How to Get Stubborn Items Crossed Off Your To-Do List

Get Organized: What to do When Your To-Dos Just Won't Budge

When I started writing this article, I had two tasks on my to-do list that just wouldn't budge. I put them there in December. One had to do with a home insurance policy, and the other with moving some retirement funds. Neither one will ever be critically important to complete. Neither has a real, meaningful deadline. They are things I really should do, but I never want to do.

Most of us have stubborn items like these in our to-do apps, those tasks that never seem to get done, such as taking a suit to the dry cleaners or getting the dog groomed. Nothing bad happens when we don't do them, so we don't do them, even if our rational brains know they should get done.

What can you do to knock these chores off your list? A few options come to mind, which I'll share here. Plus, I'll tell you what tricks finally helped me check off my own unmoving to-dos.

Get OrganizedDo It First Thing in the Morning
Many productivity enthusiasts swear by tackling those little annoying tasks first thing in the morning. The idea is to get minor tasks off your plate early before you get wrapped up in more important work, such as your hardest tasks, email, meetings, and anything else that will distract you.

This trick is great if the task takes less than two minutes and it's not time- or place-dependent. If you make a habit of banging out any task that takes less than two minutes before you even open your email program, you could see a lot more movement on your task list.

When a task takes longer than a few minutes, or when it can only be done during a certain time or place, this two-minute rule doesn't work. The two things I can't seem to get done, for example, both need to happen during U.S. Pacific time, and those hours don't line up with my morning overseas. I need some more options.

Make Someone Else Do It
When at first you don't succeed, give the job to someone else. I'm kidding with that line, but I'm not kidding about delegating tasks that heretofore you have been unwilling to complete on your own.

Quite frankly, I'm terrible at delegating. I have a hard time asking for help. I worry about inconveniencing people. I like to be in control. Maybe you feel the same way.

How can people like me get better at delegating? For starters, we can think through a list of potential delegates even before we decide whether to delegate the task at all. Don't rule out colleagues, family members (including responsible children of an appropriate age), babysitters or other caretakers, and, in some situations, neighbors. It also helps to put the shoe on the other foot. How would I feel if, for example, my neighbors asked me to sign for a package or let the cable guy in if they couldn't be home to do it? If the task fit with my schedule, it would be no problem. These simple thought experiments all make delegating seem like a reasonable option.

One of my chores is actually perfectly suited for my partner to do, although come to think of it, he was supposed to do it initially and didn't, so I delegated it to myself! As to my financial task, only I can do it because I'll need to verify my identity and sign some papers in the process.

Create a Reward
As much as I don't want to do my two tasks, I can think of a few things that I'd like more, like a few hours at a spa or an extra $15 in my monthly coffee shop budget. Setting a reward for yourself can increase motivation.

Research suggests that motivation is higher when we don't know our payout. For example, in one study, participants had to complete a water-drinking task. They received either $1 or $2 for getting the job done. When they knew they would get $2, about 43 percent of the subjects completed successfully. When they didn't know whether they'd earn $1 or $2, 70 percent finished.

How can you use rewards and uncertainty to your advantage? You could write down two possible rewards for getting your to-dos done and then, once they're complete, flip a coin to see which one you get. Or you could ask for help in creating randomness in your reward. "Honey, here are two envelopes full of different amounts of cash. When I finally get my task done, I want you to give me one of them and put the other back in the bank."

I have mixed feelings about using food as a reward because often it can conflict with other goals, like losing or maintaining weight. I also don't know how much I want to be motivated by food. But I had some exquisite German, chocolate-covered marzipan that I had been saving for a special occasion, and I remembered it while writing this article. I decided that if I took care of the insurance situation I would treat myself to them alongside a cup of my favorite coffee. And what do you know? I got that sucker done. One down, one to go!

Temptation Bundling
Another rewards-based motivation technique, called temptation bundling (as described by Katherine Milkman, associate professor at The Wharton School, The University of Pennsylvania), is particularly useful for stubborn to-dos that are recurring. An example is getting a Pap smear test, which should be done annually.

Temptation bundling is the act of giving yourself a reward while you're in the act of doing the task you don't want to do, rather than after. In Milkman's research, she gives college students access to best-selling audiobooks only while they're at the gym. Her research showed that students who got the audiobooks went to the gym more often than a control group, and they continued to go more often even after the audiobooks program ended. The students had created a habit that was positively reinforced.

So let's say you hate going to your annual OBGYN appointment. You could bundle a guilty pleasure, such as reading trashy magazines or enjoying a double-chocolate milkshake (if you're okay with food rewards), and allow yourself to indulge while you're in the doctor's waiting room. The two actions you bundle need to happen simultaneously, although in my example, I'm going to say being in the doctor's waiting room is close enough because you can't do much of anything while someone is swabbing your cervix.

My tasks were not recurring ones, so they weren't set up for temptation bundling, unfortunately.

Create a Consequence
If positive reinforcement doesn't cut the mustard, maybe negative consequences will. Would you donate a dollar to your least favorite political party for every day you don't do your task? Most of us would need a seriously hard-core friend to make sure we made good on our promise if we were to try and use negative consequences to drive positive behaviors, but it's not impossible.

There's a famous story of a woman named Zelda Gamson who quit smoking when her friend created a contract with her. The contract said if Zelda smoked ever again, the friend would donate a huge sum of money to the Ku Klux Klan. Zelda never smoked another cigarette. The consequence was too great.

I don't think negative consequences would work for me. They're really tough to choose and even tougher to implement. Plus, every day that I don't get my tasks done, I already feel bad about it. Why would I want more negativity? Still, they might be good incentives for some.

Break It Down
Another reason people get stuck with tasks they just can't complete is that they just write down the wrong task. They lump together a series of related tasks instead of breaking down the larger project. The same thing happens with goals. If you want to be successful at reaching goals, you need to learn how to break them down into their component parts. Each part has to be a single, actionable, quantifiable item. That's why "jog for 30 minutes today" is a better task than "lose five pounds." Losing five pounds is the goal, not the task.

My financial task, it turns out, is actually three or four tasks—possibly more. In fact, I have no idea how big the task truly is. The problem is that I wrote down "Investigate retirement account rollover" rather than the first step that I actually need to take. The first step is to gather the paperwork and phone number. Every time I thought about my task, I said to myself, "Argh! I don't even know where the paperwork is!" So finding the paperwork should be the first task in this series.

The second task is to call the bank. The third task is to ask about my options. The fourth step is, well, I'm not sure yet. It depends on the outcomes of the other steps. Clearly I've got some more work to do here, but after examining my chore, I have a better idea of how to break it down into manageable parts. That's progress!

The Final Tally
As I mentioned, I did accomplish one of my tasks by enticing myself with a little marzipan. I'm so relieved that it's done. The other task is still hanging, but at least now I've taken it apart and reorganized it into multiple tasks that seem less daunting. Hopefully, it and its component pieces will be off my list soon. I hope this article can help some of you make progress on your stubborn tasks, and I invite you to tell me about the techniques you use in the comments below.

1 Comment
  1. Reply Amanda 22.08.2016 at 13:08

    I’m such a perfectionist that delegating is not an option for me, at least not when it comes to really important issues. What I do is plan everything out and get it over with step by step, finishing one task before starting another one.

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