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Break It Down: Why Small Tasks Make for Big Wins


I walked past a dumpster chute on my walk to the office today with a sign taped to it that said “please break down your boxes.” I think we should tape signs to our laptops that say “please break down your work.”


The pull to check email a hundred times a day, or organize your desk for the fourth time, or add the fillets to your model before you’re even ready to do a draft analysis, is a pull to feel like you’re making progress. And progress is our greatest motivator. It confirms to us our agency and autonomy within life.


But making progress on the hard things is hard, and let’s be honest, almost anything worth doing is hard.


There are fundamentally two flavors of difficult tasks, and they both have weak points we can exploit to be triumphant. There’s the “I don’t want to do this because it’s uncomfortable” difficult task. And the “I don’t want to do this because it’s going to take a long time” difficult task.


The reason the first is difficult is straightforward, avoiding uncomfortable things is historically an adaptive strategy, so we’re programmed not to want to do them. Avoiding discomfort = less chance of failure = less chance of dead. I say historically because this isn’t adaptive in most contexts these days.


The reason the second is difficult is a bit more nuanced. Something taking a long time isn’t inherently difficult, what’s difficult is continually renewing your internal motivation to finish a task when you don’t see any progress.


So here are some ways to shift our approach to each of these flavors of so called "difficult" task.


For the first, we can reframe our discomfort with a new mindset, and a new habit loop. The habit typically begins as “I feel discomfort, so I procrastinate to avoid the discomfort, and I am rewarded with a temporary easing of the discomfort.”


We can change this sequence to “I feel discomfort, which is my cue to get excited, I take one tiny action in the direction of the discomfort, and I am rewarded with a feeling of triumph (which eases the discomfort).”


This is easy to write about, and while it’s technically simple to do, it’s not at all easy to do. In fact, it’s really darn hard. So you can start with the key thing — noticing the initial feeling of discomfort. Maybe work on just that one piece for a week. “I feel discomfort, I NOTICE that I feel discomfort, I feel excited that I noticed!” Once you’re consistently noticing, you can start to take that tiny action, building on your excitement.


For the second flavor, let’s circle back to progress being necessary in order to stay motivated.


This is why we love to-do lists with a million tasks on them, they make us feel like we’re getting things done. This is only a problem if we’re filling the lists with unimportant things. So instead of putting lots of irrelevant things on your to-do list, you can break the important tasks down into smaller and smaller pieces, so you get that feeling of accomplishment and progress frequently, while making actual progress.


If you’re the type that gets sucked into the “planning your work” vortex, where you’ll spend hours making the perfect to-do list as a way of avoiding doing the actual work, I have a slight modification to help you side-step this trap.


Instead of breaking the work down explicitly, you’ll break it down implicitly.


Your small scale tasks will simply be “work on XYZ big important task for 15 minutes.” And then put however many of these you want on the to-do list, say 4. Each time you complete a 15 or 25 minute Pomodoro, you get to check off that you finished a task, which gives a feeling of concrete progress, which provides motivation to keep going. This “virtuous spiral” can be very real, not just some elusive catchphrase.


This second strategy, of breaking big things into small pieces, is a great approach for either kind of hard task. Because as the individual to-do’s get smaller, the level of discomfort goes down proportionally, and the impediment to action with it.


You start to breeze through each of those small tasks, picking up momentum as you go, and eventually you’ve completed that “big gnarly difficult task” without ever feeling like it was hard.


So as the sign says, “please break down your work.”

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