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I asked experts to analyze my to-do lists. This is what they found

I’d often start one project, only to realize that a more urgent one needed my attention. So I asked organizational experts to help give my to-do list strategy a makeover.

I asked experts to analyze my to-do lists. This is what they found
[Photo: Marten Bjork/Unsplash]
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As a solopreneur juggling multiple projects, clients, and income streams—copywriting, journalism, anthology editing, and event organizing—my to-do list feels never-ending. Make that my to-do lists, plural, because the gargantuan version I write each morning always morphs into up to a dozen smaller ones, some jotted by hand, some tapped into my phone or drafted via email.

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Keeping up with my to-do lists feels like a job in and of itself. Often my lists don’t seem to have any priority, with larger tasks like “learn Instagram stories” cozied up next to “call insurance company” or “draft interview questions.”

I felt like I could barely keep track of my multiple lists, meaning I’d often start one project, only to realize that a more urgent one needed my attention. I would set the first one aside, dive into the next, only to interrupt myself yet again. It felt overwhelming, and the lists, which I thought would help me get organized, were doing the opposite. I would randomly remember an urgent task that had somehow escaped the umpteenth iteration of a given list, sending me into a panic.

To help me sort them out, I decided to speak with organizational experts who regularly advise people on their to do-lists, to see if they could help me waste less time. I asked productivity consultant Rashelle Isip, author of How To Be More Organized Right Now, and Erik Fisher, host of the Beyond The To-Do List podcast, to analyze my to-do lists in all their messy, repetitive glory. I sent them a hand-written lined notebook sheet of a day’s to-do list, along with my smaller list for the same day that I created on my phone, and asked them to tell me how I could make them more constructive, as well as best practices for coming up with effective to-do lists and sticking with them.

Figure out the big picture

Before even tackling the nitty-gritty of my lists, Isip urged me to take a step back and ask myself what these tasks are helping me accomplish. After all, no one (hopefully) has lain on their deathbed bemoaning the fact that they didn’t cross off more items on their to-do lists. “Instead of just looking at the tasks for tasks’ sake, we have to recognize where the tasks are taking us,” says Isip. “Once you can take that longer view, then you can focus yourself on the tasks themselves.” In other words, knowing the broader purpose of your collective tasks can make even the challenging tasks easier to swallow.

Isip suggests monthly reviews to get your mind focused on what you have to do, personally and professionally that month, then break things down by goals for the week, before listing out your daily tasks. She also recommends a monthly, quarterly, or annual review of your past lists to see whether you’ve stayed on track with your goals.

Organize and maintain your lists

There are various approaches to organizing your to-do lists, whether by urgency, type of task (emails to send, calls to make, research), or project.

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Isip advised making an initial list at the start of each day of everything that’s in your head, then winnowing down that list and organizing it so you can see it more clearly. Separate the steps of bigger tasks, so you can see where you need to begin. For small tasks that take just a few minutes, it’s better to get them out of the way first, rather than waste time and mental energy writing them down.

Fisher warns that the key to any good to-do list is to keep it limited to that day’s tasks only. Fisher also recommends keeping a “someday list” for tasks where you don’t yet know how long they’ll take, their priority, deadline, or number of steps. “If it’s just something that comes up in your mind that needs to be done, but today is not that day, park it in the someday list and then trust that you will decide more about that item later at the appropriate time,” he said.

Both experts advised making sure your to-do list isn’t too big or you’ll not only feel overwhelmed, you won’t know how to prioritize it. “If you can pick the three biggest things that if you got those done completely today, you would call today a success at the end of the day, that day is a win,” said Fisher.

Pick a format that works for you

Fisher is an advocate of electronic to-do lists, since they can be easier to manage and update. He recommends them for prioritizing urgent tasks, which “may be done more easily with a digital tool that allows you to drag a higher priority item up to the top where it’s the next item.” With paper, you have to cross off and rewrite.

Isip believes this is a matter of personal preference. She recommends experimenting with different list formats and seeing which best suits your approach to work. “If you can’t stand one method, it’s not going to help you,” she warns. For those who want flexibility but prefer writing by hand, she recommends sticky notes that you can move around.

Isip said holding on to your lists (or storing them in an app which saves them for you) can help when it’s time for reviewing them, so you can see what you’ve actually gotten done versus what you hoped to accomplish in a given time period.

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In my sample lists I sent Isip and Fisher, I included business tasks as well as personal ones, such as calling my health insurance company. Fisher suggests keeping work and personal lists separate, so you can be more efficient when you’re on the job. “You can review the work list during work time and not get sucked into reviewing personal stuff then,” he says.

Isip says that the main goal when selecting a to-do list methodology is understanding how your brain works and creating a system that meshes with that. You may never have asked yourself whether you prefer a deadline verus unstructured work, or whether you prefer to send all your emails in a 30-minute block of time. Figuring that out can help guide your list making. “[You] know more than you think you know, you just haven’t necessarily tapped into it.”

I started using Isip’s method, making a new electronic list each morning for the day ahead, carrying over tasks from the day before, along with any I’d already scheduled for that day. This freed up a huge amount of time in my day, as well as giving me more mental space, because I wasn’t waking up each morning trying to start fresh, with the fear that I was forgetting something lurking. It also made the end of my workdays more peaceful. Rather than trying to cram work in at 9 or 10 p.m. (or later), I could simply shut down my computer, and my brain, at a more reasonable hour, knowing my list would essentially make itself the next morning.

Even though I find a deep satisfaction in physically crossing an item off of a paper list, using a digital method worked better, because I don’t always have a piece of paper handy. What was happening previously is that I would make extra notes on my phone to supplement the paper list, but I struggled to combine the two at the end of the day.

Since I always have my phone with me, I started using the app Evernote, creating separate notebooks for various long-term work projects and personal ones, and adding to the major tasks underneath them. Each day gets its own to-do list for me to make my way through, and I go through the project to-do lists weekly to make sure they’re on track.

The app makes it infinitely easier to find key information because it’s searchable, and means that instead of listing every person I have to call for a given article on that day’s to-do list, I can just write, “call sources,” knowing I’ve made a list of them in a designated notebook.

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Know which “dos” are actually “don’ts”

One of the hardest realities to face about to-do lists, for me, is that sometimes, even with my best intentions when putting a task on a list, it may just never get done, no matter how many times I write it down over many weeks or months. Isip says this is perfectly normal, and I shouldn’t feel guilty about not completing every single task. “That’s just the nature of to-do lists. Things will come in, some items will be processed, some items will fall off the list. It’s always a cycle.”

To help you figure out whether to let those tasks go for good, Isip urges you to ask yourself whether there was some sort of resistance or procrastination or was it simply a case of out of sight, out of mind? Maybe you’ve changed course in your career goals since you initially wrote down the task, or other, more urgent work has crossed your desk. If certain responsibilities are truly vital to your work or well-being, Isip says, “you’ll find a way to get them done.” So, if you haven’t, figuring out why can help you move past it—and get to the next item on your list.

This part of Isip’s instructions has been the toughest part of revamping my to-do list approach, with certain tasks that just feel overwhelming lingering on my list for months (including, ironically, finishing this article). I’ve started putting those at the top of my list and tackling them first thing in the morning, when I’m most alert. Usually, the tasks I’ve put off (and off and off) are not actually as daunting as they seemed. But I’ve also gotten better about simply removing some to-do list items that I’ve had to recognize I couldn’t finish, whether because I overcommitted, the timing was no longer right, or they simply weren’t a priority. I can always add them back at a later date if I’m so inclined, but not seeing them every day helps me focus on what’s most important.