Long-range projects, aka. The Grind

I admire people who have lists of things to do during the day, and can check those things off and move on. Or even a template for a project with all the steps laid out. That drip feed of dopamine from checking those boxes must be super good.

What about you folks that have projects that last for months or years?

For instance, an item I’ve been working on for the last month “work on statistics for Aim 2”, which is part of the larger Aim 2 project that I’ve been working on for years.

Figuring out what to do is part of my “doing”, so it’s not like I can make a checklist. (unless I’m Dunning-Krugering myself)

Do you all just block off time, then work that time and close up shop at the end of the day feeling satisfied that you worked or spun your wheels for the allotted time?


I use Omni Focus to management my projects.

On a Friday each week I plan for next week. I block out time for Deep work (where deep concentration is needed) and book specific work into those slots. I also book in time for Shallow Work (admin work mostly and email handling)

if I have longer term projects I try and keep them moving by working a little on them each week either on Deep Work or Shallow work depending on the tasks required.


Solely my own experience: Every project I work on, regardless of duration, can and should be broken into milestones, chunks of shorter duration. And those should be further decomposed into tasks that are building blocks for achieving the milestone. Tasks should be time-bound and have a defined end state.

For me, “work on statistics” is not a task. If I were doing this, I would try to define what the intended outcome of working on statistics today is, and a different outcome for tomorrow, and so forth. Or maybe I would see that working on stats is not the task to track, but merely a means to accomplishing that task?

I create a personal dashboard to measure progress against this week’s tasks, the milestone they belong to, and the overall multi-year project – something even as simple as a set of goal thermometers, then you can begin to visualize progress. That is good for a few hits of dopamine.

I use a whiteboard for that. OmniFocus and others suck at providing a simple, punchy visual affirmation of progress. Checkboxes with tick marks are not motivating for me.


For projects over months: Kanban boards across areas of responsibility with Projects in swim lanes (flight analogy: Scheduled, Postponed, For Tower Clearance, In Flight, Grounded, Landed). Using Curio. Projects tied to the respective task list in OmniFocus.

For a recent publication completed over a year: A project in Curio with its own Kanban board.

You must have a result that you must validate. You must have a minimum threshold of an amount of data that you have to analyze to meet a certain confidence level. You must have a specific formulation that must be translated analytically from its equation to its linear propagation format for the relative uncertainties. You must have something that must be achieved as a milestone in this “work”.

How do we eat an elephant. One piece at a time. Where is the leg, ear, trunk, tail … in this “work on statistics” (“consume an elephant”) statement?



I think my situation is similar. I have figured out that I have two configurations of "things that do.” One configuration is things I do and can check the off the task list. The traditional GTD next actions.

The second configuration is things that I have to invest time in but can’t check off the list - at least not for a while. There is often no discrete next action that I can identify.

The second configuration is hard to deal with from a management-tools perspective. Some of these things can be broken into sub projects that look like next actions under the first configuration. That’s easy enough. I can track those like normal.

But how do you have a task for “invest time on x”? Just a handle that as an appointment? But then how do you actively manage such a project to ensure you are moving it toward completion—however far away “completion” may be?


First off all, I admire people who commit to the long term. It gives me anxiety thinking of a project that goes over years. (Even though I have them)

I have strong project notes, and I plan milestones, but focus on the next chunk. It’s the only way I can not feel overwhelmed and push it off to the future, where the deadline exists in the nether.

Mind maps help to start, then outlines, then milestones. That helps me to feel good.


It depends on the project. I make some long projects shorter and easier by procrastinating and ruminating on them as long as possible. I’ve saved literally hundreds of hours of programming on one project by putting it off until I thought of or came across a better approach. Hill Charts in Basecamp/Shape Up are a tool that models this kind of progress nicely, but I haven’t had a chance to work with people who grok them yet.


When the work is more predictable and of sufficient quantity that saving time, in time, is unlikely, I break it into chunks in OmniFocus, if a solo project, based on some higher level goals. More commonly, I’m working with a team and the milestones live in some kind of shared-access software so I manage it there. We have a fantastic team at work that will schedule long-term milestones in our main operating software based on scheduling templates that I contribute to.


That “sleep on it” approach to programming (which I did last night) or writing (which I did the night before) works wonders.

Certainly gets you out of the fug.

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Every project, regardless of duration, can and should be broken into milestones, chunks of shorter duration.

I wish it was true, but it’s globally false for most artistic projects. Novels for instance cannot be cut into chunks of “finish chapter x” or “outline z” because there are so many interdependent and moving parts than the process is not linear but overwhelmingly emergent. A chapter is not a meaningful unit of work despite the appearances; as Sir Terry Pratchett said “the first draft is only there for you to understand the story”. It’s a continuum of clarity that only gets you from beginning to end. After having written a chapter, you may realize you have tackled a whole plot line wrong and you have to redo most of it. Is the chapter a failure? No, it taught you what you needed to really do.

Sure, you can cut the process into “outline - write - revise” but it’s so vast that it’s not helpful.

I work on the multi-year projects that books and series are through time blocking. It’s actually both very simple and a boring system. I book (heh) 4-5 hours per day to “keep working on book x” and through regular and diligent effort, a book comes out at the end.


I remember being surprised when I asked an award winning author of young adult fiction about his creative process for stories and writing. While he was quick to suggest that mind maps, outlines, 3x5 cards, etc., were important tools, he didn’t actually use any of them. His goal was simply to write 2-4 pages every night (after his day job teaching) and through that process develop the stories and subsequent books.


Sorry to offend. Comment removed.

Hey, no! No offense taken! We’re just discussing here! You provide a point, I just nuance it, that’s the way it goes!

It’s me who’s sorry if I could imply I was offended. I assure you I wasn’t - we’re just talking here :slightly_smiling_face:


Honestly, these days I think I build an outline just to be able to throw out the window (but have a safety net if needed) :sweat_smile:


Your comment to me, since deleted, was very helpful. I just did a screenshot of it (resurrected with the “pencil” button) to refer back to it. And based on your comment, I’ve been trying to solidify the next steps I want to take today.

Everyone’s comments have been helpful. I think maybe there’s a “dual process” here. There’s the creative perspective, à la @KillerWhale et al. , and there’s the task/stepwise perspective, à la @quorm et al. Somewhere encompassing those two is probably The Happy Place. Structure and freedom.


Yes, also glad to have read quorm ’s comment. And I agree there needs to be some fluidity to managing projects of this time range. Creating or abandoning structure as the nature or the project changes, or as it becomes evident, without losing the drive to complete it and the ability to report on it to whoever controls the money, is a useful art and science.

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I’m probably the epitome of long term projects. Here’s an example of one. Fencing. We had the first game damage fence from the DOW in our area. But by the time we moved back in 2000 is was way past its use by date and needed replacing. First we had to deal witht egetting rid of the lien from the DOW for the old fence that was falling down. build a suitable temporary fence to keep the sheep safe and get on the schedule to get the new fence built. We started the process in 2003 and the last segment of fence was competed in 2017.

The first set of things was to survey prices, investigate the options for a DOW sponsored fence again and work on locating fence builders. We also planned the project in into single line segments and ranked them on the importance. That part alone took almost 3 years.

So for example the first fence to be finished was a lower regular fence in the back cedars. The reason was that that fence was still all barbed wire and meant we could not move the stallion out there. So getting it done would increase the pasture area by a bit and give us more freedom in where the horses could live. Plus it allowed us to see if the selected fence builder was any good. Anyone who can build a straight fence on our mesa with all of our rocks is a top notch fence builder and the guy we picked passed with flying colors. That fence segment got done in 2006.

We can only work on fences at a few specific times of the eyar. It has to be after snow season, before it gets too hot and we need to have a way to protect he sheep while the fence is down. Some segments also require a bulldozer to be scheduled to move rocks.

What I did to keep at it is spend a lot of time on the plan and then, since I am motivated by checking off things I made as many small things as separate actions as I could SO every phone call, every step and for the things where the action would take months I made a worked X minutes or hours on action type of actions so I could check them off.


Yes! Whenever I read or hear you talk about your projects I start sweating lol. And if I remember correctly, you take stuff out of your database and put it back it in Omnifocus right? I’d lose everything so fast lol.

This helps me a lot doing my stuff because it helps me to conceptualize something concrete and not something abstract.

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The Cal Newport book Deep Work, should help you with this.

But to give a quick answer, I schedule 1-2 hour blocks of time during the day for this Deep Work, which for me is writing software, but could just as easily apply to writing a book. I’m using the app Sorted and at the end of the 2 hour block, I check off the box next to “Work on feature X of application Y”. You could have a 2 hour block of work on chapter X of novel Y.

Link for Sorted


Sort of, I keep my non-active things in a series of DEVONThink notes.
Omnifocus has the current season active projects and I reset it on the solstices and equinoxes.

That’s how lots of my multiyear projects happen, things that can only be worked on in a specific season get worked on during their time and then put into hibernation until the next time I can work on them rolls around if I haven’t finished them by the end of the season.


I struggle so much with this organization and this kind of work.

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