Is there such a thing as a sustainable todo system?

It was summer of 2006 and we had just moved to San Francisco, sans jobs. I spent the summer job-hunting and doing a little freelance work, but mostly hacking on some side projects. I felt tremendously busy, but looking back, it was mostly self-imposed busyness stemming from boredom and the restlessness that comes from not having a job for months. As the items on my todo list grew, I became more and more stressed out. Finally, in a moment of desperation, I picked up a copy of Getting Things Done by David Allen and started down a really interesting road.

Side note: for those of you that haven’t read the book, I highly recommend it, but this isn’t really a review. Even if you’re a time management ninja, there’s almost certainly some good stuff in the book that you’ll enjoy.

To boil the gist of GTD down into a single sentence: you must have a workable system for keeping track of your tasks and responsibilities that you always use, and thus grow to trust completely.

I have this picture forever fixed in my mind of laying in the grass under a tree in Union Square on a warm summer afternoon, reading the final chapters of GTD and being as stress-free as I could remember in a long time. Just implementing the simple things in the beginning of the book had already made a big difference.

Fast-forward to now, 4.5 years later. I still use GTD and I’ve been using Omnifocus to manage it for the last few years. But I’m increasingly frustrated with it; I don’t keep up with my weekly reviews, I don’t use the system consistently enough to trust it, and I’ve increasingly found myself reverting to paper or my whiteboard when I’m in crunch-time and really need to get stuff done.

My tendency is to assume that I’m just not disciplined enough and redouble my efforts to make the system work for me. But I’m starting to wonder if there’s something else I need to consider. I’ve talked to a lot of people who have skipped from todo system to todo system, getting an initial high of productivity and then moving on. Maybe that’s just how it has to be; perhaps our brains are wired such that we need to vary our routines and methodologies or we slack off over time.

Another possibility is that I’m simply trying to do too much in my life, and there’s too many details to manage in any system without some things falling through the cracks. And it’s not even active projects; I’m not great about being honest and marking tasks and projects as “Maybe/Someday” to indicate that they’re not really that important to me right now. As a result, I always have items in my task queue that I’m probably not going to do, when it comes down to it.

So I’m going to take three actions to hopefully improve the situation:

Re-read Getting Things Done

In spite of the fact that it’s not working great for me right now, GTD has definitely been the biggest productivity bump I’ve ever received, and I’ve often experienced that re-reading a book that had a big impact on me in the past can help me see the lessons in a new light. Hopefully another pass at the book after a few years of living the system will give me new insights and inspiration.

Clean out my Omnifocus

I want to drastically reduce the number of projects, next actions, flagged actions, and due actions on my list. This means aggressively deleting things I no longer intend to do, or putting things in the someday / maybe bucket if they’re not truly active projects. I’ll try to keep it to five active high-level projects [1] and only things that I intend to do this month. Anything else gets put into someday / maybe to be reviewed at a later date.

Actually do my weekly reviews

I haven’t come up with a really good way to ensure that I do this, but I do notice a dramatic difference in the effectiveness of my GTD system when I don’t do my weekly reviews. I’ll plan on doing these on Friday mornings at 8am, without exception.

If you have other tips that you’ve found useful, or you have a todo system that has worked for you consistently for years, I’d like to hear about it. I’m open to changing, but I need something that will help me manage a wide variety of knowledge management tasks without things slipping through the cracks. GTD has come closest, but let me know if you’ve got another contender.

1. In GTD, anything that requires more than 1 action is a project, so implementing a minor feature for a client that takes an hour might actually be a project, because it has multiple steps. When I say “high-level project”, I mean collections of GTD-projects around a related node, like building a web application for a client, or learning iOS.