Procrastination Hacks

Ken Soto
The Startup
8 min readJan 21, 2020

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I consider myself a connoisseur of procrastination advice, so I jumped at the chance to attend a workshop recently on the subject. The workshop covered territory I’m very familiar with, but I came away somewhat disappointed. It wasn’t a bad workshop, it’s just that I’ve consumed so much procrastination-related content it’s difficult to find anything new.

But maybe that’s the point. Maybe there really isn’t much more to say about the subject, and maybe the point is that I’m spending so much time consuming procrastination content because I’m putting off doing anything about my procrastination problem. So, I decided to stop all this reading and thinking about procrastination, and just get down to…writing about procrastination!

This can look like a guide to productivity, another subject that I am completely unqualified to opine on (which you’ll see if you keep reading). That’s probably because procrastination and productivity are directly related, in my view. Also, I don’t believe procrastination is a character fault, or a mental weakness, or even a superpower, as some who are looking for a silver lining have claimed. Many approaches to procrastination employ a brute force method, suggesting that the solution is, well, you just need to try harder. I think procrastination is a learned behavior that has roots in other issues related to distraction, focus, and confidence. So my procrastination hacks deal with these issues first as a way to understand and then short-circuit them.

Herewith are my Top 6 Procrastination Hacks:

1. Let your to-do list help you

If you are like me, you have oftentimes created a workday schedule that has an entry that looks like this:

9:00 AM: Work on Project X

While this may look harmless to some, to a procrastinator an entry like this is an gold-plated invitation to the total loss of your morning. Why? Because to a procrastinator’s mind, working on Project X is nowhere near specific enough. We will begin our 9:00 AM block by trying to remember what part of Project X needs attention, then thinking about where we left off with Project X, then looking for that email from the Project X PM, then doing a search for “Project X” in our email app to retrieve the last message that mentioned the thing about the thing…and we’re gone. We are already miles away from the task the needs doing, and there are these other emails that we’ve just seen, and remember that email from last week when so and so said such and such…

The procrastinator’s mind is far too easily distracted to deal with this kind of abstraction. We perform better when the schedule entry looks like this:

9:00 AM: Project X: Resolve mobile UI conflict for onboarding registered vs unregistered users

This gets us right to the problem we want to solve. If the problem is difficult we can prepare ahead of time how we’ll solve it (see 5.) We can improve our productivity even more with specificity: include the directory path to the relevant files, paste a link to the InVision space where the prototype lives, anything that builds an expressway to the work and places guardrails around it is hugely beneficial.

2. Eat the elephant

This one is easy and well-known, but it relates to 1. It’s all to easy to become overwhelmed by the scale of your work, especially if you are prone to a level of anxiety that interferes with getting stuff done. It goes like this:

I need to work on X. X is critically important! So much is riding on it!

X is also so big, there are so many things to do…I should start with this part…or maybe it’s more efficient if I do this thing before that thing…

What part should I start on?! I can’t keep everything in my head at once!

I need to take a break from thinking about this…maybe do some laundry first…

This is the eat-the-elephant example. Eating an entire elephant seems impossible, how could you do it? Well, you’d take one bite at a time...

That’s how your tasks should be put before you. Break all of your projects into constituent parts. Aim to break everything into 15–30–60 minute intervals, so if you’re writing a report, give yourself a chunk of time to collect your data, another chunk to outline everything, another to draft the first version, and so on. Create multiple chunks for things that take longer, but avoid the tendency to enter simply enter “Write Report” into your schedule.

And don’t hesitate to spend a significant amount of time doing this. It can dramatically reduce the anxiety you might feel about starting. And while you’re at it, consider using a Pomodoro timer to clamp down on the concentration and focus. This is one technique that employs a brute-force approach that actually works for me, probably because it feels so small. I can do anything for 20 minutes, even if I end up just sitting in my chair offline, thinking.

Speaking of sitting in my chair…

3. Don’t sit in front of your computer unless/until you absolutely have to.

Related to 1.: I’m a somewhat old-school designer that began my career just as computers became available, so for at least a few years designing meant sketching with a pen and paper, usually tracing paper so that you could duplicate a sketch by dropping a new piece of paper over the first one. As the design process shifted to computers, a particular issue appeared: the tool you use to design also encourages you check the weather, or email, or order lunch. What started as a period of abstract thinking and sketching transforms into a hundred detours only a right-click away. How did this happen?

It happened far too easily. If your pen and paper could enable you to buy cat litter from Amazon you’d do it. But they can’t (yet). So leverage the difference.

Commit to avoiding your keyboard and mouse until you absolutely have to enter text. Start with pen and paper, writing longhand, or sketching, or just thinking or reading. But force yourself to hold off from sitting in front of a screen until you know exactly what you need to use the tool for, and then do just that.

If you need to check email, check your email, then turn away from the computer and do not return to it until the thing you need to do requires it. You might even go so far as to create another workspace if you can, one for reading and writing, sans computer. Yes, there are many apps that can turn off your internet, but that still leaves you with access to a device with far too many uses unrelated to the task at hand. Just step away, completely.

4. Plan what you are going to do today yesterday

Never sit down to work without knowing what you are doing that day. Map out the day’s work the day before, or days before, but never the day of. Why? There are a number of reasons, but some of the best ones are:

Prioritization: Decide what is most important to work on first. When you‘re crunched for time, anxiety builds up and creates a perfect medium for putting something off. Without planning, you’re likely to believe the most important thing to work on is the most stress-inducing project, or maybe the least? Either way, that’s no way to organize your time.

Preparation: You don’t want to launch into something only to realize you’re not ready to answer some questions, or don’t have all of the data or resources needed to work effectively. If you know today what you’re working on next Tuesday you have time to get ready.

Sous Vide your creativity: Plant the problem in your mind days ahead of when you’ll actually work on it. It’s the old best ideas in the shower thing—let the contours of the problem sit in your head on a low temperature, and open the lid every now and then to see how things look. It’s not a stretch to say that most of my best ideas happen when I’m not trying to solve something.

The Observer Effect, but for procrastination: Related to the sous vide, my version of the observer effect is that for some reason, the closer I am to the work, the harder it is to do it. It goes like this: as long as the actual work is in the future, it’s exciting to think about it. When the time comes to actually sit down and do it, the confusion and uncertainty swells. I’ve concluded that this is related to the roots of procrastination mentioned in 6, and the solution is pretty straightforward: while the work is in the future and still exciting, think about how you’ll do it, scribble some notes, and keep the temperature low.

5. Identify the exact moment of procrastination, and expose it.

I’ve studied my own procrastinating behaviors enough to know exactly when I’m likely to stop working on something and drift off to something else. Usually this happens when I don’t know exactly what I’m to do next — if I finish a sentence without knowing what I want to say next, boom: my mind will face the void of doubt and confusion and will instantly look for a distraction. Usually that means Command-T on a browser and a trip to Twitter or a favorite blog to see what’s happened since my last visit 4 minutes ago.

I’ve had success when I notice the exact moment this happens and called it out. Sometimes I’ll just say to myself “nope” or I’ll click the close X on the browser tab instantly after opening it. Is this insane? Opening a tab and milliseconds later closing it? Of course it is! But it’s part of the journey of surfacing behaviors that are so ingrained that they’ve become habitual and hidden.

6. Recognize the root of procrastination

Credit for this one goes to many authors who suggest that the root of procrastination is not a sign of cognitive deficiency (although for some that is a possibility). No, for most people procrastination is rooted in issues just outside of the actual work. We procrastinate because we fear what is on the other side of finishing: exposure. If I finish this article draft, or these logo sketches, then I’ll have to show them to someone and be judged for my work. They’ll now have concrete proof that I don’t know what I’m doing! Better to not start at all so I can avoid the shame and humiliation of being exposed as a fraud.

Of course this is irrational, but that doesn’t make the feeling go away. In my experience, procrastination is deeply connected to imposter syndrome—that feeling that everyone is an expert at something, except me. I am somehow the only person who is unqualified to speak out, to do the work, to provide value to others. Yet research indicates that most people experience some level of imposter syndrome. Those people who appear to glide through every professional challenge? They’re also imposters, at least to themselves. How is it possible we’re all imposters? We’re not. We all have something to contribute—the ones who seem so successful are simply pushing past the inhibition to be public, most likely because they have more practice at it.

This concludes my own practice session. Hope you found it useful.

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