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I have found that my todo lists work great for three cases:

  1. Simple things that have a very specific due date (e.g. call Chris at 3pm, pay credit card bill by January 15, etc.)
  2. Things I would like to do but don't have to be done (e.g. organize the closet) and don't have a due date
  3. Short, "continuous" tasks (e.g. scan some of the pages in my filing cabinet) - I refer to this list when I have a few minutes free

The one type of task I'm having a problem with is something that has a definite due date but is more of a "project" - something that will take, say 6-8 hours. If I set the due date to the actual due date, then I risk being surprised by it and not having time. But if I set it earlier than that, I'll just continually reschedule it. One suggestion may be to break it up into small items and stagger their due dates, but I'll just keep postponing them, thinking that I want to do it all at once.

Say, for example - doing your taxes. You wouldn't put a due date of the deadline, because if you started working on them on that day, you wouldn't have enough time to complete them. So what do you do? Just pick an arbitrary earlier day and either complete it then or hope that the reminder will keep it on your mind so you do give yourself enough time to get done by the real deadline?

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I can think of two approaches. I strongly prefer the first one:

Approach #1 - make smaller tasks

Many tasks can be made smaller. Having one 8 hour task isn't terrible, but a lot of big tasks are going to get lost and impact your planning. I think doing your taxes is a great example of how to subdivide a task. For me, doing my taxes has the following steps:

  1. Make sure w2's and 1099's come in - due first week in February
  2. Get tax booklet from library - due mid to late February (I'm old fashioned and like to write out my taxes on paper as a first draft)
  3. Take out folder where I collected info for year (like charity receipts) and calculate taxes - due late March
  4. Enter e-file info and confirm matches my numbers - due late March
  5. E-file or print/mail taxes - due early April

Approach #2 - list as one task with time remaining

I have a list of things to do at work with columns for priority, due date and estimated effort (amongst other things.) I sort it by due date then priority. This is because most of the things on the list don't have due dates. (otherwise I'd sort by "tasks due in next week" and "all others". I don't let this list get more than one page to keep it easy to scan my current tasks. If I have more than one page, I move some to a parking lot of things that I'd like to do someday. I revisit this list once a week. If I see an 8 hour task, it will be a reminder to start. I also have a column called "next step" on it to force myself to think about starting.

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Ok, thanks - I was thinking of something like the first approach. I guess my question then is how do you decide on those due dates and how flexible are you with them? Do you pick them pretty arbitrarily? Do you choose them at times you think you'll be free? I'm specifically thinking of the situation where I get a reminder alarm, and I'm supposed to immediately start working on it (maybe that's not reasonable and I'm being too rigid). Is it ok to postpone them in this case, as long as it's not for too long? – Jer Dec 28 '12 at 15:12
Jeff: I pick them based on when I think I will do them. I then review my tasks for the week/day. So they are pretty flexible. I also know when the real deadline is. But I'm not a procrastinator so this isn't a problem for me. I also don't do them immediately. I like to plan my day and not respond to a series of artificial "urgent" items. – Jeanne Boyarsky Dec 29 '12 at 2:21

I suggest you better maintain a pending list and sort it by priority. Whenever you find free time just check your list and go to work !!

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Basically it is a problem of balancing between short term goals V/s long term goals. My experience is the the long term goals unfortunately get a back seat. One suggested approach to this problem is: At the beginning of every month pick up some of the long term projects which you want to complete during the next month. Make a list of these jobs. Then at the beginning of each week pick up some the jobs from this monthly list and put them into another list, the list of weekly jobs. Now everyday when you are planning your daily TODO list try to accommodate some these weekly list jobs. This way it reminds us of long term projects on a daily basis. Of course you will end up in breaking these long term projects into shorter sub projects as suggested by @Jeanne Boyarsky.

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Then planning requires a lot of time for a single task, I feel it is easier to just keep aside an entire day to finish it off.

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