Conquering Your To-Do Lists Before They Conquer You

Compartmentalized Trays by Roo Reynolds

Compartmentalizing your tasks can make them much, much easier to handle effectively.

Caroline and I are both severe to-do list addicts (Caroline perhaps even a little more than me).

This can be both a blessing, and a curse. On one hand it makes it very easy to organize our tasks and have a good plan going forward for what we need to be working on. It gives a nice shape to conquering our goals, like a step-by-step quest list in a video game, and takes a lot of the uncertainty and nebulousness away from what we’re working on.

On the other hand, it provides an easy platform upon which to load so many tasks that we inevitably break under the pressure of all of it. After all we’re both very ambitious people – giving us a blank sheet to list everything we want to do is like setting us lose in an Indian buffet, we’re going to load our plates up like we haven’t eaten in weeks. As a result our to-do lists crush us and we wind up being even less productive than if we hadn’t bothered with them at all.

So what’s the trick to making effective to-do lists that help you get things done, but don’t grind you into the ground? Compartmentalization.

Compartmentalization and Chunking

Compartmentalization, or chunking as I like to call it because it’s easier to type and reminds me of the Goonies, is basically taking your insurmountable pile of tasks and placing them in easy to conquer compartments or breaking them down into manageable chunks.

This method of managing your to-dos has a range of benefits:

  • Less Procrastination – A common cause for procrastination is the discomfort caused by facing a task that looks utterly daunting. We’ve talked about this a bit when discussing timeboxing, when you have a huge, impossible looking task in front of you it’s all too easy to deflect and put it off until later. It’s a natural expression of pain avoidance and is hard to fight on your own since it’s so deeply wired into our behavior.

    By breaking down those big, scary tasks into smaller, easy to manage chunks it makes it less scary and easy to overcome the urge to procrastinate. It’s easy to put off cleaning the entire garage, but if all you have to do is tidy up a single shelf it’s hard to put off. After all, that’ll take like 5 minutes. When you add up a bunch of those little tasks over a week or two though, suddenly you’ve cleaned the entire garage.

  • Harder to Burn Out – Chunked to-do lists make it much, much easier to avoid burnout for similar reasons to why they help avoid procrastination. Breaking up those enormous looking tasks make it feel a lot more like you’re working on a wide variety of things rather than one big project. Slogging along writing a book may feel like an endless task, driving you to burnout since you don’t feel like you’re making progress. Focusing on completing chapters instead gives you tangible markers of progress and keeps you from feeling overwhelmed.

    Compartmentalization like this also helps you avoid the type of overloading we always fell prey to. Breaking things down into small chunks make it easier to see things in the big picture, and when you can do that it’s far easier to prioritize. What really needs to get done immediately / today and what can wait for a day or two?

  • Improved Energy Management – This ties in a lot with the burn out benefits above. I’ve talked in the past about how energy management can be a lot more important than time management. We all get 24 hours, and it’s great to try to spend them efficiently, but if you feel like shit all day your best laid plans gang aft agley.

    Chunked lists make it easy to schedule in time to relax and recharge without feeling like you’re being lazy or slacking off. You know you’ve gotten everything you needed to get done completed, and at the same time have plenty of time to recharge and tackle the next day fully energized and guilt free.

Weekly/Daily Lists – My Favorite Method for Chunking

While there are a lot of different options for ways to chunk up or compartmentalize your to-do lists (and I encourage you to play with others to see what you like) I am personally very fond of the Weekly/Daily list division.

I’ve found that in addition to all of the general benefits listed above, Weekly/Daily lists also help me be far more proactive about my tasks by providing me with a small glimpse at the bigger picture. Trying to cram everything on only a daily to-do list always made me myopic and short-sighted – having an entire week to play with gives me the perspective to arrange things out ahead of time and further avoid my tendency to overload myself.

I’ve also found that keeping the division at days and weeks rather than further out, like having a monthly to-do list for example, is short enough to not fall victim too much to Parkinson’s law while still being long enough to give me the freedom to strategize my tasks out into the future.

So how do you use a Weekly/Daily list?

Either at the end of the week, or at the beginning of the next if you prefer that more from a psychological standpoint, list out all of the things that you need to get done in the coming week. In general, I prefer to prioritize larger projects here over smaller things, but there’s totally a place for little to-dos like ‘mow the lawn’ or ‘buy groceries’.

At the end of each night, or again first thing in the morning if you prefer, write down all of the things you need to get done the next day (or that day if you’re the morning planner type). These can be either smaller chunks of the larger weekly tasks, (e.g., if a task for this week is write five articles then a daily chunk of that task might be write one article, or come up with five article ideas, etc.) or individual small tasks that needn’t be chunked like mowing the lawn.

You focus only on your daily list each day, and when you’ve finished it you’re done. You can spend the rest of the day relaxing.

Tips For Getting the Most Out of a Weekly/Daily List

While it’s a fairly easy process to build and use weekly/daily lists, I’ve found in my time experimenting with them that there are some finer points that make them more useful and make the whole process a little easier.

  • Monthly Reviews – Like I noted above, having a monthly to-do list on top of a weekly & daily one tends to wind up being more problematic than helpful. Aside from encouraging falling into Parkinson’s law it makes it easier to procrastinate, and sometimes makes it harder to focus in on the things that are really important in the immediate sense. That being said, looking out a month ahead can give the benefit of having a clear long term goal to work toward.

    The solution is to have a single monthly review day, similar to a severely pared down version of our annual review process. On your monthly review day you take a retrospective look at the previous month, figure out what went well and what didn’t, and then set some lose targets for the following month to serve as a foundation or inspiration for your weekly lists.

  • Avoid Scope Creep – If you’ve never worked in an industry like web or software design, scope creep is when you’re nearly finished with a project for a client and they send you the dreaded, “Hey, could we also do x,y,z?” Your two week project becomes a three week project, then a four, and a five, and so on.

    When it comes to weekly/daily lists, avoiding scope creep means not allowing yourself to add anything to your daily lists on that day. If you finish all your day’s work before noon, that’s it. Don’t add anything else. The minute you give in to the urge to add just a couple more things the sooner you’ll be building an infinite to-do list again, and that’s what we’re trying to avoid. There will be days when you need to make adjustments, but it should only be for things that are extremely urgent or emergencies. If you finish your list, it’s time to relax.

  • Use a Today/Tomorrow Board – Sometimes things do need to get pushed back, either because something else came up or you just over-scheduled yourself. I like to manage this process by keeping my daily lists on what I call my Today/Tomorrow Board.

    My Today/Tomorrow Board is just a small marker-board that I have divided in half horizontally. In both the top and bottom sections I’ve written ‘Today’ and ‘Tomorrow’ in one of the corners. In one box I have a little mark next to ‘Today’ and in the other box next to ‘Tomorrow’.

    In the half with ‘Today’ ticked, I write my daily list for that day. In the other box, ticked ‘Tomorrow’, I write the next day’s tasks as I think of them. Then when the day’s finished, I can move any tasks I haven’t scratched off my list down to the ‘Tomorrow’ section as well as whatever else I determine I need to do the next day. The next day I just erase my tick marks and switch them, so yesterday’s ‘Tomorrow’ box becomes today’s ‘Today’ box and the other the new ‘Tomorrow’ box.

    While there are certainly other ways to manage things like this, I’ve found this system works particularly well for me since it’s always sitting on my desk. I can glance up and get a quick snapshot of what else I have to work on for the day, as well as what I’ll be working on tomorrow. It also makes it easy for me, when I remember something spur of the moment that need to get done, to add it quickly to my tomorrow list before I forget.

  • Don’t Drift from Your Daily List – Lastly, it’s extremely important not to let yourself lose focus on your daily list, the things you have set to complete today. It can be tempting to start thinking about the rest of the week, what other things need to get done, etc. Once you do this though it’s easy to completely drift away from what you actually need to be doing – the things on that day’s list.

    Once you’ve chunked everything out, forget that everything exists except for that day’s list. Nothing should occupy your concern except for the things you’ve laid on the table before you for that day. Personally, having my Today/Tomorrow Board has been a big help on this front for me as well, as it’s psychologically comforting to me to being to place something on the ‘Tomorrow’ list and say “Ok, it’s written down for tomorrow, I know it will get done then, I can forget about it.”

Finding What Works for You

These methods for compartmentalization are my personal favorites, and I’ve gotten a lot of benefit out of them, but everyone works a little differently. I strongly encourage you to try them out along with some other methods to see what fits your personality and work style best.

If you’ve found any others you particularly like, or discovered any other tips for making the weekly/daily lists even more effective, leave a comment and share with everyone! It always helps to hear about other people’s experiences.

Photo Credit: Roo Reynolds

Adam is a former English teacher turned personal trainer and writer. He’s addicted to learning, parkour and martial arts. In addition to being a voracious bibliophile Adam’s fascinated by anything related to health, fitness and language. When not studying or training he can usually be found curled up with a good piece of fiction. You can e-mail Adam at Adam@RoadtoEpic.com