There are a few things together that have helped me, and they all happen before the task goes into whatever planner system I’m using. First, the initial monster list is not my to-do list, it’s just a way of getting things out of my head (I think it’s David Allen who uses the term “brain dump”?) I don’t have to do everything that ends up on the list, and most of it doesn’t have to happen right away. So when you write it out, try to see it as clearing your head, and keep in mind that writing it down is not the same as committing to do it. That comes later.
Second, I assess whether the things on my list are really tasks, or if they’re habits. Forming habits is a different problem, and I set those aside to address elsewhere.
Third, I decide on a prioritizing system. I’ve combined a couple to arrive at my own personal one, which is: (1) physical/emotional health (this includes finances); (2) relationships & commitments; (3) related to my goals (for this one, I have to choose 2 or 3 clear goals I’m working towards right now); (4) Everything else. You can experiment with your own priority list, and tweak it over time, and the more self-reflection you do, the better it will be.
Then, I look at everything that’s priority #4, and asking myself if I really need to do it. A lot of the time, these are things that I want to do, or think it would be nice to have done, but they’re not that important. Get rid of them. Sometimes they’re there because I think they’d be fun-- but then why stress about it? I put those on a “fun menu”, which is totally separate from my to-do list.
From there, I can look at stuff from the other priority levels and ask, “Is this really necessary?” and “Is this really necessary right now?” What is each task costing you in stress, versus the benefit of having it done? Haggling my cable prices down may fit in priority 1, but is the money I save worth the stress of seeing it on my list? I’d call that a “later problem”-- “Later problems” get their own list, which I look at only when I’ve addressed my “Right now problems”.
(I think I got the phrasing “Later problem” and “Right now problem” from a joke a friend made, but it’s SO effective for me. For some reason, saying to myself, “That’s a later problem” is much more stress-relieving than saying “That’s a problem for later”)
So by then, I’m left with a much smaller list, of things that are both important, and need to be addressed now. Those are the only ones that get planned/scheduled/put on my to-do list. I decide when to do those based on deadlines and looking back at my priorities. When I have time for more stuff, I can go back to my “later” list, and use the same priority system to add in a manageable amount of additional tasks.
And voila! A much less intimidating to-do list!