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How do you deal with difficult tasks, which take long to complete? My problem, for example, are emails which require a lot of writing or research. They are not the main core of my work, and usually are not urgent, but sometimes they are important and I have to write them (so I can't skip this task). If I decide to make them first thing in the morning...well, I will do nothing half of the morning because they paralyze me. If I do them last thing in the afternoon, sometimes I just postpone them the next day . Sometimes, after long time, I reply just with one line, renouncing to my elaborations.

I think I will just live with it, and go directly to one-line replies. Sometimes I have this situations with different tasks, so I wonder if there is any theory on how to deal with this kind of problem? I remember the big stones in "seven habits..", but I can't apply it to this case.

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up vote 4 down vote accepted

Something that helped me a little while ago was to realise that there was no real relation between the dread of the task, and the effort required to do the task...

For example there have been tasks on my todo list that look like "email X about Y" that have sat there for nearly a week with me dreading them everyday. But it turns out that tasks like these only take 10 minutes to do. So now when I have a task I'm dreading I

  1. Recognise that I'm dreading it (often this is the hardest part)
  2. Remember how easy dreaded tasks often turn out to be
  3. Give it five minutes doing and see where I am

Often it turns out that the task you are dreading is like seeing something out of the corner of your eye when walking down an alley late at night: scary, but generally nothing...

Also has a really interesting take on this, to quote:

My to-do list for the project of publishing my first e-anthology of short stories:
Obtain a professionally designed book cover
Format document in line with style guide
Sort out PayPal
Sort out PO Box for press releases
Write sales blurb
Write copyright notice and appendix
Create landing page for e-book purchasers
Research e-book pricing and decide on a price
Publish e-book
Note how each of those seem perfectly reasonable and pretty detailed in some cases. When I was writing the list, I knew that some tasks would be relatively quick to execute and more straight forward than others. What I didn’t realise was that there were other tasks I had to tackle before the project could be completed. What it should have said was:

Get over reluctance to ask my busy best friend for help  
Obtain a professionally designed book cover
Format master document in line with style guide
Sort out PayPal
Sort out PO Box for press releases
Figure out what the essence of the anthology is
Write sales blurb
Write copyright notice and appendix
Create landing page for e-book purchasers
Get over extreme block about charging money for my creative writing
Research e-book pricing and decide on a price
Push past the fear of failure
Publish e-book

(it's better formatted in the oringinal - and I think it's a fantastic way to frame the problem)

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So the final advice is " time I write a to-do list, I’m going to take a moment to see how I feel about each task, rather than a purely logic-based, practical appraisal of what needs to be done." I am not sure if awareness is enough (I'll try), but it describes exactly what I mean by "dreaded tasks" – laika Nov 2 '12 at 16:04
Ha! That's a much better way of putting it than I did! – Joe Nov 2 '12 at 17:09
I just copied from the link! – laika Nov 2 '12 at 21:01

Pomodoro technique & breaking tasks down into to smaller subtasks helps me get through this type of work. Tasks that leave me brain-dead, I leave for the afternoon instead of morning, so I can go home when I am finished. I also block them all into half of one day per week. Spreading them out into something like one hour a day usually doesn't work for me, I just deal with them all in once chunk so I can move on.

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+1 In my personal experience, after getting used to the rythm of pomodoro technique, I found that tasks that left me brain-dead existed no more. I hope that one day this will work the same also for you! – Gabber Oct 29 '12 at 15:53

I'd go with pomodoro technique as suggested by Dina. Yours seems more a problem of time and feeling management than one related to the difficulty of task. I tailored this approach for you. I think it's going to work!

First step:

  • Start a kitchen timer (25 minutes) and make suer you hear its ticking
  • On a sheet of paper create a LIST with all the mails you need to reply to
  • for each one think quickly to what you are going to write and research

    • keep the action plan in your mind or, even better, write it down.
    • think of how much time you will spend in answering the email. For the ones that require a 25 minutes effort you are ok
    • group the ones that are less time consuming.
    • Divide in 25 minutes chunks the longer ones carefully planning what you are going to do in each time chunk.
    • The important part for you: you say that usually you research a lot for an answer and then trash away your work and reply with a one liner. Track carefuly your objectives: if you accomplish just two of the three research tasks you planned for your email and you planned well you can still use them
  • If you are finished with your list, take the plans for every single mail and see if it fits or edits are required.

When the timer rings rest 5 minutes


  • start the timer (25 minutes)
  • get the first email in the LIST you made
  • follow what you have written on the sheet for that email
    • (you write before so you don't have to think after, this removes a lot of stress)
  • RING
  • rest 5 minutes
  • repeat (if you are not finished with the email keep on this one)

This allows you to manage stress in many ways: getting tired in doing something is due to lots of factors: unclear objectives, fear of failure, context switching and the consequent need to spend energies to focus again on your task.

Another important thing: don't leave the hard work for the evening! You are more tired, thus it'll probably take longer to finish the hard work => you'll feel more tired!

Last word: Pomodoro technique gives good results even at the beginning. Even if you feel tired after the first day, stick with it at least for two weeks.

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All my answers on the productivity stackexchange are ridiculously biased, but I think the "One Must-Do Task of the Day" system works beautifully for this:

That's from Mark Forster's Get Everything Done blog. The idea is to set up a commitment device where you always pick one task (maybe a dreaded one) that you have to get done the next day.

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ALWAYS do the worst things in the morning then everything else seems much better through the day! Check out this interesting article on why its productive to do the dreaded things first thing in the morning.

Eat The Frog!

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Link only answers aren't very useful - as the link may break. Can you please update with at least a summary. – Rory Alsop Dec 21 '13 at 14:25

Pomodoro is brilliant! That is a really simple tool. But... it's rather difficult to follow Pomodoro rules if you have to do some kind of conceptual or creative work. So I use Kanban. I also break tasks down into small parts. Then, I write each task on a card and put it on my board. You can choose between traditional (physical) and online board. I prefer webbased version (Kanban Tool) I recommend you two articles for further reading about Kanban:

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Something no one has mentioned is looking at the consequences of not doing the task. Is the most objectionable part of it vital and are the consequences worse than the process of doing the task? I'm wondering if this has more to do with overcoming a lack of motivation than with a method for making them more bearable.

Is there an alternative like doing only a part of the task, which while not as good in the long run would mean you are more likely to do it now? Part of changing habits is small steps and implementing a new set of habits is hard work. You are more likely to succeed if your imediate goals will over time slowly build up to the goal of doing all the dreaded subtasks involved in the dreaded task.

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I have tried for years to use the Pomodoro technique and it works for a few days, then I just find myself ignoring it. I've tried a lot of things to try and stay motivated, currently, the best tool I've found is - an early stage company who encourage you to break everything out into very detailed as you accomplish small things you get a sense of progress. Not perfect, but is working well for me now. In a month I'll report back as to whether it's still proving useful. :-)

The book "Drive" by Daniel Pink is a great read if you have time, about what really motivates people...and a key thing is feeling a sense of accomplishment for all of your efforts, not just completing the big things.

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