Being a todo-list aficionado, I keep items for every aspect of my life on my lists. Even the enjoyable things, like painting, poetry, or writing prose. In fact, exactly because they are enjoyable but require overcoming an initial barrier to start, I found it very useful to have them on my todo-list. If I put an item like “write a poem” on my todo-list, the probability that I actually start writing it is significantly higher than when I just plan to do something nice after work. It works similarly well for sports or any other endeavor. Besides, there is a double mental satisfaction to have a creative product finished and to strike the item through on the todo-list or mark it as done. However, there is also a downside to the list-business, as I have noticed the last couple of months. Having between 20 and 30 items on my daily todo-list, I will emotionally pick always the ones, which seem to be least trouble. These are most likely not the ones, which are most important or urgent to do. If there is an item, which indicates the slightest doubt about how to do it or poses a certain level of difficulty then it is postponed indefinitely, unless, of course, there is time pressure from a deadline. Thus, at the end of the day, I will have done maybe 15-20 easy items and will have left the hard ones on the list for the next day, that is, I removed the sand, but left the rocks.

I remove the sand but leave the rocks.

The satisfaction of doing easy tasks and striking them through is much higher than starting and eventually finishing one difficult item, which might take about 5 or 10 times that long. In the done-economy of todo-lists more strike-throughs are simply more valuable. An alternative approach, which some some people seem to advocate, is to prioritize items and give important tasks a higher rating. Consequently, you have to force yourself to work on the high priority items first. Giving more difficult items a higher rating, however,  does not seem to work for me. I tend to be simple minded. The higher priority given to more urgent or important but harder to do items, will not make me do them more eagerly. Emotionally, I feel that one item is one item, independently of its level of difficulty.

In the done-economy more strike-throughs are simply more valuable.

Thus, trying out several different approaches, I have found three strategies, which seem to work for me. I have been using all three of them, but I haven’t tested them thoroughly and long enough to give a final verdict as to which one is the absolute best.  I have a strong favorite, though:

1. force myself to do the difficult items nevertheless, preferably first.
2. time-chunking or time-boxing.
3. chunk the items down, so that they do not appear to pose a threat to my feeling of being in control.

I have tried the first strategy in the past with very little success. Unfortunately, I seem to find any valid excuse not to do the item if I perceive it as too big, too scaring or too overwhelming. Sometimes, especially when I am under pressure, I can and will overcome this reluctance, though. But after completing those scary, intimidating tasks under pressure, I always feel empty, down and weakened since I fought a double battle – the one with the task and an internal one with my inner resistance and fear. After having made this experience many times, I was looking for methods, which would leave me more invigorated after finishing off the big tasks, or at least not completely exhausted.

The second approach is time-chunking or time-boxing. Instead of tackling the big item on your todo-list at once, you just force yourself to work on it for a specified amount of time, for example for 20 minutes or half an hour. After that, you are free to change to something else or reward yourself.

When I use the time-chunking approach (half an hour work on the unpleasant item, then you can do whatever you like from the todo list) I seem to be able to work on it, even to the extent that after the period of time has elapsed I voluntarily continue working on it. However, deciding to do time-chunking also requires quite some mental efforts to force myself to start, which I admit, I often lack. Very often it is also demotivating to see the same item on your todo-list day after day, working on it half an hour to an hour at the time, with no real feeling of advancement that would be reflected on the todo-list. You would write “Task X – 30 minutes” every day in your todo-list, strike it through after you’ve done your share, only to add the same task again the next day. Although you certainly move ahead in the task, looking at your todo-list, it just does not feel like that.

The last approach is item chunking. In this approach, you try to break down the item into as many sub-tasks as possible, Each of these sub-tasks should be so easy and so quick to do that none of them should evoke any kind of psychological resistance. Any of those tasks should be as easy as pie and not take longer than 10-15 minutes.

Using the same example above, instead of adding “Write a poem” in my todo-list I would chunk it into several sub-tasks, each requiring about 10 minutes or less:

• brainstorm topic for poem
• make a mind map for poem topic
• write down some initial ideas about poem structure
• decide on poem form
• write first verse
• write second verse
• write third verse
• write fourth verse
• read poem aloud and listen to flow
• polish the rough edges
• type poem in poem-file or journal

Thus, instead of having the single item “Write a poem” on your todo-list, you have broken it down in eleven sub-tasks, all of which, seem relatively easy to do and do not evoke any particular fears, at least if you have written any poem whatsoever in the past.

I have found that most tasks on my todo-lists can be broken further down. Especially the ones, which seem to pose a certain difficulty and uneasiness. This is very encouraging. It requires initially more work to think the task through, to break it down and to write all the separate sub-tasks down and it will create many more items on my daily todo-list, however, adhering to the strike-through law of the todo-list economy, all of them are now much more manageable and don’t create any resistance. All tasks are easy to do. And that leads naturally to two pleasant outcomes:

1. You get more tasks done.
2. Of those tasks done, many of them are from the important and urgent categories.

Thus, in the end, you will be more productive. You will feel that you are not postponing the important tasks any longer, only because they are too big or daunting to do. Break all the tasks down to the smallest possible sub-tasks, and you will see that even the biggest pièces de resistance, the big items, which you have been postponing for the longest time, will simply melt away with many small easy to do sub-tasks.