, but like I said, I'm not sure of another way.  And my current method of using Google calendar's task feature is actually helping me stay on task better, so I don't necessarily want to change to a different system.

What kind of list-maker are you?  Are you realistic, with just a few items on your to-do list every day?  Or are you optimistic, hoping you can conquer a long list of tasks, and being disappointed every day when you can't?  How do you handle tasks without a specific due date on your to-do list?