The ultimate to-do list system

What is the ultimate to-do list system?

I wish I knew. Seriously. I’m looking for it.

Many of us use the word “ultimate” to mean utmost or maximum: “the ultimate basketball player.” But ultimate has long meant last or final, as in “ultimate destination.” I’m searching for the final to-do system, one I will use forever.

Over the years, I have used a variety of to-do systems. As a lawyer, I need a to-do list system that works. I’ve used the Franklin Planner method (before Franklin ever joined up with Stephen Covey), similar tools on an early Palm handheld device, applications on my Mac, my Newton Message Pad(s), legal pads, variations of GTD, Circa notebooks, Moleskine notebooks, iPhones and my iPad. I’ve used OmniFocus and Things. I can’t even begin to count how much money I’ve spent on various to-do systems, looking for the right one.

With each of these systems, I have a similar experience: I get all my stuff into the to-do system, and then it sits and ferments. Grows mold. Whatever you want to say. Self-imposed deadlines pass, new stuff doesn’t get added. At times I don’t want to look at the to-do list because I don’t want to see all the stuff that’s on it.

Most lawyers wouldn’t want anyone to discover that they have these problems with the to-do list, but I figure nothing good comes from hiding the issue. Things do get done, just not as efficiently as I would like (and I rarely have complaints from clients about getting things done quickly). It seems to me that my bigger problem is a combination of procrastination and lack of discipline. I think if I had a to-do system that confronted me each day with a “here’s the stuff you must do today, and I’m going to pester you until it’s all done” message everything would be great. (It would also need to pester me at the end of each day to put new to-do items in the system!) Hmmm…I think what I may need is a mom in my office. 🙂

What do you use for your to-do systems? How do you maintain them? Who pesters you about them?


13 thoughts on “The ultimate to-do list system

  1. There is a very simple trick here. Spend the first part of your day driving your inbox down to zero. This is most easily accomplished by being able to drag relevant emails into tasks to create them, and then again to file them (which outlook for windows does extremely well, nabbing attachments and everything and outlook for mac does not do at all – not sure how you can make this work with what you have, but it is a key step). Anything that is in an email that is actionable in under five minutes gets done on the spot. Everything else gets filed either into reference, or reference plus a task. Now you have a totally empty inbox. So what are you going to do? Go to your to do list and start getting stuff done!

    1. This is a good tactic, Christiana. I’m pretty good at keeping my inbox at or near zero. At most, I might leave a message in the inbox if I am waiting on something before I reply. You’re right about Outlook on the Mac—its feature set stinks compared to its Windows counterpart. One way to accomplish something similar is to use Evernote, where you can forward an email (with attachments) to Evernote, put it in your task list, as well as have it filed away there.

      The tricky part for me is getting into the regular habit of actually using a to-do system every single day. As it is, I float from system to system, constantly starting over in a sense. Perhaps I should just accept that I’m likely to become bored after using a system for a while and be ready to start with another one that’s in waiting.

      1. Perhaps? But perhaps you would get to love a system if you really committed to spending enough time with it to make it work perfectly for the way you work. That is what happened for me anyway. But then again, I am not the type of person the get the first-generation of anything (except, apparently, Outlook for Mac!).

        But it occurs to me that perhaps a bigger issue is that your work is more long-term and project based? Mine has generally been very short-task oriented, which makes a to-do system a greater good.

  2. Being “inner directed” is an old-fashioned term who’s meaning changes with the times but there is no substitute for self-discipline. It is rather like brushing your teeth after a meal or putting gas in the car. Habituating working from a “to do” list can be accomplished in two weeks or so when a person accepts the fact that it is beneficial to them to do so. I meet with myself on a weekly basis and plan the week along the following guidelines: what I have to do, what I want to do, and projects for the future including both think time and actual work time. At the end of the week I evaluate what I got done and when an item is on the list for a few weeks I ask myself if it is important enough to keep on the list or if I am kidding myself that I need to do it. There is no easy path to self-discipline but to make and list and do it, even if it is a little bit at a time.

  3. I totally recognize myself in your post. The quest for the perfect todo system is something I spend far to much time on. I have also tried things and omnifocus, nirvanahq, fire task, wunderlist,, astrid, orchestra…the list goes on and on…

    The biggest problem in my case is that when I’m on a roll I tend to get entry of stuff done, but after a productive day, I don’t really keep track of what’s been done and not. This means that I can’t trust my system since I’m not sure if the things on the list are completed already.

    This is of course my own fault, and should be fixable…but I haven’t succeeded in it yet.

    My requirements for my gtd system is:
    – simple
    – email to inbox
    – good looking
    – fast
    Beyond this, it should be able to handle contexts and projects. I have to say I haven’t found the perfect app for this yet…

    1. Thanks for your comment, Andre. Six months later and my “search” continues. I’m pretty sure the problem isn’t the system or app, it’s the inability to make a solid habit or practice of using the system. One of the stumbling blocks for some folks may be that no app/system can be as immediately accessible and omnipresent as one’s own brain. If I have a main system, say on my laptop using OmniFocus, I can sync it with my iPad and my iPhone.

      But even then, assuming I have my iPad or iPhone with me, I have to turn it on, launch the app, type in the entry, and then finish using the app. Not a burdensome process, but definitely not as easy and quick as “remembering” it. (I know, I know—it’s very easy to forget an item.) I could write it down in a notebook, but it would still have to be transferred to the main system so it gets into the one trusted location.

      Ernie Svenson of Ernie the Attorney reported not too long ago that he’s taken to using OmniFocus as his main storage system for to-do items, but then he will use a piece of paper to prepare his daily to do list using his OmniFocus as a master list. That’s also appealing to me.

      But again, I think it all gets back to the issue of using the system consistently and not intermittently. Maybe what we need is someone willing to pay us a hundred bucks/euros/whatever each day if we’ve used the system. Absent that, I think I may add using my to do system to the Lift app I wrote about earlier this month. It’s helped me be more mindful of the habits I’m trying to develop, even if I don’t practice the habit each day.

      1. Nice reply. I will for sure check out Lift.

        I just find it funny how many people struggle with this Gtd/todo/productivity mayhem. I find myself searching the web for hours trying to find the perfect solution, but I guess I should be better off just using my time doing stuff 🙂

        Maybe if we together tried to figure out WHY the system keeps breaking down, we could find the best way to tackle the problem? I agree that time is a factor, just launching an app takes way to long time in comparison with just remembering it. Siri is a great way to add things quickly, but since I’m Swedish people look with confusion at me when I speak English into my phone.

        Another thing that I find hard is to keep the system up to date. As I said earlier, just keeping on top of what things are done and what things are yet do be done is hard.

        I think that’s two of the biggest obstacles for me;
        1. Adding stuff fast enough (on all my Apple devices and a windows computer at work) and,
        2. Keeping the system in order.

      2. I also wonder if the dilemma we describe isn’t a form of procrastination. Lifehacker usually has some interesting posts about defeating procrastination. Here’s a recent one.

  4. Well, at least we all know we are not alone! I’m also on the quest and have also used just about every task management tool (and have also spent loads of money). Key problems for me is that I struggle to not be driven by incoming email. I try to aggressively sort it and “task” it so that I can keep my inbox at zero and at least deal with it with some kind of prioritisation. I respond immediately to the things that require 2-5 minutes of effort. However, I’ve found that mentally once I put that substantial email somewhere (as a task or an email in a special folder), I somehow feel that I’ve dealt with it and I can just about spend the entire day doing those 5 minute tasks on often trivial emails. Result is that I spend the whole day answering unimportant email and stick the important stuff away somewhere to be forgotten until I get an angry reminder from the sender.

    My current theory is that I quickly get to a point where the task system (e.g. Things) becomes a repository of stuff I’m ashamed about not having done, so I become less inclined to look at it. It is just another thing to sort out. Likewise, if I use Mailtags and smart mailboxes etc and sort my mail, I end up with folders that are similarly crammed with stuff I find painful to have to go sort through. The one thing I can’t avoid looking at is my inbox, so maybe I can handle incoming mail by …

    a. deleting
    b. doing a quick response (I’d say sub 1 minute)
    c. annotating, setting a date, identifying any dependencies, creating any associated tasks and effectively saying “send this to me again when timing is right”

    … and then I can just handle everything from my inbox?

    Still experimenting

    1. Tim, thanks for your comment. You’ve touched on some thoughts that I recognized in myself, even if I haven’t been able to articulate them.

  5. What I see here are two people/men who are having the same difficulty and it starts with the supposition that there is a perfect system to be found. It is more likely that you will have to adjust your expectations and realize and accept that there is no perfect anything…job, relationship, task completion system, etc. There will always be more to do than can be done in a day or even a week. Just accepting that will make a big difference in the attitude and the time and money wasted on looking for a perfect system can be better used to just keep on plodding along.
    I do have a suggestion…why not get another email address solely for those people who you absolutely have to answer relatively quickly. You might have to forward some emails to this new address so it remains somewhat confidential but that sounds workable.
    I am definately enjoying reading how this is playing out in your lives. I am less stressed when I realize that perfection doesn’t exist and I am allowing myself to be human and err occasionally.

  6. I can’t tell you how encouraging it is to hear that there are some other professionals struggling with the same issues i have regarding their to do system. I have at least gotten better at wasting time sifting the internet searching for and installing the latest system. I have virtually given up the search. Well, maybe I thought I had but I guess I did do a search and find this article! I currently use Outlook, Evernote and (not to mention the built in system in our web-based project management system at work) and I was hoping to find a solution that might help me just settle on one or at least two. The Outlook system is good but it doesn’t work across all my platforms. Evernote does, and it’s great for attachments and reference material, but it’s not really a true to do system and so I don’t use it for routine things like “pick up coffee”, or “call the boss”. Also it doesn’t do recurring tasks like “pay mortgage”. comes closest to the “push” system that you seem to e looking for as it has a routine that runs through your list at whatever time you assign, say 7am each day. BUT, it doesn’t have attachments.
    So I struggle with three or four lists in different places and feel less disorganized than my wife, who uses no system whatsoever other than her brain and notebooks. I keep going back to Evernote but like you, I can’t seem to get into a routine for checking the open items. So it must be a discipline thing. It’s funny that we always seem to make it to meetings that have other attendees, but we put much less effort into making meetings with ourselves to review and plan the very important things in our lives.

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