1. Group the tasks together. For example, I don’t like calling strangers and asking for information, so if I have to make five of those phone calls (say, for writing research), I do them all in one sitting. This way, I figure, I’ve only had one unpleasant afternoon instead of many. The technique works for writing/sending query letters, too.
2. Set a timer. If writing feels hard, I find that setting a timer and making an agreement with myself (I’ll spend fifteen minutes and stop if I'm still miserable) can often get me over the hurdle of getting started. Then I continue past the set amount of time. (For more on timers, you can also checkout the Pomodoro technique.)
3. Journal. Sometimes it helps to explore why the tasks are difficult. Fear of failure? Fear of success? Journaling about it helps to get to the root of the problem and makes it seem like less of a big deal.
4. Do the most difficult things first (during the day or even during the week), so that the chore isn’t looming. (As Laura Vanderkam says, "Climb your mountains on Monday mornings.")
5. For possibly un-dreaded, but “low return” tasks, Chris Bailey, author of The Productivity Project, suggests scheduling a “maintenance day.” He does chores like cleaning, shopping, and laundry at one designated time (such as a Sunday), so that his other days are more productive.
Do you have any techniques for accomplishing them?