How to handle too many overdue tasks?

As the title says, I have OF2 set up so that my projects have due dates, and the tasks within them have more granular due dates leading up to the overall project due date.

Every task in the project is sequential, so A must be done before B, B before C, and so on.

The problem is that when I set up my projects, I was over-zealous in setting the due dates, confident that I would be able to meet them in order. Sadly, I have not been able to meet the due dates on some projects at all. Every day, the list of undone tasks grows longer and longer, and I see myself getting further behind. It’s like a bad dream or something… and one that I’ve created.

I know that it’s possible on OF2 for Mac to defer selected tasks in one fell swoop to a certain date, or to put projects on hold. However, when I select a project and then click on the “+1 week” in the “Defer Until” area of the sidebar, every task in that project gets deferred to the exact same date… all of the staggered due dates I had painstakingly set for that project are lost.

Aside from setting more realistic deadlines and goals in the future, I wonder if there is an effective and simple way to simply slide the due date of every task in a project forward one week, for instance?

More generally speaking: what’s the most effective way to clean up and handle several dozen tasks that have changed to overdue (red) state after reaching the deadline?

Any insights would be appreciated and welcomed… including philosophies on how to best use the software for scenarios like staggered due dates in a project, delaying entire sets of tasks while keeping their overall sequence intact, and more general approaches to meeting bigger goals in life by setting smaller goals…


One clean up is to set Due Dates based on external limits. It seems you are setting by internal desires. When you WANT to do something has no bearing on when you HAVE TO do something. It is the Urgent or Important metrics in the 7 Steps mantra.

Another clean up for granular action groups is to set a Due Date only on the outcome. For each review period, you then get to decide whether you will be a student in college who does everything in a last minute sprint or a methodical builder who builds a Gothic cathedral over a decade span (but compressed for your given action group perhaps to 10 days instead of 10 years).

FWIW, as an overall perspective from an outside observer, your approach seems to be to fix all the back-end decisions about what you will do at any given time during your front-end stage of looking at what you have to do overall to complete any given project. Heaven forbid and good luck when your SO or spouse or kid or dog or mother-in-law or … interrupts that workflow processing method in action.


Thanks very much for your advice and comments, DrJJWMac.

I can understand the distinction. Definitely, setting granular “sub-goals” is based on inner desires, I would agree.

For instance, I have a goal of composing and recording a collection of new music. Obviously this is a daunting goal that requires many sub-tasks, so I have broken it down into very granular steps, even going down to the small keyboard exercises I need to learn to improve my technique, or the elements of synthesizer programming I need to master, or the video I need to watch to get a better grasp on using Logic Pro for digital recording.

I have set the final objective as a five-year goal, and broken it down into two-year goals, and then yearly goals. For this year’s objectives, I assigned a due date. Then, I broke the goal for this year down much further, with all kinds of subtasks… and I put a due date on each. As you wrote, it was all based on internal desire. The whole project is a “would like” and not a “must do”. The goal is important for me from a creative standpoint, but no, there are no managers standing over me, telling me that I will lose a contract or get fired if I don’t do this by month XX. So, based on your idea, none of the project would have a due date, since none of it is “urgent”. In fact, I could safely never do the project for my entire life. The only effects this would have would be on my psyche, knowing that I never bothered to try… and that is probably a more powerful punishment in the long run than any dock in pay or loss of gainful employment.

Yes, I agree—that would indeed clean things up. What you seem to be saying is that I should remove the due dates on everything but the final objective. In that case, OmniFocus would be more like a guidepost, an outline showing me the steps to reach the objective… but there would be no guidance in terms of “when”. I would know that there are a mountain of things left to do before recording my album, but the rest of it would be left to my instincts, since there would be no detailed schedule or time guide left.

From a motivational standpoint, I thought it would be more useful to have those weekly goals, and then those monthly goals, all in support of larger yearly and five-year goals. However, what you implied about distractions to interrupt the flow holds weight. In reality, my productivity tool (OF) and system is not helping much. It did at first when I began the project. I was full of energy and enthusiasm, seeing that I had very specific goals and knew exactly when I needed to finish each one in order to achieve higher and larger objectives. This worked for the first three weeks or so. Then, as you wrote, everything changed. There were distractions, illnesses, lots of freelance projects coming that I needed to do to pay the bills. The tasks in OF kept piling up as the due dates slipped away one by one, and I had less and less energy to complete them. Now, every time I open OF, I am bitterly reminded that I could not follow through, that I let life’s distractions get in the way. My day job, my family, my level of energy… everything contributed to preventing me from dutifully ticking off those well-meaning tasks. I feel like a failure.

I realize that I’m not a machine, at least not a reliable one in the tried-and-tested mechanical sense. ;-) Suppose I keep the whole project as-is, but remove all those due dates. What I would have left would be a single, final due date that applies to the whole project. Considering all the distractions, it would probably take me ten years instead of five years to complete. Maybe that’s “reality”, but I guess I have a hard time coping with the fact that there really isn’t enough time and energy to “do it all”. In that case, what role does OF play? Just an outline and progress tracker, perhaps? Even that is sort of useful, I suppose, although it doesn’t tell me how much effort and energy I will really need before I come to the end of the road with the project.

It’s hard to know how to best use this tool in order to achieve very organic, human objectives based on simple ambition and desire. I’ve considered even not using any tools like this at all, and just winging it entirely. That might free up my time spent in organization. It’s just that perhaps I simply don’t trust myself to finish or to stay on course. I want to know that I’m on the right track. I’ve come to like to have those guideposts and lists of things to do along the way. It seems logical to have the process listed up and outlined, in order to achieve your objectives. That’s what OF helps people do. Perhaps I’ve taken it too far…

In my opinion, even these projects should not have a due date, unless it is a true due date - i.e. an externally driven deadline with associated consequences.

Another way to look at it is simply acknowledging that priorities change, as do circumstances. For better or worse, you can not know what your situation is x weeks/months/years from now. Measuring yourself against deadlines you came up with at a time you didn’t know that adds a level of stress to your productivity approach that I feel is exactly what the GTD approach is supposed to avoid.

I recommend reading the David Allen book if you haven’t yet, but I can tell you that for me personally it does 2 things above all else:

  1. It provides me with the peace of mind of a “trusted system”. i.e. if
    I am managing my system right, everything that I don’t want to
    forget is in there.
  2. It allows me to see and focus on exactly the
    tasks that make sense based on my current circumstances and
    priorities, without being burdened by all the tasks I can’t or don’t
    want to do right now.

Another point about due dates - If something is past due, it shows up in my Forecast View and in the custom perspectives I set up for it, marked red. I only want to see tasks in red that have actual consequences if missed (e.g. bills that are due, documents that need to be renewed) - without having these diluted by tasks that I have set due dates myself and that I can just defer. I would be too concerned to make a mistake in distinguishing the two and dropping the ball on an actual deadline.

Hello Khaberz,

Thanks for your reply.

This is an interesting approach, but one that seems to go against the grain of what conventional goal-setting methods say. I’ve heard it said that without a time limit, there is no sense of urgency. For that reason, I thought it was important to set deadlines and due dates for everything. However, in practice, that didn’t work well. Maybe it would be fine for a computer doing a cron job at a specified time every day, but not for human beings, when things can and do get in the way. The more complex and involved the project gets, the greater the chance of slipping behind somewhere. That’s a lesson I’ve learned time and again through painful experience. I just wonder what the alternative is to not setting due dates to groups of things I want to get done.

That said, I recognize that what you said matches David Allen’s GTD approach—don’t set due dates unless it’s something that absolutely needs to get done by a certain date.

Good point. Yes, you are correct about the level of stress inherent in setting deadlines, and the measuring yourself by them. We do it all the time at work—clients or managers or coworkers want something by a certain time and date, and our efforts are directed towards the goal of providing them with what they asked for. In those cases, you might be requested for something nebulous (“make a presentation to introduce this new system to the people of XX division next Monday”), but there are invariably detailed steps that need to be followed. The deadline is always there, but the internal processes required to meet that deadline could be entirely flexible and lacking due dates of their own.

I have actually read David Allen’s “Getting Things Done”. The main points I got out of that book were about how a “project” consists of two or more things to do, and also that getting things “out of your head” and “into your system” is supposed to provide some sort of relief. I’d like to go back and review that book. I also felt at the time that the task and project outline model that OmniFocus offers was a bit different from what David Allen’s system recommended, and it seemed that OF needed some tweaking and workarounds to “make it work” with Allen’s GTD… but that’s just what I remember.

This is an excellent point, and I’d totally agree. I’ve felt a lot of confusion and frustration with the system lately for this reason.

In point of fact, there are psychic consequences to not achieving personal projects and goals that you set out. For me, trying to create a completed collection of original music is a project that has hounded me for many years now, and until recently, I haven’t been able to really make it happen. I used Things for a while, which seemed much closer to Allen’s GTD concept and easier to adapt, but I felt that OF offered the structured outline that I wanted. The problem has been due dates and deadlines, as I mentioned. If something is important to us, even if it’s not a bill that needs to be paid or a delivery of a project for a business client, why draw distinctions? If we start tacking due dates on things in life that we “think” are important and then relegate the rest as “someday” or “next actions”, how much are we actually going to tackle?

In my experience, I’ve come to see that the act of setting due dates and trying to abide with them for nearly everything in life is fraught with so much stress and disappointment when I can’t “measure up”. Yet nobody enjoys eternal life here on this planet, so the element of time is always a factor. The ultimate “due date” is the day we die, and everyone has one. But there are more subtle due dates that we often forget about, such as the day when we can no longer do the things we want to do, for physical or mental reasons. The older we get, the more pressing our needs to actualize ourselves as human beings becomes, if we are at all concerned about improving ourselves as human beings. So from that perspective, it has seemed logical to me to set those hard due dates even for things in life that don’t require them. The problem is that they are artificial due dates, and mostly based on arbitrary divisions of time (years, decades, months, etc.), and they don’t consider physical and mental energy, other things in life that come up, etc.

Perhaps GTD encourages us to live more in the present day, but I also wonder how you can really get anything done when your focus is always shifting to what seems interesting and good on that day. That’s why OF has tended to make more sense to me as a productivity tool than Things—the outline is there, and it’s really more like a topical approach to what you want to accomplish in life, rather than a grab-bag of stuff that “should” get done (the “Next Actions” group) or “must” get done now (the “Today” group) or “might” get done (the “Someday” group). That doesn’t mean I’ve been successful with either tool, though. It’s refreshing to “get it all out”, but there’s still something there in the execution and implementation that I seem to be missing.


I look at it this way: The more time I invest overall in getting “stuff” done, the more I advance my tasks and projects. What tasks I spend this time on is mostly situational - my energy, what I feel like doing, what project I want to focus on now. Due dates - unless real - don’t motivate me. They stress me out. Knowing I am spending my time on the appropriate things is a better motivator for me.

I use the flag - rather than due dates to reflect this in OF. If I decide to spend my weekend on projects X and Y, I’ll flag these projects as a whole of particular tasks in them, they show up in the custom perspective I set up until I complete the tasks or decide to shift my focus and unflag them.

I agree with your assessment - time is the key parameter - but disagree with your way of implementing it. Setting a bunch of deadlines does not make me invest more time on being productive, nor does help me spend the time I invest more productively. Working on the right things at a given time does.

Thank you for the detailed response. Rather than going line-by-line, I will respond in general terms.

First, I suggest by analogy that it seems you are trying to use OF in the same that way someone might try to create a universe with a program that only defines characteristics at an atom-by-atom level. OF is a great tool for the atom by atom level of getting things done. Frankly, I find that it otherwise sucks for planning big-picture layouts. Not that you cannot put a big picture in to OF. Rather, you cannot translate a big picture easily in to OF by building that big picture atom by atom at a time. This is especially true for such big pictures that span the equivalent scope in goals and the equivalent completion time frames that you have in mind. Essentially, to build the Gothic cathedral that you want to complete in the next five years, you need to have some other project management tools around to track the big picture. Do you have any tools to layout the big picture of what you want? Some examples include Omniplan, Goalscape, or mind-map apps.

Secondly, what you have in mind sounds like a college curriculum development. Nothing is wrong with this. In fact, I applaud that you seem to have this apparent level of overview right now. What I find difficult to fathom is that you believe that you have to plan the details and nuts+bolts to that same level over the entire five years in order to be “successful”. When you see this, you might think about the overwhelming extra challenges that a college student in your proposed curriculum would face because every time step is micro-managed to the nth degree. Have you considered to step back instead and to plan your goal more formally along the line of a college curriculum? In particular, after you have a big picture, break down in to yearly and then “semester by semester” and then “course by course” levels. Best would be to work from the end backwards. Goals beget objectives that beget milestones. Milestones beget metrics and objectives beget self-encapsulated, semester-by-semester course projects to build a curriculum. Individual course projects beget their own assignments and tests. At this level, you set proposed due dates. Once you see this analogy, then your granularity filter changes completely. Meeting daily due dates that you initial impose from untestable dreams and desires becomes less important than meeting well-structured course objectives and ending with well-defined and measurable course outcomes. Once you have metrics for a given course, you can think also about setting “grade levels” against those metrics. Grade levels are factors that allow you to rank your progress in a given course during and at the end of the course. Once this picture cements for you, you set up and do a course over a given “semester”. Along the way, your due dates are set on the assignments and exams that you place for yourself. If you do not turn in an assignment when due, then you get a failing grade for it. If you met the due date, give yourself some level of “grade” for the assignment. Plan some type of “exam” to test how well you have done, and give yourself some type of “grade” for the exam. At the end of the “semester”, tally the grades and assess from them rather than from how many due dates you have met or missed. If you feel, based on the grades, that you have passed a given course for that given semester, then you permit yourself to plan for the next course sequence in the coming semester. If you feel you have failed the course, then you plan to repeat it in the coming semester. In this analogy, a semester could be a span of 10 weeks or 10 hours or 10 days. It is set by whatever cycle of time you feel is needed to master a given set of course outcomes.

In conclusion, what I think you need is a paradigm shift in how you put together and use software tools to help you go successfully from where you are today to where you want to be in five years from today. I hope this general picture, rather than a line-by-line response, is helpful in that way.

Hello DrJJWMac,

Hmmm, I may have an old version of OmniPlan and perhaps MS Project for Windows, and I also have MindNode as well. I think I see what you’re getting at—if you want to create a project for which the “big picture” is required, OmniFocus is not too appropriate as a tool. I guess that after all this discussion (which has been very useful in and of itself), I’m feeling less excited about planning everything down to the letter for the next five years.

Indeed—college curricula might be “managed” or planned in the way you mentioned, and now I’m starting to see that it’s the achievement of the objectives that’s more important than the “daily due dates”. I’m also starting to see that planning and executing a creative project for myself may not need such a high level of planning. In fact, I imagine that I would instinctively know what to do based on experience, and when to do it. I thought that having a formal outline would be a motivating factor, and having those due dates would help me stay on track, but it is indeed the content of what is “learned” that makes the most difference, not on how well you met the due dates.

In fact, it’s interesting you should compare the “scholastic achievement” approach with the “staying on top of the due dates” approach. For instance, in trying to improve my keyboard performance skills, I planned to achieve a long series of rhythm and technique exercises that a previous instructor had recommended. It ended up being just a rat-race to meet the due dates, and I didn’t get as much out of each exercise as I wanted.

Thanks again for your intriguing approach. There’s a lot to think about there.


Hello khaberz,

Good point. One of the toughest things for me about the GTD system as proposed by David Allen is deciding on what to focus on now. As you mentioned, it depends on your energy level, what you feel like doing, and so on. Due dates haven’t done much for me, either. The flags in OF are sort of useful, but primitive. I usually end up putting out all the work-related “fires” first during the day, and then whatever energy I may have left goes towards the other stuff.

I’m in the process of rereading the GTD book to see if there’s anything I might have missed. Thanks again.