How to Build a To-Do List that Doesn’t Make You Miserable

By Zoë Randolph, GC4W Thought Leadership Contributor

I love lists. If you were to unearth my grade-school diaries, you’d discover, among the dramatics, crushes, and uses of two “g”s in “excellent,” a broad collection of aspirational day plans, ranging from the legitimate (“write a story;” “wrap Emma’s birthday present”) to those (”take shower;” “brush teeth”) evidently included solely for the joy of checking them off.

It’s a habit I’ve taken with me ever since, through my color-coordinated high school homework planner to my current array of physical planners, white boards, and digital productivity tools. Failure to plan, is I’ve found, a non-starter for me. Without a list to work through, I become overwhelmed to the point of inaction, not sure where to direct my energy.

But to-do lists can cause as much harm as good, especially if you’re prone to being hard on yourself. Planning our attention fails for several reasons, including:

Humans are laughably bad at predicting how long things will take

In fact, we’re so bad that there’s a name for it: “the planning fallacy.” The planning fallacy refers to our universal tendency to underestimate how long it will take us to perform tasks even when—and here’s the kicker—we know previous efforts have taken longer than we thought they would.

This habit, which we might kindly classify as enduring optimism, means we’re almost always wrong when we try to block out time in advance. (Sure, I told myself when I started writing this morning, I’ll have this blog post written in an hour.)

There’s nothing wrong with dreaming big, but when we routinely come up short of our expectations, the experience is a wearing one. We write ourselves an absurd task list each morning, only to be disappointed each afternoon when we inevitably come up short.

We aren’t the same person every day, and shouldn’t expect ourselves to be

Your washing machine’s delicate cycle takes a standard amount of time each time you run it, just like it’s programmed to. Surrounded as we are by standardization, it’s natural to see ourselves along the same lines as we do our appliances. But for better or worse (I would argue, for better), we are not machines.

Some days we’ve slept well, some days we’re groggy. Some days, when light floods through the window and your neighbors aren’t making any noise, we feel almost electric with focus, creativity, and inspiration.

Rather than punish ourselves for our natural variation, we’ll do better to take each day as it comes and work with the tools we have. This means adjusting our focus based on what we’ll be best equipped to achieve in a given day, rather than attempting to rigidly stick to pre-determined checkboxes.

Life is inherently unpredictable

We all know the saying: “Even the best laid plans…”

No matter how fastidiously you map our your hours or how aesthetically pleasing your planner, you’ll never be able to account for the entropy of the universe.

Your CEO needs something—now! Your kid gets sick. Your dishwasher malfunctions and starts gushing water on to the floor. From the catastrophic to the good, (a surprise call from an old friend; a piece of positive news) the only thing you can plan for is unpredictability.

When I was employed in tech, I slogged through my daily to-do lists without much thought about how they could improve. I always hit my deadlines, so I figured things were as good as they could get. It wasn’t until I began my freelance career that the potential (and conversely, the drag) of a to-do list became clear. Without a single set of priorities handed down from on-high, it was entirely up to me to structure my days and ensure that I hit the milestones I’d set for myself. The more I paid attention to what made some days successes and other days duds, the more I saw that my lists held more power than I could have imagined.

Here’s what I’ve learned about building a to-do list that actually works for you:

Plan weekly, then break it down

Instead of getting lost in the details of the day-to-day, I like to work backwards from my biggest goals (for the year; for the month) to think about how I should structure my week. After setting my top objectives for the week, I structure each day in alignment with both what I need to do and what I feel most able to.

If I’m feeling sluggish, for instance, I might prioritize more mundane tasks like putting together invoices, editing a document, and the like. When I’m feeling more peppy, I put more difficult, creative projects at the top of the pile. Sometimes, of course, you have to battle through. But the more you can minimize it, the better.

Leave ample space around deadlines whenever possible

The only way you can prioritize as you please, of course, is if you’re ahead enough on your work to choose. By leaving padding around deadlines, (which often necessitates setting firmer expectations with those around you) you’ll be better able to maximize your productivity based on what you want to do, not what you have to do.

Accept that you’ll never get everything done

However much our subconsciousness may debate this, writing down everything we think we must do won’t enable us to get it done.

Between life and work, there’s an infinite list, and no amount of time-management hacks will make it a manageable one. (For more on this, take a read through Oliver Burkeman’s Four Thousand Weeks: Time Management for Mortals.) The question, then, is not how you’ll get it all done, but what you’ll do in the first place.

Whether it means saying “no” more often or letting go of your need for perfection, I’ve found it useful to set a cap on the number of major tasks I commit to in a week. If something unexpected gets added, something else has to go.

Create a daily “done” list

It almost sounds silly: What’s the difference between checking off a task or writing it down after the fact? And yet, I promise you, there is one. To cross off an item on your list is to meet your expectations. You said you’d do it, and you did. While there is sometimes an accompanying burst of happiness or relief, I’ve found that my most prevalent feeling is neutrality. Yep. Check.

When I also write down what I achieved, perhaps with a little more detail, (was their an unexpected obstacle, perhaps?) I feel a sense of pride. That sense of achievement in turn creates a positive feedback loop that spurs me to tackle the next thing and get the next win.

Most interestingly, I’ve discovered that the same principles apply to the never-ending list of things I need to accomplish outside of work. Prioritization, celebration, and pickiness have made every aspect of obligation both more manageable and more satisfying—without sacrificing the number of boxes I check.

About our thought-leadership contributor, Zoë Randolph.

Zoë Randolph worked in marketing for nonprofits and startups before becoming a full-time freelance writer and editor. She covers history, culture, travel, and career from her adopted home of Montréal, Quebec, where she pretends to understand French and enjoy winter. You can keep up with her at

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