If Your To-Do List is Impossible, You’re Doing it Right
Although I write about creativity and productivity for a living, my to-do list is a nightmare. Every day, it’s about a page long with 40 to 50 items. There are categories, subcategories, incremental tasks. Do I check everything off my list every day? No. And that’s the entire point. My list is about the urgent, everyday things, but also about the larger scale, capital-I-Important things I don’t want to lose sight of.
It’s a mess but it’s an inspiring mess. If you keep the bigger possibilities visible — through, yes, staring them down every morning — you remember what all the smaller tasks are in service of. Here’s how to start a whole new to-do list that includes everything you really want to do.
To Do a Great Big Thing, Break It Into Tiny Daily Things
Here’s how to discourage-proof those big dreams
Start with the moonshots
If 2020 taught us anything, it’s that the future is unpredictable. Many people are taking advantage of the turmoil and disruption to their daily routines. You or someone you know is likely at the beginning of a career change, or decided to go back to school, or move to a new city. These big gestalt-shifting goals are like shooting for the moon.
Even if the moonshots don’t feel tangible right now, know this: They deserve to be on your list. Otherwise, every morning you’re staring down a list of “respond to emails,” “schedule afternoon Zoom,” and “follow up with accounting.” Not exactly inspiring stuff.
You can and should think beyond your immediate tasks. One helpful question to ask yourself is, “Where do I want to be in six months?”
To Discover Your Goals, Imagine Your Perfect Day
My life is better because I’ve done Barbara Sher’s ‘Perfect Day’ exercise every year
Catalog your ‘phantom tasks’
One reason we are all so easily distracted from our priorities is because of “phantom tasks.” These are the things haunting the fringes of our days. We don’t account for them in our calendar or to-do list, yet they suddenly pop up and completely co-opt our attention. Maybe you don’t usually think to include “check in with the kids’ Google classrooms” or “pay the dogwalker” on your to-do list, but they are tasks that have to get done and take up your time. Or else these “open loops” lurk in our subconscious, taking up psychic space.
These distractions are preventable, but only if you recognize they exist. Shine a light on all of them. Today’s tasks, next week’s tasks, the “one day soon” tasks. You’ll organize them in a second. And don’t worry about the impossibility of making them all happen. The key is getting them out of your brain.
Organize your list, organize your mind
Before doing my own overhaul, my list hopped around from apartment-related tasks (steam-clean the carpets!) to non-urgent digital stuff (export Evernote and transfer to new system!) to major work priorities (resolve edits on story running tomorrow!). So I created categories: Jobs, Musical Theater, Newsletter, Admin, Life Stuff, Chores. Your categories will look different, but when everything in a column ladders up to the same purpose, it’s easier to focus. You’ll stop worrying about a simple chore at 9 a.m. right before your morning meeting.
Creating categories can squelch the seduction of multitasking and establish more boundaries in your work and personal lives. Work stays at work (even if that’s still a corner of your living room) and home stays at home.
Bite off little bits
It’s important to investigate the language of your list and make sure each item is truly one discrete task, and not a handful smushed together. Yes, this will make the list look longer. But it will also make it easier to mentally digest.
Once you have your Monster List organized into categories, it’s time to look at your daily flow. Let’s say one of my big tasks was applying for graduate school. “Apply for grad school” is a terrible to-do because there are probably a dozen steps along the way. Do yourself the favor of breaking it down into achievable goals. Adding more small items to your to-do list doesn’t give you more work. In fact, it’s the opposite: It gets you closer to your dreams.
This way, when you’re faced with your to-do list every morning, you’re looking at bite-sized, doable tasks. You’re turning your moonshots into reality.
Revel in the impossibility
Keep an ongoing “impossible” list and you don’t have to start from scratch every day. You’ll be able to frequently cross off a handful of tasks each day. Progress! You’ll finally deal with some tasks that have lurked in the shadows for too long. And you’ll always have your moonshots in sight.