Not a week goes by that I don't receive an email from some reader or listener asking about the problem of overwhelming task lists. Specifically, they explain that every day they spend far too much time dealing with an obese task list, for which they complete two or three items and fret over the rest. Then they spend hours fiddling most of their tasks into the next day only to start the vicious cycle again tomorrow. The whole process is demoralizing. Every morning feels like a quiet testament to your own personal failure. I know about this because I have experienced it. Not only does this wreck your faith in yourself, it makes you look like a flake to everyone else. You become the guy who says "yes" but never actually delivers.
Just because you can plan and track 10,000 tasks with your computer, doesn't mean you should. I know that sounds obvious, but at a certain level, it is not. We use powerful tools, like OmniFocus, that make the structuring and organization of our task lists a breeze. It is so easy to add another forty tasks each day. Why not?
The cure is a bucket of intellectual ice water. The first step is just awareness. Be conscious of the growing monster. If you routinely open OmniFocus to find yourself facing 200 tasks every morning, you're going to spend a lot more time organizing than actually doing. Don't fall into that trap. Instead, use the forecast mode and start dates to push tasks out until when you can reasonably accomplish them. Be aware that despite your best intentions, tomorrow will not be a 100 hour day. Some projects may need to go out several days, weeks, or months. (If you think a task needs to get delayed years, it actually needs to get deleted.) Start each day with a small manageable list and get to work.
Future planning, however, only goes so far. Some of your projects must die. You will find that even with smart future planning, the list is still too long. At that point, you're going to have to accept reality and start killing projects. This really isn't the loss you think it is. If you are overwhelmed with tasks, several of the projects on your list are already dead. Deep down, you already know you won't do them. You overcommitted yourself and it is time for the ice water. Be honest with yourself (and the world) and delete them outright rather than let them die a slow painful death, wrecking your faith in yourself (and other people's confidence in you) in the process. This step is empowering. It puts you in control of what you do and afterwards it feels great. Put on your big boy pants and start killing projects today.
Taking back control takes some time. Use as much time as it requires. It is worth it. Until OmniFocus 2 ships, I find it easiest to pull this off on the iPad, where you can use the forecast mode, start dates, and the delete project button to wrest control from the universe. If you are using a start date type planning method, you're still going to be hit with surprises over the next few weeks as previously delayed start dates show up. You'll have to be equally vicious with those where appropriate.
The payoff for this bloodletting is immediate. You will find every day that you have a much more manageable list of tasks and the quality of your work will improve. Moreover, that underlying sense of angst that comes with an impossible task list will go away and you'll feel a lot better about yourself.
You aren't out of the woods yet however. Taking on too much is not a habit easily broken. Even after you complete this purge, your task list will build up again. Constant vigilance! It is up to you to be on guard that you don't sink into the morass again. I'd like to say that I have mastered this skill. I have not. As I look at my own task list today, it's obvious I need to take out the machete once again.