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I have recently started using the Pomodoro technique for workflow management. I like it, it provides a consistent workflow.

One thing I have noticed is that high "activation cost" activities seem really difficult. By this I mean tasks such as programming or detailed writing where it seems I must spend a good portion of each time period reconstructing in my mind the previous work I had done.

Is this normal and an intended part of the system? Or does this get easier after using the technique longer?

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One thing that I have found that the pomodoro technique trains in me is the muscle which works on exactly what you are concerned about. Initially I was concerned that when programming, I would be in the middle of a large refactor or stuck in the flow and then I would get bumped out of it by the end of the pomodoro coming and doing my rest interval.

After a couple of weeks programming using the pomodoros for focus, I found that it was much easier to remember where I was when I came back from a rest break. I understand that this is part of the technique, that you are also training yourself to be able to take short breaks without losing the place that you are at.

When I got about a month into using pomodoros for focusing on tasks, I've found that it not only helped just after a rest break, but also when I was coming back the next day or on a project which I had not worked on for a while. I would be able to remember my position even though I hadn't touched the project in a while. Part of it was that I knew that if I was done with my pomodoros for a day, I would leave a note or clean up quickly before quitting as well.

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After playing around with this, I've found this to be 100% true on my thesis writing. Taking a complete 5-minute break somehow hardly affects me as it seems I just jump right back into things (which is magic and the more I do of this the faster I seem to get back?) –  enderland Nov 26 '12 at 19:35
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I use Pomodoro intermittently. I find a couple of things happen when I'm using it. First, high activation cost activities are almost always of a size that need multiple pomodoros to complete the task. Anything that's more than 4 pomodoros I break down to smaller tasks. It takes practice, but can always be done. Second, the 5 minute break between pomodoros isn't enough to lose my context, as long as I choose my break activity with a little care. I may go for a quick walk, or empty the garbage can, or some other physical activity that doesn't flush my mental context entirely. Getting back up to speed for the next pomodoro then doesn't take very long.

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Try looking for continuity between Pomodoros. Some examples:

  1. Write an outline as the first pomodoro
  2. Write a "mini todo list" with 5 minute tasks as part of your task and cross out as you go
  3. If writing code, write a failig unit test first so you have that for context
  4. If writing documentation (or non-code), write notes at the bottom for thoughts you have that you want to expand on

What all these have in common is that they let you just start in the next Pomodoro. Once you start, you will likely recover a lot of that state more easily.

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I found a good way to deal with such tasks: In the first pomodoro of my day I write a todo list and, for each element of the todo list I write down exactly what I will do.

One could argue that it's not possible to know exactly what you'll do in advance. I think it's not true, but there is a workaround also for this: when your plan changes finish your pomodoro and use the next to write what you'll do.

I kind of borrowed this technique from GTD, it lets you free your mind from remembering what you need to do next, just read what you need to do, this shortens a lot your bootstrap time.

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Switching tasks with a high cognitive-load is difficult with Pomodoro (for me), so establishing a task-switching routine before (single or multiple) Pomodoro sessions on such tasks helps me.

You could, of course, change the amount of time you work and take breaks...I adjust the timing depending on the kind of work I am doing.

And, depending on how long you have been using it, you might find that over time the breaks become less of a problem both in terms of getting back into the work after a break and in taking advantage of the break to let your subconscious work on the problem.

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