Noey Jacobson
Content Strategist

Ah…procrastination. The enemy of productivity. The killer of dreams. In a world of unprecedented distraction, how do we defeat this persistent foe?

I’ve always been a productivity nerd. I love tinkering with project management systems, email strategies, and to-do list templates–anything to get an edge in getting stuff done. So, my tendency to procrastinate, despite all of my efforts on the productivity front, has always been a thorn in my side.

I have lost count of the methods I have employed over the years to overcome procrastination.

For a while I was a strict adherent of the “Pomodoro Method.” This involves setting a timer for 25 minutes, working diligently for those 25 minutes, and then taking a 5-minute break. After four 25-minute segments, a longer break is allowed. And for a while, this really helped me get my head into the game—until it didn’t!

I’ve also used elaborate incentive systems. “If I finish writing this section by the end of the month, I will treat myself to my favorite pasta!” Sometimes that works well. Sometimes, I just go ahead and order the pasta anyway.

An Endless Stream of Hacks

When it comes to productivity hacks, there are endless varieties. Here’s a selection that I’ve culled from the internet:

• Limiting email checking to specific times in the day (usually twice a day)
• Using software to block unproductive websites/apps during work hours
• Communicating your own personal deadlines to others as a way of generating accountability
• Switching up your environment—like moving from your home office—to see whether a change of scenery inspires action
• Running a “productivity dash,” in which you work on a task for an almost comically short amount of time—say, just one minute—as a way of generating momentum towards further action

The Limitations of Hacks

But here’s the thing about these hacks. They work great…for a few days. Or a few weeks. Or maybe even a few months. But then they stop working. The procrastination habit invariably takes over. And then it’s on to the next hack. This can be exhausting. It’s akin to relieving the symptoms of procrastination without curing the actual disease.

But there is a way to cure the procrastination “disease” at its root. Doing so, at first, is more painful than addressing the symptoms of procrastination, as hacks do. But curing the disease is more effective, more sustainable, and perhaps best of all, more likely to restore a sense of fulfillment and excitement to the work that you do.

The Two Questions

When you find yourself procrastinating, you can really boil your response down to two key questions. These two questions require some reflection, and reflection takes both effort and courage. But the reward for pursuing that line of questioning, can be massive.

Question #1 — What worthwhile outcome is this task in service of?

This question is particularly helpful for those mundane or annoying tasks. When confronting such tasks, you must find a way to re-frame that task as part of a larger outcome that really matters. It can help to take out a pen and paper and actually write the task in the context of the outcome. The short time it takes to do so will save you hours. The key here is to watch out for the “have-to-do’s” in your life and then to think about how they could be re-contextualized as something you’re really committed to, something that truly matters to you.

Here are some examples:

• I have to do my taxes → I’m committed to the financial viability of my family
• I have to fill out this performance review for my colleague → I’m committed to providing feedback that can help my colleague grow and allow us to be successful in our work together
• I have to clean out all that junk in the living room → I’m committed to creating a peaceful, enjoyable home environment for my family

This slight shift in how you perceive the task often breaks the paralysis.

What if you find it impossible to “zoom out” and connect the task to a larger outcome worth committing to? Well, that itself is an important red flag that is worth getting curious about! Maybe your gut is telling you something about your priorities and revealing a need to renegotiate that agreement (with yourself and others counting on you).

Question #2 — What am I afraid of in completing this task?

This question is particularly helpful for “scary” tasks. The idea is that we procrastinate something that we are actually afraid of. It’s a modern version of the “flight” instinct. We lean away from the fear. But in this case, we’d be better served by “leaning in” to the fear and getting really curious about what is causing it.

Let’s say you have to write a business plan for the start-up you’ve been working on as your side-hustle. But you’ve been putting it off for weeks. This is a time to get curious. What are you afraid of? “Well, I’m not capable of writing a good proposal.” Really? You’re not capable? Say more. “I don’t know how to write one.” Ah, you don’t know how to write one. What specifically do you not know how to do? “I just don’t understand the format. I’ve never prepared anything like it. I wouldn’t know where to start.” Great. We’ve gone from “I’m not capable” to “I’m not familiar with the format.” “I’m not capable” is way scarier than “I’m not familiar with the format.”

What can you do about the latter? Can you talk to your friend Beth who started a business and ask her about how she prepared her proposal? “No! She’s gonna’ think I’m an idiot!” Ah, okay. Scratch that. Can you spend 15 minutes browsing Amazon for books about creating a business plan? You don’t even have to start reading it yet. Just order the book. “Um…yeah. Yeah, I can do that.”

A lot of people find that this is all it takes to generate some momentum. Wins beget wins. You get the book, you read a little, and suddenly, the task doesn’t seem so far out there or as scary as you once imagined. Fear—and therefore procrastination—is often rooted in the unknown. The only thing to do, in that case, is to make the unknown known!

Forget the Hack—Ask the Tough Questions

I don’t mean to discount the usefulness of an occasional hack when you’re looking to kickstart you work. But the next time you find yourself procrastinating, consider confronting the issue on a more fundamental level. What outcome really matters here? What are you afraid of and avoiding? It may be an uncomfortable inquiry at first, and it may require you to slow down first in order to speed up, but it’s an inquiry that will pay dividends long into the future.

 

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