I have a huge task list. This isn’t necessarily a bad thing, since the list is well-organized and useful (see “Why Organization Improves Motivation, and Some Organization Tips“), and a lot of the tasks on it are a handy but optional. I do my best to push items that are important and need to be done soon to categories and statuses that keep me focused on those (see “My Top 1 Task“), which seems to work pretty well for me.

Still, the sheer number of items sometimes gets to me. To clear up a lot of them at once, I apply a version of the 2-minute rule, learned from David Allen (see “Useful Book: Getting Things Done“). The two minute rule is If you can get something done in 2 minutes, don’t put it on your task list: instead, just do it.

Part of the logic behind this idea is that keeping an item on your task list requires time and attention from you: you need to review your task list periodically, keep items prioritized, and so on. With a good organizational sytem (like Allen’s), this isn’t difficult, but it becomes easier the fewer items you have to manage. So tasks that can be completed in 2 minutes tend to “pay for themselves” if you do them up front rather than spending the time writing them down maintaining them until some point in the future.

Two minutes doesn’t sound like much, but there are a lot of useful things that can be done in that time, including firing off a reminder e-mail, making a telephone call to check a single fact, finding an item or paper that isn’t too hard to locate, asking someone one question, and so on.

And it doesn’t have to be a 2 minute limit, as long as it’s a short period of time: it could be 5 minutes or even 15 minutes, though probably not longer than that.

To use the 2-minute rule on items that have already made their way onto your list (for instance, because you added them before you heard of the 2-minute rule, or because it wasn’t possible to do them at the times you first thought of them), you can either get in the habit of searching for 2-minute items whenever you have a few minutes free, or better yet, go through your task list and mark any 2-minute items you already have. In my case, I have two separate tags I use: “5 minutes or less” and “15 minutes or less.” You can then jump to a quick-to-do item whenever time allows, or block out an hour or two and mow down dozens of them.

And interestingly, marking quick tasks in your task list, if it’s done in an efficient task management system (like ToDoist or a paper system)  only takes a few minutes.

Photo by Јerry

I heard recently from Debra Exner, who does coaching and training work about effectiveness and collaboration, and thought I’d take a look at her Web site, CollaborationPaysOff.com. I immediately found some very useful material, for instance in a new series of posts on the site called “Get Things Done: 4 Ways to Collaborate for Accountability,” which includes strategies like “Get-It-Done Days” for organizational work, during which participants check in with each other every hour to report progress and state goals for the coming our; and “Mastermind Groups” of individuals who get together to talk about their individual goals, their progress, and their concerns so that the whole group can provide accountability and brainstorming.

If you’re interested in organization, collaboration, productivity, or creativity, I’d recommend taking a look at the site and perhaps subscribing to posts by e-mail to let Debra and site co-author Maddie Hunter provide some useful ideas.

I love organization. Seriously. Not in an OCD, “wait, wait, that doesn’t go there!” kind of way (I think my girlfriend is laughing at this point, but let’s please disregard that), but in a “wow, now I don’t have to spend time worrying about all that crap because I’m taking care of it!” kind of way. I love looking at an empty inbox: see “How I’m Keeping My E-mail Inbox Empty“–more than a year later, this is still working as originally planned. I love to check Todoist, my preferred freebie task management system, and realizing that I’ve actually done everything necessary to keep the world from exploding for the next little while.

Yet organization gets away from me, and my problem is simply losing confidence in my system.

How to undermine an organizational system
For instance, I’ll look at my inbox, and there will be several things I would like to respond to soon. Sometimes I succumb to temptation and leave those things in my inbox, since “surely I’ll get to them soon.” Sometimes I even do get to some of them soon, and off they go into my “already read” folder or the trash bin. Other times, though–many, many other times–I won’t get to them soon, and they will linger in my inbox until I get real, actually take the steps, and put them where it really goes (often in my “Reply/Act” folder, while other times an item may need to be briefly read and then added to my Todoist task list).

Similarly, sometimes in Todoist I’ll let several things pile up in my Top 1 category, and before I know it I’ll have a list that stretches off the page–and “Top 1” is the place I’m supposed to be able to look to know exactly what I need to do next!

Confidence making confidence possible
The problem with “yeah, but”ing my organizational systems isn’t just that it holds up dealing with the items I’m not handling properly: it’s that it chokes up the whole system. If I’m preoccupied with trying to decide on which, if any, of the dozen e-mails in my inbox to respond to, then that means I’m not paying proper attention to my “Reply/Act” folder or periodically reviewing my Pending folder, and at that point the whole thing falls down. Only when everything gets sorted into its rightful place does the system really work again.

To put it another way, if I don’t continually show complete confidence in my organizational systems by following them even if I’m worried about one particular item or another, this will tend to undermine the whole system and make it fail. It’s natural to worry about individual things getting lost in an organizational system, since we focus on one thing at a time and tend to minimize the importance of other things while we’re doing it, and since most of us have a lot of experience with failed organization systems in the past, even if our present systems are working beautifully. Yet there’s still no reason to jump ship and land back in the Sea of Chaos.

Taking the steps
None of the complications of not sticking to an organizational system should surprise me. After all, in my post “Why Task Lists Fail,” I specifically point out how not prioritizing (that is, not sticking with a clear and effective organizational system) is the kiss of death to a task list.

In asking myself “Are you taking the steps?” recently I was immediately forced to confront this situation. I did a little triage on my task list and the one inbox (out of two) that wasn’t already cleared out, and literally within a few minutes, I was back on track. This doesn’t mean that I was caught up on everything I needed to do, only that I had my ducks in a row after that so that I would know what that next thing was. If I don’t know what specific thing to do next, how can I get that thing done?

Photo by iBjorn

“Overwhelmed” isn’t a very good state of mind in which to make decisions. When we have too many things competing for our attention at the same time, it becomes difficult or impossible to compare them all to one another at the same time. It’s like having a whole classroom of kids calling out answers, or a dozen different messages coming up at once on the computer: if there’s no time to stop and go through the items one by one, we may be able to pick out useful things here and there, but we can’t evaluate all the choices effectively. At this point, habit tends to take over. If the habit in question is a good one, that’s great, but in areas where we’re trying to make life changes, this is generally bad news.

The way to make better choices in these situations is to narrow things down, to get the choices to a small enough number that we can make an intelligent, considered decision about which to pick. Two good ways to do this are sequencing and filtering.

Filtering: honing in
If you know certain things about the choice you want to make–for instance, that you want the job applicant to have sales experience, or that you want to pick a menu item that’s heart healthy–you can filter by putting aside or ignoring all the options that don’t have the quality you’re looking for. Once you’ve done that, you can filter or sequence further to get an even smaller set of options, or if the group is small enough, choose directly from the filtered selections.

The reason filtering is often better than evaluating items one by one is that it’s easy to get distracted or preoccupied with less-important factors when you have a lot of different criteria to consider. Going through options one by one, you might end up hiring someone with a really good cover letter but no sales experience, or eating the delicious-looking fried food platter that caught your eye.

When to use filtering
Filtering is mainly useful for situations when you have specific, definite needs. If sales experience isn’t essential, for instance, then filtering by it could make you ignore the best candidate for the job. In cases where you can’t come up with rules to apply to narrow down selections, sequencing may be a better choice than filtering.

The exceptions are for less-important decisions or decisions you have to make very quickly. If you want to make a good decision but don’t necessarily have the time to make the best possible decision, or if the time involved in considering every possible option isn’t worth it for the decision you’re making, then filtering is still useful even with criteria that aren’t entirely absolute.

Sequencing: one thing at a time
Sequencing means taking the options one after the other and considering each of them. You can consider each item individually and pick out only your top choices, or compare each item to the item after it and choose between each pair. With the first approach, you should end up with a much smaller set of options that you can either consider as a group or sequence or filter to narrow down more. With the second approach, you’ll already have your final choice when you’re done going through the list.

Sequencing is also very useful when you have a set of choices that aren’t numerous enough to be overwhelming, but that are difficult to choose from. Comparing each item to the next and carrying along the “winner” of each comparison makes it possible to focus attention on just the differences between two choices.

Whether you use filtering or sequencing, narrowing down choices is a good defense against feeling overwhelmed by options, and a good way to serve your goals rather than serving the habits you’re trying to break.

Photo by ZeHawk

Over the past few weeks I’ve been through a major effort to go through all of my earthly possessions and get rid of everything I really don’t want or need. I used the “In what kind of realistic situation would I actually want to pull this out and do something with it?” test to decide what needed to go, as mentioned in my recent article “Some Tips for Getting Rid of Things.”

The things I set aside to get rid of went to a variety of places, some like the ones I mention in my article  “Clearing Your Mind by Cashing In.” Many items went to ReSource, a terrific local non-profit that provides a household good reuse store, building materials reuse store, and other departments while creating jobs and teaching job skills. Other materials were sold through Craigslist, given away through Craigslist and Freecycle, and set aside to be sold on Amazon and eBay. Of course our trash cans and recycle bin were also given a thorough workout.

The process, which is still in progress for me (I still need to finish going through books, primarily), took much longer than I would have imagined–but it also yielded a lot more things to sell or give away and freed up a lot more space than I would have imagined. Best of all, it has been taking innumerable little pressures and worries away: things I’ve held onto to fix or reuse somehow that I finally realized were trash, projects of going through things that are now done, and so on. Physical clutter can create mental clutter.

Coming to the end of this big push, I now have to ask myself: would it have been a lot easier on me to do this little by little over time? Or did I need to do it in one big push to do it at all?

The big push approach
The big push has some significant up sides. One of the biggest is that I didn’t have to reorient and remind myself of what I was doing every time I restart, which meant I could work efficiently. Another is that I could attack one part of the house, pull out everything in it, and take over as much space as I needed until I had sorted through all of that material. I also was able to easily keep focus on the job once I had started.

Yet another thing I like about the big push is the sense of accomplishment and catharsis. The change in my house was drastic, fast, and visible.

When doing a big push, it’s generally necessary to plan in advance and carve out time during which not only do you not have your usual responsibilities to attend to, but you won’t be badly distracted by other things you could do with the time, like socializing or relaxing. Big pushes generally require clearing the schedule, locking the door, and unplugging the phone.

The little by little approach
As great as the big push is, little by little has one killer advantage, which is that big pushes have a bad habit of never happening. For instance, if I were to wait until I actually had time to go through every piece of paper I own to get my papers organized, there’s a good chance that would literally never happen. Going through my things has taken about five full days so far–and I do mean full!–and that’s not counting the time I still need to put in selling off some of the things I’ve identified to get rid of. Being able to take that amount of time for organization alone was a rare opportunity, one that I jumped at, and for me, such opportunities come along often.

Another advantage of the little by little approach–and this too is a major plus–is that doing something consistently makes it into a habit. This is very useful for things that we’ll need to keep up once we get to our goal state. For example, if I were to do a major landscaping effort on my yard, doing it little by little would get me in the habit of working on the yard, which would be important to keeping up everything I had done in the initial effort.

Deciding on which approach to use
So if you’re facing a monumental project and are trying to decide whether to crank it out all at once or to do it little by little, here are some questions to ask yourself and some ideas to guide you based on those answers.

• Does it need to be done at all? Even though the project may be a worthy one, are you willing and able to devote the time it will require? For instance, it might be nice to send Christmas cards to 200 people this year, but is that project high enough in your priorities to be worth the time it will take?
• Does it need to be done very soon? If so, you may have no choice other than a big push.
• Is efficiency of the essence? Big pushes tend to be more efficient than going little by little because of not having to stop and restart.
• Are you going to learn as you go? When doing something little by little, you have a chance to reflect on and refine your methods. This can lead to great improvements in how you handle your project.
• Can you free up the amount of time a big push will need? If not, little by little is your only option.
• Will this be something you’ll need to maintain once the initial work is done? If so, little by little can do a better job of helping you develop the habits you’ll need.
• What if the project goes over? For most large projects, estimates are more guesswork than reliable prediction. If you were to set aside an amount of time for a big push and at the end find you needed twice as much time, what would you do? On the other hand, if you were going little by little and found out the project would take twice as long as you thought, would that push completion too far away into the future?
• Will you be getting help? Some help is better suited to big pushes, as with decluttering or physical labor. Other help is better suited to a little by little approach, as with processing documents that arrive through e-mail or working with people who don’t have large chunks of time available.

Whatever your approach, connecting with why you want to do the project will help you remain motivated.

Photo by druid labs

I’m currently in the midst of a two-day “decluttering vacation,” taking time off from my regular work to go through my house, get rid of things I don’t need, and organize the things I have left. I used to live in a larger house with a fair amount of storage, and I also used to have a less realistic idea of what I might really, actually use some day, so even though I’ve been getting rid of some stuff in recent years, my current, smaller house, which doesn’t have much storage space, has some packed closets and corners that I’d really like to clear out. (See my article “Clearing Your Mind by Cashing In.”)

It seems to me that the hardest part of decluttering doesn’t have anything to do with time, space, or materials: it’s the decisions. You find a book you read and liked ten years ago, or a tool that you’d lost for two years, or a stack of letters from a friend, and you think “Should I get rid of this? Will somebody be insulted if I get rid of it? Where would it even go if I did get rid of it? What if I get rid of it and I need it? I paid a lot of money for this!” and so on.

Many of these questions are misleading, because they get us involved in a lot of drama over the objects that doesn’t help us figure out whether or not the object belongs in our lives.

Let’s first say that if we don’t have any use for something, it’s best to get rid of it, even if that takes time and effort. I had a large laptop battery that was tapped out, no longer usable–but I didn’t want to throw it away, because I knew some of its materials might be toxic and that it could be recycled. I walked all over downtown Montpelier, Vermont trying to find a suitable battery drop-off, then did some searching online, then finally took it to a recycling bin for batteries at a local Best Buy store (though I also could have taken it to the dump and put it in the right place there, it turns out). This was a pain in the neck, but it was less of a pain in the neck than holding onto that useless object for the rest of my life! And the feeling of accomplishment and relief, although small, made a truly positive impact on my day.

So for the moment disregarding the question of what is to be done with an object once we decide it needs to go, here’s a proposal for a question that can help decide whether or not it should go in the first place: “In what kind of realistic situation would I actually want to pull this out and do something with it?”

Keep in mind that we’re trying to picture a situation that would actually happen, in which we would know where this item was, be willing and able to find it and get it out, and experience happiness or relief at having it available. There has to be a plausible payoff to keeping the thing. If there is no payoff, no value to keeping it, then it’s probably worth letting go.

It can take some time to get past our gut-level panic reactions at tossing something we may have had for years or paid a bundle for, but the effect of successfully ditching objects we really don’t need is often one of relief and pride, not to mention better organization and increased closet space. While getting rid of stuff isn’t always the most useful thing to do with our time, when it does come time to face that task, it’s an opportunity for becoming happier and more free.

It also can be done–and often will be more rewarding when done–in small amounts every day or several times a week rather than in one big push. (See “How to Reduce Stress and Get More Done by Turning a Project into a Habit.”)

One last note: decluttering doesn’t apply to data in the same way it does to physical objects. Electronic information can be searched automatically and takes virtually no physical space, and the amount of storage we have for that information grows exponentially over time as technology improves. So spending a full day going through all the files on your computer and deleting the ones you don’t need is probably not a great use of time. This is not to say it’s never worth deleting or offloading things from your computer, only that organizing data doesn’t pay off in the same way organizing objects does.

Photo by sindesign

This is the third article in a short series on prioritizing. The first article in the series, “Principles for Prioritizing, Part I: Moving Targets,” includes links to other articles on the site about organizing and prioritizing and is followed by “Principles for Prioritizing, Part II: Unimportant Tasks.”

3. How important something feels isn’t always a good indication of how important it is
To gauge how important something really is, it helps to put it in the context of what you really want in life. What are your key priorities? Going by gut feeling can sometimes lead us in the wrong direction because a task may be appealing or exciting or seem important because we’re wrapped up in it, when in fact it isn’t as important as other, less dramatic tasks. Try to judge the importance of an item from a distance, when you’re not deeply wrapped up in the task itself, by thinking about what effect it is likely to have in your life.

To get out of an obsession with a particular task that isn’t really a priority, allow your attention to focus on something else for at least a few minutes: have a conversation with a friend about a subject of mutual interest, or do a small task that’s unrelated to the one you’ve been involved in. These few minutes allow your brain to reorganize so that it’s not focused on that one possibly unimportant task, and let your physiology reset so that you’re not swept up in the biochemical side of emotion. In this state of mind, you can consider that appealing task in the context of all your other priorities.

4. The most important goal of prioritization is to find your top few tasks–especially your top one task
If you have a 200-item task list, it’s not particularly important to get all of your items prioritized so that, for instance, items 183 and 184 are in the proper order. Realistically, you may never get to items 183 and 184, and even if you do, circumstances are likely to change by the time you get there. The most effective way to prioritize is to care just about the top few tasks for the moment, so that you know what to start doing immediately and have one or two things queued up after you finish that first item. Doing this allows you to do what a task list is meant to help you do: focus on the one thing that it would benefit you most to be doing right now.

Finding those top few tasks may mean skimming over all 200 (or 20, or 2,000) items in your task list, but when skimming, the only thing to be thinking about is “what here would it be really good for me to tackle very soon?” The tasks that meet this criterion can then be sorted through with the question “Which of these would be most beneficial to do right now?”

That list of “very soon” things should never be more than a half dozen items long unless they’re very small items if you want to make good use of your searching. Anything more than that, and priorities are likely to change before you get to all of the items. Prioritize for the moment.

Photo by Chris JL

This is the second article in a short series on prioritizing. The first article in the series, “Principles for Prioritizing, Part I: Moving Targets,” appeared Monday, and includes links to other articles on the site about organizing and prioritizing.

Less important tasks may need to be dropped
When prioritizing tasks, we’re always dealing with at least two variables: how important something is and when it needs to be done. Do we do the immediate, less important thing or start working on the longer-term, more important thing instead? There’s no easy answer to this, but there are some ways to figure it out.

Of course important tasks that need to be done soon should take priority, and unimportant tasks that aren’t needed right away should be bumped to the end of your list–which for many of us may mean (sadly) that there will be no time for them. But of those other two possibilities–more important but less pressing and less important but more pressing–the decisions become more difficult. If you find that you are generally getting important things done on time without your life going haywire at all, you can probably afford to do the more urgent but less important tasks some of the time. But if you find that important, long-term things are often not getting done, not getting done well, or not getting done until the last minute, then what generally needs to happen is for some of those short-term but less important items to be dropped entirely from your task list so that you can get the more important things done.

For example, if you have a choice of working on some tax paperwork that’s due next week and reading a book for your book club meeting tomorrow, and if you find you often have trouble getting things like that tax paperwork done on time, then it’s probably time to take a hiatus from the book club.

To put it another way: effective prioritization often means giving up on less important tasks.

Photo by gingerpig2000

One of the most challenging things about managing a task list is prioritizing. You may literally have hundreds of things to do, from raking the leaves to learning a new job skill to making up a will. Comparing and ordering these items can be overwhelming.

Following are some basic principles to apply when prioritizing tasks that can help make sense out of a very complex set of priorities.

1. Priorities change all the time
It would be nice to be able to assign every task a priority that never changes, but from day to day–and sometimes hour to hour–too many things change for this to be the case. Scheduling a check-up becomes gradually more urgent the longer we put it off, or suddenly more urgent if health problems come up. Projects around the house may have to slide down the list of priorities when a new obligation comes up that makes it unlikely there will be time for them. Problems solve themselves or get worse from inattention; opportunities arise; people change their preferences and actions. Therefore, the best prioritization we can really achieve is the priority of things at the given moment, and the most effective task list is one that you can (and do) regularly re-prioritize.

This series will continue over the next several posts.

Related articles that may be of interest include:

• How Exceptions Cripple Organization
• 6 Steps to Overcome Procrastination
• My Top 1 Task
• Getting Rid of the Little, Distracting Tasks
• Useful Book: Getting Things Done
• Why Task Lists Fail
• 4 Ways to Make Sure You Get a Task Done
• Relieving Stress by Understanding Your Inputs
• To Free Your Mind, Capture Your Responsibilities
• Why Organization Improves Motivation, and Some Organization Tips

Photo by nerovivo

There’s a common, natural tendency many of us have to think of a thing as more important if our attention is focused on it. This can both help and hurt us. The helpful thing is that this can offer an easy way to get started on a task, because the more we think about something, the more likely we are to do actually do it.

Where this instinct hurts us, though, is in situations where we don’t organize a piece of information because we’re worried about losing track of it.

The problem is that to keep on top of a variety of incoming information, we need to handle all of it, pretty much without exception, using the same system. For instance, if we’re using a Getting Things Done approach to organization and an important letter comes in, Getting Things Done tells us to process it immediately or put it in our inbox. But we may hold back, thinking “No, I have to be sure to remember to do this! I’d better prop it up in front of my computer instead.”

Or if using a clean inbox approach, we might get a long e-mail from a friend who’s been out of touch for some time and think “Oh, I’d better not file that in my Reply/Act box, because I don’t want to forget to write back as soon as I can.”

Unfortunately, continuing to do this leads to pieces of paper lying around all over the place or e-mails stacking up in the inbox, each one of which distracts us from our organizational system and is hard to keep track of on its own. It’s too easy to not trust an organizational system and to try to make exceptions for whatever’s right in front of our eyes. When we do this, the organizational system rapidly collapses, because organizational systems that aren’t used to handle pretty much everything aren’t much use.

If a task or message can be handled right away, though, the situation is a bit different: responding to something immediately may bypass priorities (for instance, you might spend a lot of time on the reply to that friend when it’s more pressing to follow up on a medical issue), but something will get done. The most serious problems come when something that can’t be dealt with right away is held out for special handling.

The essence of an organizational system, or at least of the kind of organizational systems I can recommend as being truly effective, is using it for everything and faithfully reviewing everything in your system often enough that you never lose track of anything that goes in. It requires a leap of faith as well as a change of habit–and so it’s no wonder that it takes some effort to make the transition from organized to disorganized. But when that transition happens, our efforts are richly rewarded not just by improving our productivity, but also by transforming scattered, anxious feelings into a measure of confidence and serenity.

Photo by nickwheeleroz