Effective To Do Lists: A Comprehensive Guide

I have spent a lot of my free time over the last year researching personal growth, productivity, and organization systems in an effort to improve my workflow, as a fundamental component of my self-improvement quest. 

The number of “Top 10” lists that I’ve encountered alone would outnumber the sum total of shady members of Congress.

Doing this kind of research is also often a painful exercise because the advice is littered with one (or more) of the following flaws:

  • it’s incomplete,
  • it’s poorly written,
  • it’s poorly contextualized,
  • and frequently it’s just plain wrong!

For me, researching a topic as seemingly simple as writing an effective “to do list” ends up as a perpetual exercise, since I’m always coming across yet another list. In fact, I’ve been finding myself doing this sort of research more frequently than ever, as of late, because of my current productivity experiment. And, I think I’ve come to one major conclusion:

Lists Are Stupid

There, I said it. It’s out in the open, and that statement right there even makes my personal blog here look a little bad, since I too have more than a few of those ignoble “list posts.” But I’m done writing that kind of post, because while the terse, feel-good advice might have some value, the mode of delivery often thoroughly minimizes the true complexity of the issue.

My number one qualm with advice from strangers online — which is going to be awfully hypocritical of me given the content of this site — has to do with the one-size-fits-all nature that every productivity blog seems to fall into. 

 “You will be more productive if you do this, this, and that.” — Every Productivity Blogger, Ever.

Call me a hypocrite all you want, but from now on I’m going to do my best — and for this post especially — to deliver advice with an emphasis on the fact that I am guaranteed to tell you something that is wrong… for you.

I don’t know you. Well, I might, but I most likely don’t. (That might not be true either, given my readership). I cannot begin to offer you a comprehensive guide to making a great to do list without telling you that, at the end of the day, your list will absolutely be different from mine and what works for you won’t work for everyone. There is simply no one way to make a to do list correctly. There is no silver bullet list that’ll solve all of your productivity problems. And if your to do list or lists functions poorly, it’s your own damn fault for not figuring out how to fix it.

That said, while list posts online are arguably incredibly stupid, having lists as a part of your workflow is not. That’s the one universal productivity truism so fas as I’m concerned.

You have a limited mental capacity — and if you don’t, then you should definitely talk to me about dark energy — because you are human, so you cannot possibly effectively keep track of everything in your head.

Unless of course you are blessed with lots of money, no responsibilities, a hyper-organized significant other, or some combination thereof. But I’m broke, I have two kids, and I’m trying to start a brand-new career. (I’m also smart enough not to comment on the organization abilities of my wife. Love you sweetie!) I don’t have the luxury of inadequately keeping track of the things I need to do.

The single most effective method for dealing with the limited capability of the human brain to manage discrete information to store that information. Lists are effective for such storage. The are particularly well-suited to task management because they can store large quantities of small, discrete chunks of data. Those small reminders are typically all that one needs to access the more complete information about that job that is never really forgotten, but instead merely misplaced, by your brain.

In other words, I could write “backup” on a task list, and when I look at that single word two days later it’ll remind me that I wanted to re-schedule my automatic backups to run twice daily. Of course, that’s me personally, and if your brain can’t easily access that data later than your system can adapt. Maybe you need “backup schedule” written on the list to be an effective reminder. Maybe you boss would need to have the entire sentence written down.

My point, here, again: it all depends upon you!

So, now that I’ve highlighted why I think it’s bad to read advice on the internet, it’s time to get to the meat of this post… wherein I give advice on the internet.

Here’s the deal, this is your list, so throughout I’m not going to ever say that you need to do something one way or another. Instead, I’m just going to provide a large sample of ideas which you can try to see if they work for you. These are some of the very things that I’m trying out with March’s productivity experiment; where I go analog for a month.

With that said, you don’t even have to go that far to try out some (or all) of these tips. We are “tool neutral” here at kellenmurphy.com. I’ve used lots of tools in the past, and I never seem to find a single one that works perfectly, though some have come close in the past.

And now, without further ado, here’s my:
(Somewhat) Comprehensive Guide to Effective To Do Lists

Lists Work; Keep One (or More)

Pick a time to write your list each day, and build up the habit of always writing out what you need to do then. Good possible times are:

  • the night before, which allows you to get right to work the next morning, or
  • first thing every morning, which allows you to plan your day before you need to really get moving.

Consider keeping separate lists, classifying your work based on:

  • contexts (such as “Work”, “Home”, “At Computer”, “In Town”, etc.)
  • projects (such as “HST Data Paper”, “HST Tomography Paper”, “Thesis Ch. 2”, etc.)

Consider nontraditional lists, such as:

  • habits you’re trying to build,
  • a “To Don’t” list,
  • a “Thankful For / Gratitude” list, or
  • a “Win” list (to keep track of how awesome you are).

Use Tools That Work (For You)

There’s one big decision here: analog, digital, or a combination.

Going analog doesn’t necessarily mean you are a luddite. Pen and paper works great for a to do list because of the ease of adding information to the system. Just make sure you pick tools that you will actually use. Avoid a fancy notebook like a Moleskine if you have any reservations about crossing out mistakes, or getting the cover bent a little bit, or even (*gasp*) tearing out a page now and then. If you don’t use your list, you’re not really keeping one, you’re just carrying around a dead (but pretty!) weight in your pocket or bag.

Likewise, going digital doesn’t necessarily mean forgoing paper entirely; you don’t have to devote yourself to one tool if there’s no tool out there that works perfectly for you. In fact, I find it highly improbable that any product out there can serve your task/project management needs:

  • for every kind of project,
  • in every context,
  • at every hour,
  • for every energy level,
  • and every possible situation.

And going digital doesn’t necessarily mean committing to one app or piece of software, at all or even temporarily:

  • data can be exported,
  • everything has a free trial period these days,
  • what works for you now might not work for you next month,
  • and you can always use more than one tool for more than one purpose.

Use The Force List, Luke!

One of my biggest problems with sitting down to make a to do list is forgetting to return to the list to re-evaluate what I’m currently doing later on. To that end:

  •  check your list frequently,
  • don’t be afraid to add stuff to the list,
  • don’t be afraid to evaluate whether or not items on the list still belong on your to-do list:
  • things sometimes change,
  • tasks may need modification depending upon the outcome of other work,
  • consider have a “someday / maybe” list as a buffer for tasks you aren’t sure about anymore.

That said, it’s very important to not spend so much time working on your list, that you can’t actually do the things on the list. Strike a balance by forcing yourself to start working on something; your list won’t disappear, and you can always come back later.

And, along those same lines: don’t re-write your list every day. Doing so can increase task anxiety by realizing that you still have that big thing looming over you, yet again, and since anxiety and procrastination are intimately linked you might just find yourself in a vicious cycle. And try not to care if your paper list is messy, you’ll be done with it soon, and it’ll be just another piece of trash in the bin.

How It’s Organized (Doesn’t Matter)

Really, it just doesn’t. You can sort by projects, and sub-projects, and sub-sub-projects, and contexts within those, and then add sub-contexts; none of it matters if your organization is hard for you to use! The only right way is the way that works for you:

  •  Consider Prioritization (alphabetical, numeral, color, time),
  • Avoid “vague” tasks; those using verbs like “plan” or “think”. Instead, try to make every task use an action verb like “write”, “draft”, or “decide.”
  • Don’t make tasks too big: “write dissertation” is a really, really bad item for a to-do list. Trust me on that; I have first-hand experience there.

Try to make your tasks realistic and your work load reasonable; a task list with 84 items is not going to be knocked out in a single day, so while having a list that long might be a useful reference, a smaller to do list of 1-5 most important tasks/actions is probably better for getting things done on any given day. (Multiple lists really help here!)

Keep the lists as short as necessary, but no shorter: provide just the information/data you really need to know what the task is, otherwise you’re going to a) not pay close attention to what the task is, or b) overload yourself with spurious information whenever you glance at your to do list. Finding the perfect balance for you is difficult, will take time, but will pay off eventually.

Steer clear of terms like “start” for tasks, and instead focus on actions that give quantifiable results; starting is easy, focus on the finish.

It’s About You, Stupid

And, to conclude and to emphasize this point (again), it’s your to-do list. Not mine. Not your wife’s. Not your assistant’s. It’s yours; own it and take charge of your work. Remember, these are the things that you need to do to make progress on whatever goal it is that you’re working towards. If you succeed it’s you that will benefit the most. If you fail it’s you that’s going to hurt the most. Remember that, and consider adding that emotional context to your tasks, and you may find you’re more easily able to get started on your work.

Also, there’s no reason why you only have to put work on your to-do list. Consider “reward tasks” like “go for a walk” or “go get a coffee” to break up your day. Not only do you get a break, but you also get to check a job off your list, which will have the added benefit of making you feel more productive.

I’ll update this post in future as I think of / find more useful tips.