Killer Perfectionism

Hi friends!

I have a new question for you: I’m always tweaking my OmniFocus entries. “This should be in this context instead of that one.” Or doubting the scope of my next action: “Is ‘walk to my car’ granular enough? Maybe it should be recorded as ‘Take the first step toward my car’ instead…?” Or project planning “Well, this is a step toward that goal, and I should record that in the project planning view, and that applies to my overall goal of being an actor…”

Forever. There’s so much focus in this method of “well when you have a complete list of things in front of you, make an intuitive choice.” But the problem is: I never feel like that list is complete, and the work required to get it to a level that might be complete takes more time than I have available on any day, ever.

Does anyone have any insight on still using OmniFocus and GTD effectively and comfortably while dealing with the effects of perfectionism and OCD?

Use the Force, Luke. :-)

I appreciate your question. To add perspective, I have taken two different years to iterate through and stabilize my context lists and my methodologies in OF. The balance you absolutely have to strike is to learn when to say NO MORE TWEAKING AROUND. How you do that is your own path forward.

I might recommend that you find a set of contexts right now that seem to suit your approach. Set them up and demand of yourself to stick with them for at least the next six months. In addition, take a day or so to practice setting up projects with a narrowed-down core list of actions. Determine the nominal set of actions you typically need. Then, with every future project, resolve to generate no more than a minimum set of actions in it. Finally, in cases where projects seem too open-ended to resolve yet, I suggest to fall back on this “template”

Project XYZ StartUp (sequential)

  • define the problem (context: define)
    –> what is the problem, and what will you get by doing it?
  • gather the background information (context: research)
    –> do you have all the information you need to solve the problem?
  • layout the steps (context: plan)
    –> what sequential and/or parallel actions are needed to go from start to end?
  • finalize the project plan (context: close)
    –> approve in your own mind that it is “set in stone” and ready to be done (rather than tweaked)

With this, you may be able to avoid making a project that forever get more actions added to it and seems never to have an end.

As the saying somewhat goes: “The search for perfection will always be the death of an otherwise adequate accomplishment”.



JJW, thank you. This is exactly what I need to hear and exactly what I don’t want to hear! I’m thankful I finally decided to post on a forum and that you’ve been willing to help me with input, I’ve been trying to sort this out myself for two years but just digging deeper. I was dreaming that OmniFocus might take the vagueness and confusion out of my life, if only I had it set up just a little more properly. It’s also difficult to have GTD ask me to shoot for “bright lines” but at the same time realize those lines are all set by me, a much less confident and decisive person than I’d like to be.

Thanks for the example project, I like that your contexts basically are the verb that start the action, I put a lot of concern into getting those contexts right and I might not need to work at it so hard.

Do you know of any example OmniFocus setups that are in a “ready” state, so I can just see what works for others?

Do you have any input on how high up I should go in the project planning view for any action? I’m always trying to completely match each next action with its hierarchy all the way up to my life’s purpose. That, along with trying to get my system to match my exact internal planning monologue (I want to do this, then this, then this) has really caused me a lot of friction.

I had one other idea: I could literally go as basic as a basic next action can be, because that forces the next part of the definition. For example, the long form of the task would be: “Trigger to initiate the process to move my body to the trash bin so I can take it to the curb.” That’s literally as far down as I can boil a next action, and then just take the clarifying section and use that for the next action: "Take it (the trash in the bin) to the curb. Ha! I’ve found a solid wall to brace myself against, you can’t get any clearer than that.

So then, the context would be: “Any situation in which I could start to move my body toward the trash bin so I can take it to the curb.” I’m not sure how to simplify that context yet, but I’ll think about it.

Then, instead of trying to define how all that moves up the hierarchy to life’s purpose, I’ll just stop there. Although I would really like to have the time to map everything all the way up each horizon, it’s an impossible task of I want to get anything done. Which is disappointing, because I wish I could do that and still have time to work.

Wow, long post. Anyway, thanks again! I hope to hear some more wisdom from you soon.

@DrJJWMac provided an excellent response. I’ll just add that the Natural Planning Model proposed by David Allen in the GTD book is really helpful for me. It gives me perspective, keeping me from getting goofily granular while still connecting to my larger goals and vision. PM me and I can send you one from his Web site and another worksheet I found elsewhere.

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A summary of my context list is given in this post. As noted, this list took me about two years to finalize. From a bottom-up ordering, …

  • consider: a first notice that actions may be needed
  • define: state the problem, question, goal, outcomes, …
  • research: collect any missing information
  • plan: put together the actions that will resolve the problem
  • do: carry out the actions
  • tidy up: review the results to that point
  • deliver: send out a report out on the project’s status
  • close: tie up any loose ends

On projects of significance, I use the note field to record this information succinctly

  • problem: what is the core problem or question?
  • approach: how will I go about solving it (in general)?
  • outcomes: what will I have (as a deliverable) at the end?

As a background, I am an engineer by training. Problem solving is my life’s blood (and sometimes my own private curse, but that is a longer story). I can expect that my context list will have limited appreciation outside comparable disciplines or mindsets. Also, I do not compile my context-map exhaustively for everything that I put in to OF. Some projects may for example have only three context actions: do, report, and close; do, tidy up, and report; propose, do, and close; … In this regard, the template of contexts serves me well to narrow my action list and prune redundant actions, e.g. why have this …

Paint Wall

  • set up ladder [do]
  • collect supplies [do]
  • climb ladder [do]
  • hang paint can [do]
  • review wall for missing spots [tidy up]

… when this is “cleaner” …

Paint Wall

  • paint the wall [do]
  • clean behind on any areas missed [tidy up]
  • put away the supplies [close]



You can also start here or here or … (last reference removed … copyright violation???)

For others, do a search for “natural planning model david allen”.


Ah, that is what I’ve been having a lot of trouble with recently! Things can be broken down forever and ever, and it’s hard to know when something is “sufficient” because I’m looking for hard line outside of myself to decide that, not my own judgment. “Do, tidy up, close” is a helpful setup for this. I’m having trouble because I’m focusing too much on the idea of getting specific with my next action, causing me to write things like: “This is a reminder to initiate the impulse to move your body to the location in which you can initiate the process to paint the wall.” My system is just a massive Zeno’s paradox…

Let’s be honest: what you and I sometimes call perfectionism is the masked dread of actually starting to do something.

There. I said it.

Now that we got that settled it becomes obvious that planning depth only needs to be as deep as enabling you and me to get the task done. That was the initial reason for starting to plan the task.

Off you go!


I think that’s definitely a factor, Mat. I know that, for me, sometimes I’m not planning on doing the task right away though. I’m simply trying to get enough granularity to make sure I see the reminder when I mean to see it. During the processing step, I may not be prepared to make the judgment call to just finish planning and go paint the wall. It’s only after processing is done that I can trust that choice. But if processing is never complete due to infinite task regression I fall into the choice between abandoning a half-done system, or sticking with it and not ever making it to the intuitive judgement phase for what to do next.

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I think both the goal and key to using a system like OmniFocus is to basically turn it into a ‘trusted system’ where you know that you can put things and forget about them until they become relevant.

However, since no system can read your mind, and few people have a life that is so well-organized and structured that everything happens like clockwork, the “Review” system is, in my opinion, critically important to the entire process.

The problem with computers is that I think many of us look to technology to be the magical, artificially intelligent solution that can just read our minds and bring up what we need, when we need it. I like to call that the ‘Star Trek’ dream of technology… the problem is that on Star Trek, the computers and actors just have good script writers, so of course the computers know what the characters want :P

Personally, I fell into that trap years ago, but ultimately I gave up on the ‘killer perfectionism’ of fine-tuning OmniFocus, accepting the fact that it would never be able to perfectly advise me of what I needed to do in every possible scenario. I settled for having it address about 60-80% of what I need, and then fell back on the manual, human review processes to basically act as the fall-back and catch the stuff I might otherwise miss.

My routine thus involves weekly and daily reviews. I dump everything into OmniFocus and if it’s more than a week out, I rarely even give it a second thought when I’m first entering it. When it comes time for my weekly review, I look at pretty much every project except for the very well-established and very linear ones (which are set to a longer review cycle – so they still come up, just less often). During that process, I’m effectively reminded of every task that has any possibility of needing to be done that week, along with a number of longer-term tasks that are on the horizon. From there, I can decide if I’m going to make any given task an action for that week as I go through them, and equally I can decide if some things are really just no longer relevant and simply need to be dropped off my list entirely.

I then rely heavily on flagged tasks and defer dates. Anything I plan on getting to during that week gets a flag, and if I don’t expect to deal with it until later in the week, I put a defer date on it for that date. In some cases, I’ll flag and defer into the next week if I know for certain something is relevant for a given date, but if it’s even slightly nebulous, I just leave it for my next weekly review, when I’ll see it again anyway.

I have a perspective I work from which I call “Hotlist” that includes al available flagged or due items, with due items sorted to the top. I’ve broken that further down into perspectives that focus on personal or work projects, so I can use those during “office hours” versus weekend and evening times. Again, there’s no automated magic to this – I just use the appropriate perspective for whichever ‘mode’ I’m in.

During my daily reviews, I check the Hotlist to see what’s up for the next day or so, adjusting as necessary if priorities or timeframes have changed (e.g. deferring something if I know I can’t get to it today, or unflagging it if it’s suddenly no longer important for this week). I then take care of processing anything in my Inbox, and then I might go through a few key contexts if I’m looking for more to do. This last step, however, depends entirely on how many items I have on my primary hotlist (e.g. due or flagged items). Since I’ve already established what’s important for the week during my weekly review, there’s no point in going looking for anything else until I’ve dealt with that more urgent stuff in one way or another.

At the end of the day, I find this review process is what really helps me "trust’ OmniFocus and know that whatever I’ve dumped in there won’t get lost in a black hole somewhere, while giving me the security to just “dump things in” and deal with them later.


Yeah, purest truth, review is the essential step in the system! Nice thing to note: deferring a flagged task hides it completely until the date, then makes it available in the important list, where it stays even after the defer date has passed on… Otherwise OF would put it back into task hell aka the db without global search ;-)


First, thank you guys for this awesome community. I should have joined sooner!

I think defer dates may be an excellent resource that I’m underutilizing. But I’ve always wondered, shouldn’t I not defer things that could be done and prioritize on the fly? I mean, two hours after deferring something a golden opportunity to do it might come along and I could miss it if I deffered it to next week. Then, of course, the project list is just too long to review though. I can’t make an intuitive judgment from 300 items.

One thing that is happening is that you have too many “active” projects. Whenever I get new projects or ideas, I create a project and immediately set the status to “On Hold.” I am not working on these new ideas/projects because i have to take care of my currently active projects.

The only lists/projects that I have active are Single Action Lists that have routine tasks (mostly administrative stuff) and another Single Actions List for each Area of Responsibility (Work Single Actions, Home Single Actions, Personal Single Actions). These are one-off tasks that don’t need a project (get a new light bulb at the hardware store).

Then I have up to 3 Big Rock projects in different folders in each folder. I have 3 Big Rock projects with an “Active” project status in my Home folder (big projects I want to work on at home). I have 3 Big Rock projects with an “Active” project status in my work folder (big projects that I want to work on at home). And so on. I’ll have 1-3 Active projects in each of my different folders. All of the other projects are set to “On Hold.”

Here is a sample of my Home folder.

As you can see, the only active items are my Home Actions, Home Routine, and two Big Rock projects - a Decluttering project, and a Pool House Renovation project. Other projects such as tiling the living room stairs, renovating the master bathroom, and securing house entry points are set to “On Hold.”

The decluttering project and poolhouse renovation project are big enough for me. I don’t need to activate any more projects because I already have my hands full with these two active projects. I won’t work on the other projects because I want to finish these two active projects before going to another project. I know that my capacity is limited. Having more than 3 Big Rock projects just dilutes my focus. I know my wife would kill me if I was spreading my efforts on different parts of the house and taking longer to complete anything. She would want me to finish the pool house renovations and the decluttering projects first before even thinking about the other Home Someday/Maybe projects that are set to “On Hold.”

I’m not worried about an “on hold” project getting lost. The secret is in the review process. For projects that I will work far into the future, I set the review cycle to once a month, two months, or three months. I know that I will see them eventually. I can set the review cycle to weekly if I am worried that I might miss an “opportunity.”

Don’t jump at every shiny object or shiny new project that comes your way. Just record it, put it on hold and it will be safely recorded and waiting for your next review date.

A lot of single actions don’t have to be worked on. I can just save those single tasks into my Home Someday/Maybe single action list, I might put “dream” stuff such as a new barbecue grill pit or a fancy new spa in there. I am not going to work on these dream tasks but I know it is entered into my Home Someday/Maybe list. At next week’s review, I’ll see those someday/maybe items and I’ll consider whether to work on it this week. Otherwise, I click “Mark as Reviewed” and forget about it until the next weekly review. It will show up at the next appointed review date.

Seriously, if you have 300 projects, how many projects are you really working on? Wouldn’t it be more efficient to complete 3 projects successfully in a week rather than have 300 projects that have been half-started or in various states of incompletion for months or years?

I would suggest choosing 3 Big Rock projects, focus your energy and time into completing them before moving on to the next 3 projects.

We can also tackle the next big question: out of the 300 projects, which ones are really important to you? Which ones can you delegate to someone else who has more time, more energy, more skill level, and better tools to accomplish a certain project? Which projects are still important to you? Start deleting projects that were once important but is no longer relevant to your life. Delete projects that will have little bang-for-the-buck. I’ll give an example of a project I recently deleted:

I was thinking of creating a project that would get lyrics to all of my favourite songs in my iTunes library. It sounded great to have song lyrics on my iPhone whenever i wanted it. I kept this project in Someday/Maybe for a whole year. But then I realised that whenever I listened to a song, I rarely cared to look at the lyrics. I just deleted the project. There was little reward for my efforts.

When I first started GTD. I felt great capturing all of these crazy ideas and projects. But I eventually overloaded myself with too many projects and went crazy under the burden of seeing a long, endless list of projects and tasks. After I learned about how to do a review, I started curating my content. I put everything on hold, deleted projects that have lost value, delegated projects to others who were better equipped to finish them, and choose 3 Big Rocks to work on.

Learning how to use project status (Active, On Hold, Completed, Dropped) will boost your results.

Life is about choosing to do what’s important to you.

Good luck.


[quote=“wilsonng, post:13, topic:12956”]
I was thinking of creating a project that would get lyrics to all of my favourite songs in my iTunes library. It sounded great to have song lyrics on my iPhone whenever i wanted it. I kept this project in Someday/Maybe for a whole year. But then I realised that whenever I listened to a song, I rarely cared to look at the lyrics. I just deleted the project. There was little reward for my efforts.[/quote]
Heh, that one is so very true, and I recently purged a half-dozen similar projects from my list while going through and reviewing stuff, including one about lyrics.

Letting go of the OCD about having things organized has been a boon to my productivity… As my available time goes down, so does my realistic desire to be bothered with stuff like this, and at the rate technology moves, who knows what format my iTunes library will be in or what other services will be available by the time I get around to that task :)

Some good ideas in general, however, and I could probably do to spend more time fleshing out and focusing on my “big 3” projects as well… While I’m not overwhelmed, a slightly tighter focus is never a bad thing, and if something is living on the back burner, it’s probably not a bad idea to make a conscious decision to put it there, rather than just letting it sit there by default. If nothing else, it adds a sense of control and direction to the process… Taking conscious action about stuff you know you aren’t going to do is just as great for peace of mind as tackling the stuff you do.


That’s rest advice, thanks! I guess I just want my system to keep me on top of everything, but I’m not keeping in mind my limitations.