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Building a Smarter To-Do List, Part II

Conclusion of our two-part series on improving the quality of your to-do list. Yesterday's post covered some basics and whys, the concept of the “next action,” and the importance of physicality.

« Start with yesterday's “Building a Smarter To-Do List, Part I”

Keep it Current

While you can and probably should track more than one next action at a time for each project (these are all the things that can be done now), it's vital to differentiate a true next action from any of the garden-variety items that just need to be done at some point later. In other words, be careful not to to turn your to-do list into an ad hoc project plan.

Now, now, now

Avoid the trap of littering your horizon with piles of crufty pseudo-tasks that can't actually be addressed (or, almost as often, can't be addressed yet). While you want to always stay aware of future obligations and the work that they are likely to generate, the to-do list is absolutely not the place to do it. Keep your to-do list a sacred tabernacle for current activity, and maintain longer-term task and support materials as well as appointments where they belong--in a project support folder and your calendar, respectively.

Remember: you should theoretically be able to choose any item from your list and, given the proper tools and context, start on the task immediately. Reveal hidden dependencies and move the later items someplace else; there’s no shame in tracking the small task that will keep things moving (and doing it is even better).

Trim, toss, and refactor

Make a habit of pruning your list of completed, dead, and obviated tasks. To be effective, your list should be alive-- a functional dashboard for understanding the immediate work at hand. And remember: your to-do list is not the place to park your ambitions or test the limits of your grasp. Constantly break tasks down and down to the most atomic work possible, and be ruthless about moving (or deleting) stuff that belongs someplace else.

Why Am I Doing This Task?

This is important. When compiling a list of all the stuff that's on your mind (and on your plate), it's crucial to unpack how each task you accept or assign to yourself will support your projects, your roles, and the goals you've set for yourself. Before adding a new item, reflect on the value that each chunk of work brings to your world.

  • Is this the best use of my time right now?
  • Am I the best person to do this task?
  • Is this something that must be done now? Why now?
  • What happens if I don't do this at all?

To illustrate the significance of these questions in the grand scheme of things , I'll borrow (and freely butcher) an image from developer Joel Spolsky. Try imagining your available time and resources as a wooden box--a fixed amount of space that can only contain so many cubic inches of “stuff.” You'll be filling that box with wooden blocks of varying sizes, each of which represents a separate task on your list. The bigger the block, the more time that task will take (and the more metaphorical space it will require in your box). Got it?

Let's say your notional box has 8 average-sized blocks in it right now, with a maximum occupancy of about 10 blocks. Now, let's imagine you're thinking of adding 5 big new blocks to the box. Well, you have some decisions to make now, don't you? Some of those blocks might fit easily into a team member's box (hello, delegation), while others might be reduced in size to fit the available space. But more often then not, you're going to have to do the painfully obvious and just free up some space--either by removing some old blocks or by forgoing the addition of new ones. Of course, it doesn't go without reiterating that the smaller the blocks (tasks) you choose to add, the more flexibility you have in adding and moving blocks; think about how (what becomes) that big IKEA bookcase arrives in that flat little carton.

Remember: for the sake of this visualization, making your task box any bigger is not an option, no more than you can add a few hours to your day or a couple weeks to your month. So the only variable in your control is what you decide to put in or take out--what tasks will you choose. The bottom line is that both those blocks and the box are ultimately your responsibility, so brace yourself for some hard decisions on where your priorities lie.

If it’s on your list, it’s a commitment

Try to keep this box image forefront in your mind whenever you're tempted (or compelled) to shovel more work into an already-teeming inbox. Look at each addition to your to-do list as a personal commitment to completing that action. Bear in mind that every minute you spend working on one task is necessarily a minute you cannot spend working on another. So ensure that your to-do list honors these reasonable limits and keeps you focused on the work that's most valuable to you.

This actually takes a surprising amount of discipline and requires making a kind of deal with yourself; no more treating your to-do list like the hope chest where you toss all the stuff you should be doing or might maybe be doing. The to-do list is a plan, and it’s a contract. If you’re not sure you want to do an item, take it off the list. If you can’t envision what doing the task will look like, off it goes. Jot and doodle someplace else.

Like so many of the things we talk about here, the to-do list is really a cipher, albeit an important one. As the artifact of your short-term planning, it becomes the developing Polaroid of your next few hours, days, or weeks. So, reframing your list as “the things I want to have done” helps set the proper state of mind; this is your life for the next little while, so don’t be skittish about taking it seriously enough that you can depend on it as the tactical plan for getting you where you want to be.

Solving common hang-ups

Getting good at this stuff is a process. Don’t expect to be an instant master of the to-do on your first try. To help you navigate some of the challenges that frequently await your to-do list, here’s some strategies for getting out in front.

Get a running start

Start off your day or your week by giving yourself several tiny tasks that can be accomplished in just a minute or two each. Aim low, and don't be embarrassed to make these really, really easy jobs. “Clean the keyboard,” “Empty the trash,” and “Add paper to the printer” might seem like pointless busy work, but ticking off several fast items in a row can often be the jolt you need to start tackling the bigger, scarier stuff.

Delegate actively

If you're tracking tasks that you've assigned to others or are waiting on work from someone else on your team, resist the urge to shift responsibility for ensuring their timely arrival. Give yourself tasks like “Call Alex for ETA on redesign sketch” or “Email Bob for latest revision of Chapter 3.” This active follow-up especially deserves a spot on your list when others are depending on your piece of that work to keep the project moving and on schedule. Even when the ball is in someone else's court for the moment, always give yourself timely reminders to ensure that it returns to your side of the net when it's expected and needed.

Cringe-bust your to-Do List

Ever notice how some items seem permanently stuck on your to-do list? Days, weeks, seasons may fly by and the same three or four hoary old tasks stare back at you, stroking their beards and cackling. Chances are you've stopped mentally processing these to-dos as tasks in the world and now just let your eyes fly past them so as to minimize the guilt, pain, and cringing that they cause you.

You can “cringe-bust” your to-do list by printing out a complete set of current tasks--preferably in alphabetical rather than priority or project order. Run through the list quickly, placing a check mark next to any item that causes you the slightest anxiety or concern. The idea is to root out the items that you dread doing.

On your second pass-through of the list, make a note on a separate piece of paper highlighting why you've been avoiding each task. Is it fear of failure? Boredom? Garden-variety anxiety about the outcome? Whatever your reason--and do be honest with yourself--generate a new to-do for each item that addresses the “cringe” rather than the actual to-do that's causing it.

For example, if you're dreading calling an introverted customer because there's always weird silences in the conversation, give yourself a to-do to generate a few topics that you can bring up when things start to slow down. It won't make the call fun, but it will get you past the anxiety that's holding you up. The trick, in any case, is to deflate the cringe-y task by replacing it with a more active, manageable, and unintimidating one that drains the situation of the power to control you.

When you've succeeded, cross out both tasks with a thick red marker, and give yourself a high five. You rule.

Related stuff

What's the secret to your to-do list? What tricks do you use to keep it together and make sure everything gets done?

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About Merlin

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Merlin Mann is an independent writer, speaker, and broadcaster. He’s best known for being the guy who created the website you’re reading right now. He lives in San Francisco, does lots of public speaking, and helps make cool things like You Look Nice Today, Back to Work, and Kung Fu Grippe. Also? He’s writing this book, he lives with this face, he suffers from this hair, he answers these questions, and he’s had this life. So far.

Merlin’s favorite thing he’s written in the past few years is an essay entitled, “Cranking.”




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