Taming the Procrastination Monster

—Amy M. Gardner

As a kid, did you ever hear a creaking floorboard in the night, and become convinced that there was a fully grown boogieman waiting to pounce out of your closet?  


Procrastinated tasks can become the adult equivalent of monsters in the closet.  You don’t want to admit it, but you see the signs every time you look at your to do list, whether it’s in an app, a spreadsheet, a paper planner, or on a post-it.  Maybe it’s scheduling your annual physical, sending a thank you email, texting your niece, or finding a contractor to finally fix the bathtub.  Or maybe it’s writing an article for a professional publication, filing an amended tax return, getting your job application materials together, reviewing resumes for a position you’re supposed to be filling, or finally cleaning up your office.  

Whatever it is, these tasks lurk out there, popping up to stress you out when you’re in the shower, thinking “I got a lot done today,” or generally feeling on top of things.

And, like the combination of sounds in the night and a child’s overactive imagination, somehow 10 minute tasks fester in our minds until we’re sure we can’t tackle them without an empty afternoon.  

Today, we’re going to help you stop procrastinating and tackle these items once and for all.  The tips I’m about to share are a combination of having read just about every time management, habit formation, and procrastination book or blog post there is, then realizing all of them are helpful in their own way, but none as good as a lot of my own trial and error.  So below, my own spin on six tactics to get every procrastinated task off your to do list: Eliminate, Automate, Delegate, Trade, Time, Calendar.  

First, ask yourself: Does this really need to be done?  If you’ve been procrastinating it, it most likely isn’t urgent (no one has started bleeding from their eyes because of it yet, right?), and maybe it doesn’t really have to be done.  If not, stop letting it stress you out and make a conscious decision to eliminate it from your to do list. Then – and this is important – stop feeling guilty about it and move on.  If the task can’t be eliminated (let’s say the task is making a dentist appointment and you enjoy having teeth) move to the second question.

Ask yourself: Can this task be automated?  You can, for example, set up a standing delivery through Amazon’s subscribe and save service to avoid having to ever think about buying your favorite pens again. Or, as in our appointment example, you could make your next dentist appointment at the end of one appointment. That way you’d never have to think of it again.  

If there’s no way to eliminate or automate the task this time, though, go to question three: Can I delegate this task?  (The order for these three questions is important, because, as Tim Ferriss explains in The 4 Hour Workweek, “Never automate something that can be eliminated, and never delegate something that can be automated or streamlined.”)

If you have an assistant who can do the task and it falls in his/her job description, great.  For those of us who do not have assistants thrilled about doing our personal tasks, this is where we may be tempted to give up, because we think we don’t have someone to delegate these tasks to.  

This is often based on an assumption that we can’t delegate because no one else can do a task as well as we can.  Here’s the problem with that logic:  if the task needs to be done perfectly, that isn’t happening right now . . . because right now it isn’t getting done at all.  Will 80% of the task today be better than 100% in a month after you’ve driven yourself crazy thinking about it?  And what other tasks will have suffered for you to reach this perfection? Second, ask yourself why you are so sure you are the only person who can do the task to the standard that’s required. It is entirely possible with a little explanation, demonstration, and supervision, that you may be able to stop doing a task completely going forward.  

If you have ever used the excuse, “I’m too busy to train someone,” or “it takes longer to train someone than to just do it myself,” I have news for you: this short-term strategy is holding you and your team back in the long-term.

It can also be worth considering whether you can hire someone specifically for the tasks you procrastinate, whether it’s someone off Task Rabbit to run your errands, a virtual assistant, paying your baby-sitter a little extra to add it to her workload, or maybe you have kids who would be willing to do your procrastinated tasks in exchange for extra screen time or allowance.

Assuming there really is no option to delegate, though, then move to my next question: Is there someone I can trade with?  In my case, I have never had a personal assistant or an assistant who I could ask to do personal tasks in anything other than emergency situations.  Yet I often don’t do my own procrastinated tasks myself.

Presumably, your significant other or best friend has a similar list of things they are procrastinating.  The difference is that his or her list doesn’t have the same emotions associated with it as your own does.

Let’s take a real-life example.  I recently received an erroneous bill from the doctor.  I knew the only way to resolve it was going to be calling, sitting on hold, explaining that they must have billed my insurance incorrectly, and resending my insurance card.  I had no desire to spend the time it would take to deal with this.  I also didn’t want to cover their mistake, so I could not eliminate the task.  There was no option to automate it (other than giving up and paying online), and I couldn’t delegate it.

Instead, I traded it with my spouse, who had a list of books he needed to order.  He agreed to make the call, and I agreed to find and order his books. Both tasks took us less time than we had each estimated our own task would take, which brings me to one of the advantages of this approach.  I have a not-very-scientific theory that every time you see a task on your to do list and decide not to do it, you’ve just upped the time you estimate it will take. So if you need to do a 5 minute task on Monday, and look at it each day until you finally do it on Friday, that same task grows from Monday to Friday until you estimate it will take you at least 10 minutes.  It hasn’t actually gotten any harder – it’s just taking up more of your emotional energy and brainpower.  (It’s that monster in the closet phenomenon.)  Think about it – how often have you done something you’d been procrastinating and realized afterwards that it took a lot less time than you expected?

That’s why trading is so effective – the person you’ve traded with hasn’t been looking at that task, letting it grow in their mind.  They just need to do it and get it done and are usually fueled by their relief at not having to do their own pesky task.

This tactic can also be helpful at work, especially if you are on a team doing a project and who does it is less important than it getting done.  You may be able, for example, to trade tasks with a coworker, or trade days you’re doing them if you know that you need a short deadline to avoid procrastination.  As one example, I had a job where any warm body was supposed to appear in court 90 minutes away once per month.  Most people hated this task – who wants to spend three hours traveling to be in court for 10 minutes?  I loved it. I wanted more courtroom experience, and watching other lawyers in front of the judge meant I learned everything I could about how the judge handled his courtroom, and was a better asset for the team when we had significant arguments in front of him.  By being the person with a pulse willing to go to these hearings, I collected lots of favors I used to trade away tasks I was less excited about, like babysitting opposing counsel reviewing sensitive documents.

OK, so what about the tasks you can’t eliminate, automate, delegate, or trade away?  Here, my favorite tool is a timer.  If I have tasks I personally must do and have been procrastinating, I will set a timer for 5, 10, or 15 minutes (usually depending on how much I’m dreading the task).  Nearly 50% of the time, I end up finishing the task before the timer goes off. About another 25% of the time, when the timer goes off, I realize that the task is much easier than I had expected and decide to just finish it.  And in the final 25% of situations, I have made good progress on the task and have much less to do the next day to finish it.  Either way, using a timer can be a great tool to get you moving on something you’ve been procrastinating, whether that task is writing a memo for work or finally wading through that pile of magazines on your coffee table.

Finally, another good strategy is to calendar a specific anti-procrastination time to work through items you’ve been neglecting.  Whether it’s Friday from 9:00 a.m. - 10:00 a.m. or every Thursday from 7:00 p.m. - 7:30 p.m., mark a time when you are likely to have energy and can get yourself to do nothing but wade through long-procrastinated tasks.  That strategy both forces you to work on them, and acts as a built-in timer, because you only have so much time allotted.  (This is made easier if you can enlist an accountability buddy, or even make it a family- or office-wide anti-procrastination time.)

By using the Eliminate, Automate, Delegate, Trade, Time, Calendar approach above, you can get those pesky tasks off your to do list before they grow in your mind and deplete your energy, leaving you more time for the fun things on your list.  Like fixing those creaky floor boards.  

How do you avoid procrastination?

Please share your strategies in the comments below.