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Is there such a thing as a sustainable todo system?


Posted in Goals, Inspiration, Personal, Posts by

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.

You might also enjoy:

  1. Project Goalpost
  2. Update on 21times
  3. How I use Omnifocus to get things done
  4. 21times startup sprint wrap-up
  5. Why productivity is cyclical and how to deal with it

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24 Responses to “Is there such a thing as a sustainable todo system?”

  1. BostonOU says:

    I'm just now finishing GTD and started using OmniFocus as well. Your 2006 is my 2010; I'm quitting my job and going full-time freelance while moving to a new city and trying to sell my house. Needless to say I've had a lot to do but GTD has really been amazing. I'm going to reread it because I pretty much flew through it so I could pick up the basics.

    Do you use GTD/Omnifocus for managing your development as well? It doesn't seem like it'd be great for managing all of the project details. Seems great from a high level perspective though.

    Also, why'd you choose Friday morning? Why not Monday morning as a start to your week?

  2. One thing that helped me to reinvigorate my GTD use was to listen to David Allens on tape. I got these MP3's of a class he did one. It's pretty long, maybe 8 hours worth but he goes through the entire book in a classroom setting. It's the same material but delivered differently and was a fantastic way to get back into the swing of things..

  3. @jaredtblake says:

    Another tool you might want to consider is Todo from Appigo (http://todo.appigo.com). They have both an iPhone and iPad version and just released a sync service with a web front end (full disclosure-I am part of the team that developed that in partnership with Appigo). We have spent countless hours studying GTD in order to develop tools that make the process easy for people to adopt and stick with.

  4. jordan says:

    I read GTD and have tried many Todo systems, most recently Things. I liked Things but I didn't realize until I started using Uncluttered Todo iPhone App that with Things I spent a lot of time managing the list instead of getting things done. The only thing Uncluttered didn't have was Mac syncing, which I don't need often, but is good to have. The developer let me know a free Mac client is on the way. My trick for staying with the program is to reserve two days a week for non-todos, for example, Sundays and Wednesday, I do whatever I want do whether it's on the list or not. Then rest of the time Im knocking things off of the list. Taking a break makes me infinitely more productive. Taking a break psychologically, makes you pay more attention to the list when you get back to it, without the burnout.

  5. @yesthattom says:

    You could try a lighter-weight system like the one in O'Reilly's Time Management for System Administrators. :-)

  6. jeff says:

    emacs org-mode is the best thing since emacs perhaps. although i am moving to using to using vim as my main editor i still use org mode for planning.

    • Michael says:

      +1 for that. I love org-mode, and stared (ab)using it for many other tasks. Some people even use it to create presentations with org-mode and the Latex beamer class. And thanks to MobileOrg it's even possible to sync your .org files to iOS devices.

  7. @alan_zimm says:

    For another view see "Work Less, Achieve More" by Fergus O'Connell. Basically says throw away most items on your list

  8. You should try using http://www.symphonical.com for your todos, it's mainly a tool for brainstorming, but you can easly manage your todos in a more visual way. I have no problems managing my tasks atleast :)

  9. I've only ever really been happy with a single Todo system, which I used for a year at my first job out of grad school. It was a notebook. Every morning when I came in, I would write each task that hadn't been done the day before as an item that needed to be done today. Any new bugs, tasks, etc., got a new line. Each item started with a dash next to it – . As I finished tasks, I would put an x through it, making an * . Before starting work in the morning, I would also prioritize my top-3 tasks by writing a 1,2,3 in the margin to the left of the -/* column.

    As a fairly goal-oriented person, putting an x through an item was very satisfying. And for those items that I didn't want to do, eventually I'd get tired of re-writing them every day, and I'd just sit down and get it done after my priority items.

    I used a standard spiral-bound notebook (with a pen in the spiral for meetings), and only ever wrote tasks on the right page, leaving the back-sides of the pages for design notes, algorithm ideas, and checklists. After leaving that job for Google, I'd planned on continuing that behavior, but Google gave me a laptop and I fell off the task/todo wagon (except when I was working on something that wasn't tracked in the bug tracker).

    Now, most of my tasks for work revolve around tickets in a bug tracker. Heck, I create bugs in the tracker to keep track of my personal progress in various branches (we use Git at my current position), whether they are requests from Product or not (it helps that if a ticket isn't filed, code isn't reviewed, and code isn't merged into production).

    I'd love to go back to a notebook for everything again, but I hate syncing between the notebook and a bug tracker.

  10. Steve Cooper says:

    Maybe running a todo list all the time just isn't that important.

    I tend to pick up a system like GTD when I'm starting to feel overwhelmed. I get everything down, power through a mass of the tasks that are stressing me, and then drop the system. Stuff gets done and my stress levels go down.

    GTD doesn't let you forget. Crappy little things that should just be deleted sit there accusingly. Every impulse becomes a project, every project demands action. I find if there's nothing burning on my todo list, it's time to drop todos.

  11. @bijanbwb says:

    Great post. I've been struggling with this same issue for the last few weeks. I've read and re-read GTD a few times and one thing that helped was to start underlining key parts and taking notes in the margin so that the next time I can just skim through it to re-apply it to my system.

    But I can certainly sympathise with you. I feel like I've used just about every "project management" tool and methodology out there by now. Perhaps the worst part is that they are all great. Things is a great iPhone app. Rememberthemilk has a great web interface. And other web services like ActionMethod and Basecamp are fantastic. Nonetheless, I experience the same periods you mention of hyper-productivity and the inevitable dips.

    Lately I've been thinking that there must be something missing that would keep us engaged in our productivity systems:

    For one thing, I used to throw out any to-do items once they were done, but I'm starting to think that holding on to completed tasks is important so you can come back and do some data mining to figure out what has been working and what hasn't been working.

    Secondly, there might be some sort of rewards or incentives that can be incorporated into the system to keep it engaging and make incremental progress more visible. I've used the EpicWin iPhone app and it's really interesting to see the idea of game theory applied to your to-do list in real life.

    I'd love to see all this come together (project management + self-tracking + game theory). But this just brings us back to the original question: how do you keep your system simple and engaging enough to keep it sustainable?

  12. Martin Kretz says:

    I think ZTD (http://zenhabits.net/zen-to-done-ztd-the-ultimate-simple-productivity-system/) is a great adaptation of GTD. The project/subproject/task-thing was always what tripped my GTD system up.

    ZTD helped me realize how important prioritization of tasks are, and how easy it can be implemented, and how they connect to setting a larger monthly or yearly goal. Settings a clear goal helps getting the focus right, and makes prioritization easier.

  13. jaderobbins says:

    My friends and I found we the same problem with commitment to task tracking systems. Being frustrated about it, we developed AgileTask <a href="http://(https://agiletask.me/)” target=”_blank”>(https://agiletask.me/) where you follow an agile software development approach to your task tracking.

    So in agile you decide and work on only what you can get done in a particular iteration, and keep a prioritized backlog of items that you can do when you are done with this iteration. In AgileTask we break up your tasks into "Today" and "Icebox", reflecting on what you need to work about now and what you don't need to be worrying about.

    We also use hash tags to allow our users to create their own organizational system (such as #project-name or #at-home) as well as achievements for working with the system to keep it fun and exciting.

    We would love anyone's thoughts or suggestions! Especially if it helps you keep productive :D

  14. Mark Sanborn says:

    You are totally right, I have bounced around a lot and skipping the weekly review almost always ends badly.

    You could try my app: http://agiletask.me which is super light weight, has an API, and you get achievements for getting things done.

  15. Joel N says:

    So ironic that this was your post yesterday as Jeanne & I just had a big talk about this last night where I confessed that for the past 3 years or so, I don't really feel like I've ever gotten a grasp on managing my various To-Do's, including work & personal, and have always felt like I could be way more effective if I implemented a system that worked for me. Oddly enough, you came up in the conversation as someone who seems to do a really good job of staying on top of the things that you need to get done, so I'd love to chat with you more about all of this sometime as I could definitely use some help! I started reading GTD about a year ago but then never ended up finishing for whatever reason (maybe because I rarely read :-) . Anyway, I think I'll give it another whirl and maybe we can discuss it together. Would love to learn more about OmniFocus as well. Thanks for sharing.

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  17. nathan t. says:

    I also go for the physical notebook and pencil method. Another thing that has really helped me (advice from The Ultimate Sales Machine) is to only put 6 things per day on your daily to do list, and make sure they are things that are possible to accomplish on that day. There is something really positive psychologically about checking all 6 things off of your list in the day vs. getting through 5 out of 20 actions…

  18. Good post, Ryan. Something that's helped me with weekly reviews – I'm pretty liberal about what a "week" is. If there's a five day block that seems like its own week, I do a review of the last five days. Sometimes I do a review of the last 10 days, or 14 days, or whatever. Basically, I review all blocks of time. Then for numbers like money spent, I divide by the days reviewed. For things like sleep hours, I average them across the time period. For basic tasks like stretching, I'll list 10/12 – meaning I did it 10 days out of the 12 I reviewed.

    Rest of the post is spot on – but I'd say definitely don't discard weekly reviews just because they don't happen every seven days.

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  20. @ericnormand says:

    I think the biggest thing that has helped me with my projects is to plan them better.

    I don't think GTD goes into this, because it's basically a fancy way of managing your planned projects, not a way to plan projects. The mistake that got me was thinking that just writing down a bunch of next actions *was* planning. It is not.

    When I have a new project I want to start, I plan out its scope to be as simple as possible. First I list out all of the features of the project and minimize the list to the simplest list possible. I move all of the items I won't get to to another page for v2.0. Then I break the v1.0 steps down into next actions.

    I don't mind going over 2 minutes on my next actions, because sometimes it's just difficult to break stuff down that far. But I do break them down to say, an hour or two. That sometimes means breaking down a task that seems atomic into several tasks. But I make sure that each 1-2 hour block is meaningful to the project and well-defined, so that I get that high of accomplishment when it's done. I consider the feeling of accomplishment is vital to sustained effort on the project.

    Thinking a bit more about each of your todo items is key. When I first started GTD, I'd just write down all of my ideas into todo actions with no focus or plan. Plan it out, throw away most of them, and feel get more done.

    • ryanwaggoner says:

      Hmm…I agree that GTD doesn't focus on the planning stage too much, but I haven't found that to be an issue. I rarely plan out my projects A-Z at the beginning. In fact, I find that counterproductive, as it makes adding new projects a huge task that I put off, it removes flexibility, and it's often impossible because I don't know all the parameters of the project. Instead, I keep an eye on my projects to ensure I always have at least 1 next action. When I run out, I look at what needs to be done next and add those steps.Also, I don't recall GTD ever stating that next actions should be 2 mins. I routinely have 30-60 min tasks. Rather, GTD says that when processing your inbox, if an item takes 2 mins to do, just do it.

  21. GregPK says:

    >> Actually do my weekly reviews

    Well duh!
    I don’t have a copy of the book handy, but I’m pretty sure that in the audiobook D.Allen specifically states that this is THE most important part of the system. I’ve fallen into this trap a lot of times, and it always boggles my mind how such a “small” thing can have that much effect on the system.

    My educated guess is that everything will fall back into place once you go back to the reviews.

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