Saturday, April 20, 2013

The Joys & Challenges of To-Do Lists

I love lists.  Activities such as organizing, planning, sorting, setting goals, and checking off boxes are immensely satisfying to me.  Because of that, keeping a to-do list is essential for me.  I discussed how I use to-do lists a bit in my earlier post on my productivity system, but I've been thinking a lot about to-do lists lately so I wanted to discuss them again in more detail.

My To-Do List System

Because I have such a love of planning and organizing, I don't have just one to-do list, but an entire system of to-do lists.  While I used to keep just one to-do list, as my list grew and I started working more with goals, I needed to refine my methods.  Although I feel fairly happy with how I use to-do lists today, my system is still definitely a work in progress.  That said, here are the different levels of to-do lists I use:


  • Giant To-Do List of Doom - A multi-page list of every single thing I want and need to do, from the small to the large.  I only compile this once a year, because it's really messy and overwhelming and looking at it more often than that would just stress me out.  But I use it because seeing everything in one place helps me to get a clearer idea of where my goals, passions, and areas of interest are.  (I talk a bit more about this in my earlier post.)
  • Categorized, ordered lists - From my Giant To-Do List of Doom, I group everything into several categories.  The categories themselves are whatever seem like the best fit for me; last year, I had eight different categories, this year, I had only six.  (That's last year's Blogging list that you see above.)  I also take this time to begin to break down some of the larger items on the giant list into smaller, more manageable tasks.  Finally, I order each categorized list according to priority, which allows me to easily see what needs to be done next.  These lists live in my planner and I add to them throughout the year and periodically rewrite them, removing items that I have completed and revising the order of the remaining items.
  • Month list - This is a new list that I've just started using in the last month.  It addresses the problem I had that even with my categorized, ordered lists, I still had difficulty deciding what particular tasks I should be working on in any one week or day.  (It's difficult because I have many different projects on the go at once, and very few of the things I do have hard deadlines.)  My month list consists of the top items from my categorized lists, as well as other tasks that aren't on those lists (things like cleaning, writing individual blog posts, etc.).  I break everything down into small sub-tasks, and order it all according to when I'd like to get it done by and how important it is.  This really helps me to focus on doing what is most important first, and helps to reduce procrastination.

With all of these lists in place, it's easy for me to select my Big Rocks of the week and my Most Important Tasks (MITs) of the day - I simply choose the top tasks from my Month List, and I can feel confident that these really are the most important tasks for me to be working on in that day or week.  Although the system may sound complicated when I write it all out, it really is simple once I have it in place.  I may need to spend a bit of extra time planning at the end of the month, but I actually end up saving time because I spend a lot less time planning any individual day or week.  None of the lists are set in stone, and I can and do change them as circumstances in my life change.


Challenges of To-Do Lists

My main challenges with to-do lists are overestimating the amount of things that I'll be able to get done in given time and underestimating the amount of time that I need to accomplish any one task.  I guess this is more a challenge in my life generally and not really with to-do lists in particular, but it results in a list full of items that I feel behind on.  I hate feeling behind, but if I could learn to better assess how long I'll need to accomplish different tasks, then I could avoid the problem arising in the first place.  If you have any tips based on how you've dealt with these issues in your own life, I would really appreciate them!

The other challenge that I used to have with to-do lists was simply feeling overwhelmed by them.  I've dealt with that by breaking my list down into categories (which replaces one large scary list with several smaller, less scary lists) and by ordering the items in each list according to priority.  When my to-do list is in order, I don't need to worry about all of the items on it, I just need to worry about the one or two items at the top of the list, and I can trust that those tasks are the ones that are most the important.  It sounds simple, but it really makes things a lot easier!

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Do you use to-do lists?  Do you keep just a basic list, or do you use any methods similar to those I've discussed here?  What are the joys and challenges of to-do lists in your life?

11 comments:

  1. Heather, I ran some errands today that I estimated would take a half-hour. They took about 80 minutes. Yet, when I was a sales manager in a tiny company, my sales estimates for the following quarter were, if my memory's okay, within actual sales by, maybe, plus or minus 20%.

    The difference, I think, is my sales estimates were regarded with a lot more gravity (relatively) by my superiors and colleagues than my wet-thumb-in-the-wind guess about doing neighborhood errands. Money and reputation were at stake in the former case. [BTW-my fastidiousness about sales estimates didn't mean much in the long haul. The company owner was suffering legal and marital problems, and eventually closed the business.]

    So if you're struggling with overestimating and underestimating in your to-do lists, Heather, er, uh, you're not the first. Nice post. Jack/Ohio

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    1. I've noticed that I tend to be better at estimating how long things will take for both shorter tasks and tasks that I enjoy doing more. Longer tasks that I don't enjoy doing as much are the ones that I underestimate the most - probably because I'm subconsciously wishing that they were shorter! (Now that I've written this, I'm thinking that maybe I should try breaking those tasks up more into smaller sub-tasks...)

      And as you said, I think that having other things at stake, especially those that involve other people or how other people perceive us, can help as well. I know I was much better at this in university, when I had more hard deadlines and wanted to get top marks on my assignments.

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    2. Yeah, Heather, I'm thinking military intelligence, weather forecasting, economic forecasts---all activities where you may have to fight your own psyche to get an accurate prediction. That tip you give yourself about breaking a disagreeable task into subtasks sounds good. Jack/Ohio

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  2. Hi! I have been reading through your productivity posts and feeling inspired! I got a binder and a bunch of scratch paper and have been designing every calendar and form I can think of possibly needing. I guess I will see which ones stick. As for your trouble with estimating time, have you considered tracking the time it takes you to do various types of tasks? I have never set out to do that for its own sake, but I sometimes use a 'timeboxing' technique for getting projects done and I get to see how long it takes me to do certain tasks as a result.

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    1. Thanks so much, Gaby! I am honoured to have been an inspiration :) I have been thinking about tracking the time it takes me to do different tasks, and I think I probably will do that. I suspect that it will be an eye-opener! I like having hard numbers to work with, so I think doing that will be very helpful for me.

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  3. I am a huge fan of to-do lists, and pretty much have been my whole life. I'm currently experimenting with just using the basic reminders app on the iPhone, which is easy. The big plus is that it's always with me and it's simple to add another item to the never ending list. I like to sort my lists like you though, so I still end up writing a paper list with tasks taken from reminders, for a specific day or project.

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    1. I don't own a phone so apps like that aren't an option, but I can see that going digital would have some advantages. Maybe one day I'll have the opportunity to try something like that out, but for now paper certainly works well enough for me. Thanks for the comment, Millie!

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  4. So impresive, and inspiring as well. Trying to have a system, something similar to yours, will be my To Do for the next months…

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    1. Good luck with that, Armando! My own system is definitely still a work in progress, so I may be sharing updates as I fine-tune it.

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  5. Does your to-do-lists have the approx time for how long each item should (or you think it should) take? Writing down how much time each one takes helps the next time with the planning!

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    1. Thanks for that, Hanna! I'm actually working on my list for next month right now and I've started to do that already. It really helps me to see the difference between what I want to do and what I realistically have the time to do. I'm sure the more I do it, the better I'll get at estimating the time.

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