4 Reasons Your Task System Might Be Failing You (And How To Fix It)

When maintaining a task system feels like more trouble than it's worth, here's now to turn the tables.

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Photo by Mindspace Studio on Unsplash
Photo by Mindspace Studio on Unsplash

Think about your phone for a second. Do you see a graveyard of abandoned task apps, full of stuff you didn’t do in the past? Or perhaps you’re more of a physical list-maker. How many notebooks have you got lying around with 1/2 finished lists? Perhaps you’re a post-it person; post-its litter your desk, but you can never find the one you’re looking for, and you’re always worried the important ones will get lost.

If you’re nodding along in self-recognition, feeling that your task system or to-do list is a little bit futile, read on. I want to share with you the primary reasons I see that cause people to get frustrated with, and abandon, their task systems. And I’m going to share a simple fix for each of these problem areas.

Reason 1: It’s a list, not (yet) a system

If your task system is just a big long list of all the things you have to do, then it’s not, in fact, a system. If, when you look at your task system, you’re left asking yourself “what should I do next?”, it’s not a system. It’s a list. And a list often serves to make us feel bad about what we aren’t doing, instead of helping us get the right stuff done. Your list might have lots or organization, many folders, it may be exquisitely color coded. There might be a complex prioritization structure. But if, on a day by day, hour by hour, basis, it’s not absolutely clear what you should be working on, then it’s not (yet) a system.

The Fix

Assign clear next actions and realistic next action dates to all your tasks. When will you actually do the next step for any given task or project? Not when would you like it to be done, or when would it be good to be done. When will you actually do it? Based on the time you have available.

The list is the “what”; it becomes a system when you are able to assign a realistic “when”.

Reason 2: It’s not (yet) your single source of truth

If your task system is not your single source of truth, where all your tasks live, then it’s really hard to prioritize. If you’ve got a task system, but your email is also full of to-dos, and you’ve got a notebook, and post-its, and your name assigned in some Google docs somewhere and a whole brain full of tasks that aren’t written down anywhere at all, well, then it’s no wonder it’s easy to ignore your list.

It’s not complete and there are a lot of other things competing for your attention. The more lists you have, the more places where tasks live, the harder it is to prioritize. You can’t trust that everything is in your system, and that you’re making the right prioritization decisions because everything isn’t in your system…yet. And when we don’t trust our system, we get stuck in “emergency scan modality” and we often make the error of doing whatever is in front of us, because we can’t see how it fits into the system as a whole. We confuse the (seemingly) urgent, with the important.

The Fix

  1. Define your task funnels. Where do your tasks come from? Email? Slack? Your calendar? Your brain?
  2. Define your process for each funnel. For each funnel, define how you’ll get tasks into your system, consistently. (Many task apps have email integrations that make it very easy to turn an email into a task in 1 click. Many have browser extensions that make it easy to add tasks from anywhere. My favorite task app, TickTick, has both of these features AND the ability to enter tasks by voice.)
  3. Do a BIG brain dump and then regularly brain dump into your system. Work to build the habit of writing things down. If you think of it, it goes in the system. Because if you don’t, then you’re bound to think of it again, at an inopportune time.

Reason 3: It’s not (yet) realistic

Ok, let’s say you’ve got all your tasks in one place, and you’ve got next actions and next action dates assigned, but it still feels like you’re sweeping water. You push things day after day. Or worse, leave them in an overdue status that only increases your anxiety. You’re so close to having a system that works really well for you! But, you’re simply too ambitious on a day to day basis. You’re giving yourself more than you can handle on any given day, based on the time you actually have available.

The Fix

  • Become a task realist! If you’ve got aspirational items on your list for today, you’re setting yourself up for failure. We don’t simply “find the time”. Look at your calendar, figure out what you’ve actually got time for, and only assign those things for today that you are actually going to do today. If you miraculously happen upon some “extra” time, then you can always pull something from tomorrow’s list and do it today. (Imagine how awesome that will feel!)
  • Start time blocking. Let your calendar guide you. If you start blocking off on your calendar what you plan to do and when, you will quickly start to see you have less time than you had imagined. And you’ll therefore have to get more ruthless (and realistic) in your prioritization.
  • Learn your “estimation multiplier”. Humans are terrible time estimators. (Me included!). But I find that most people have a pretty consistent ratio by which they are off. I’m a 1.5x person, personally. What does this mean? Well, I pretty much always think that writing this blog post will take me an hour. And in reality, it always takes me 90 minutes. So now I just block 90 minutes on my calendar. Whenever I think something will take me 30 minutes, I block 45. 1.5x is my multiplier. How did I figure this out? By tracking how long I thought things would take me, with how long they actually do.

Reason 4: It’s a repository, not (yet) an engine driving your day

Do you often say to yourself: “I just don’t have time to update my task system” or “Updating my task system is too labor intensive”. If “updating your task system” is a task in your task system, you’re fighting a losing battle.

Instead of thinking of your task system as a repository, you want it to be the engine that drives your day. I often describe my task system as a living, breathing friend of sorts that’s always with me, propelling me forward, letting me know what I need to do, and when.

The Fix

Update your task system in the moment. Do a task, update the task, move onto the next task. Repeat.

When you update your task system in the moment, as you are doing a tasks, the benefits are threefold: 1) Your task system is always up to date, with very little effort and 2) You save yourself from having to think about something twice and 3) You get to watch your task system getting shorter throughout the day, which is very satisfying.

If you update your task system after the fact, well, now you’re doing extra work that will take even more time. You’ll be wondering, “did I send that email to Sue, or is it still in drafts?” and then you’ll have to go check before you update. It’ll take more time, and feel like extra work and overhead. You’ll question the value of your system.

Instead, keep your task system open and ready all the time. Make sure it’s always open as a tab in your browser and available on the home screen of your phone. Ensure you have the Chrome extension installed and any other add-on’s that make it easy to access anywhere. Remove friction and make it easy for yourself.

Did I miss anything? Is your system breaking down for a reason I didn’t mention above? Let me know!

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