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Suffering from to-do list defeat? Here’s how to take back control

This time management expert offers surefire tips for getting out from under, boosting productivity, and regaining your sanity.

Suffering from to-do list defeat? Here’s how to take back control
[Photo: Andrea Piacquadio/Pexels]
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In my attorney days, I had a to-do list for each active case, which I carried with me from meeting to meeting like security blankets. Truth be told, I loved my to-do lists. But with working 12-plus-hour days and feeling like I never accomplished quite enough in the day, I actually thought I was bad at time management.

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Back then, even on days I rocked it and completed a huge brief, I’d go to cross the brief off one of my many to-do lists, only to see the 48 other things I didn’t get done. My pride in completing my big project deflated, even though there was no way I could have gotten the whole to-do list done in a single day in the first place. That unwarranted feeling of never quite keeping up (much less getting ahead), and therefore never quite being good enough, is what I call To-Do List Defeat.

To-do lists make us think we should be able to get it all done now, and when we don’t, we feel bad about ourselves and unmotivated to get up to do it all over again tomorrow.

The good news is there’s another approach to managing tasks and time that helps you set realistic expectations and actually meet them—something the never-ending, all-taunting to-do list fails at. This approach helps you feel accomplished about what you got done today instead of feeling bad about what you didn’t, and realistically couldn’t, do.

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Block your tasks

When you’re looking at your to-do list, every item looks the same. Each takes up a single line, but some tasks take 15 minutes while other projects take 15 hours. When using a to-do list, every time you sit down to figure out what to do next, you have to think through how long each item will take, what you have time and energy for right now, and what you need to prioritize.

Instead, to create realistic expectations of what we can and should fit into a single day of work, we need to tie our tasks to the amount of time they’ll take to complete. By blocking time for each task in your calendar, it’s much easier to protect adequate time for each task, prioritize your tasks based on their deadlines and importance, and get an objective sense of how full your workload is.

Emotionally, since you’re now realistically planning what you can do, you feel accomplished at the end of the day—a big improvement over that constant To-Do List Defeat.

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How to avoid the common problem of underestimating

The most common frustration I see when people first start time-blocking is underestimating. When you’re all excited to try out time-blocking, it’s a pretty big bummer when you quickly realize you haven’t blocked enough time to work on something. I get the frustration and have been there too, but this is actually a great sign: It explains how unrealistic your expectations have been and why you’ve felt overwhelmed. Now you know what to work on.

Understand that this is likely the first time you’ve tied tasks to time in a concrete way, and understand that you won’t be a pro at it starting off.

To help alleviate the frustration as you learn, I have two strategies to help you increase the likelihood you’ll block sufficient time.

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First, break down your project into bite-size steps and calendar each of those individual steps. It’s common to think at the outset something will take you just 10 hours but quickly realize once you break down all the steps that it’ll take more like 30 hours. Not only will this approach help you more realistically estimate a project’s time commitment, but it also helps you build a game plan of how you’ll accomplish everything over time, which is huge for reducing stress and delivering high-quality work product.

The second strategy is when you’re blocking time for a task, overestimate how long you think it will take by two times when you’re starting. It’s better to overestimate and come up with bonus time than to underestimate and get behind.

The best part of this practice is that it forces you to be realistic. You may end up with some initial frustration about how much less you can get done in a day than you want to, but it’s the reality you need to face so that you can make the right adjustments. Getting realistic will help you deliver quality work product, be more reliable at work, and actually go to bed feeling proud of what you got done today and calm about what’s on tap tomorrow. The frustration is worth the benefit and is certainly better than the overwhelmed feeling of To-Do List Defeat.

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Say Goodbye to To-Do List Defeat

Give time-blocking a whirl. When you time-block everything in your life, you see how it all fits together and how it can all get done over time in a realistic way—even if you take that break tonight. It helps you feel confident about your ability to show up in your roles in the ways that you want, and given how hard you work, you should go to bed feeling proud of how you showed up today and confident you can do it again tomorrow.


Kelly Nolan is an attorney turned time-management consultant who helps working women and entrepreneurs take control of their time and improve their work-life balance.