You know the kind of to-do list item I'm talking about -- the ones that linger at the bottom of your list as you churn through less horrible tasks above it, the one that seems to laugh at you every time you look at your list, the one that causes a sinking feeling in your stomach every time you tell yourself, "Today is finally the day!"
Maybe it's just mind-numbingly boring. Maybe it involves unpleasant confrontation. Maybe you secretly think you just don't have the skill to accomplish it. But whatever the reason, we all have at least one or two to-do list items we particularly hate ... and put off forever.
So, how do you finally conquer your dread and finally check that sucker off your list? Author and entrepreneur David Kadavy has suggestions.
In a recent Medium post, he urges readers to listen to the horror the long-neglected bottom of their to-do list stirs in them. Those dusty items are down there for a reason. If you could accomplish them with your usual routine, you would have done so already. Checking them off once and for all requires you to take extraordinary measures. Kadavy shares ideas. Here are a few of the best:
Do it in another location. Transferring your contacts from your old system into your new software, proofreading that bone-dry 200-page report, or similar donkey work is just too boring to face in a boring location. Could you talk yourself into doing it if you took yourself out to your favorite coffee shop or local park? How about if you were stretched out on your couch in your pajamas?
Bribe yourself. It works for toddlers, and it can work for you, too. "An unpleasant task can be bearable if you have something to look forward to," writes Kadavy. So tell yourself you can knock off for the day right after you finish, or call a friend and suggest happy hour (or bike riding or shopping) as soon as you're done with your most dreaded task.
Make it easier. If it's fear of failure that's holding you back, acknowledge your fear and try to make the first steps of the task way easier. "Even if you're trying to write an article, just writing some bullet points of ideas can be a good start," notes Kadavy.
Set a timer. This is also the favorite technique of Instagram founder Kevin Systrom. "If you don't want to do something, make a deal with yourself to do at least five minutes of it. After five minutes, you'll end up doing the whole thing," he's suggested. Kadavy agrees it's far easier to face your most hated tasks if you know you can bail after just a few minutes (and that momentum will often carry you through to the end once you get going).
Document your process. Is your hated task something you might have to do again? Then add value to the horror by taking careful notes about the process, making things easier for your future self and keeping your mind occupied while you complete it now. You might even be able to document the task into non-existence. "After you've refined your notes a couple of times, now you have a process document that you can use to hire someone else to do the task!" notes Kadavy.