Time spent organizing my time

Something organized people don’t often talk about is how much time they spend organizing their time.

~ Cal Newport from, https://www.calnewport.com/blog/2015/11/03/spend-more-time-managing-your-time/

Guilty as charged, Your Honor! So today, something a little lighter than usual—I think?—with a few snapshots of how much time I spend organizing my time.

It is an exceedingly rare morning that I don’t spend about half an hour planning out the day. This little block of time begins with “surfacing:” Ducking into all the many online mediums where I am present, and—this is very hard—not engaging, but skimming over things to see what rises to a level of getting my attention today. Many productivity sources and guides suggest doing this at night, at the end of your day, but that does not work for me.

Every Monday I take an “administrative day”—the entire day. I stuff the day full of all the random things of life. Any errands to run, laundry, lawn mowing if I can, bookkeeping (literal banking and accounting and such). I do my best to resist doing any real work. I do anything like changing the bed linen, or high dusting the house, or stacking firewood, or changing a flat tire on my bike, …anything that I would consider “not important” …except of course if I never got around to doing it, then it’s a critical disaster …that’s “administrative day” stuff. This isn’t exactly time spent on organizing, but still.

I use sophisticated planning/project-tracking software, called OmniFocus, to manage a lot of stuff. (Things from recurring daily things, to true projects that have many steps and milestones and due dates.) Every two weeks—on an Admin Day!—I spend about an hour just going through every nook and cranny of my OmniFocus. (If you’ve read Getting Things Done, this is part of the review process.) I tend to ruthlessly delete stuff in an effort to combat my incessant tendency to take new things on.

At least once a month—again, on an Admin Day—I do the same sort of “look through every nook and cranny” review of the Basecamp system that is used for one of the companies I’m part of. Sometimes I can do that in 5 minutes, sometimes I’ll spend hours on it.

At the least organized end of the spectrum, (yes, my time spent managing my time comes in a spectrum of how organized it is,) I often—maybe twice per month this happens—will go off, (as in “off the deep end,”) and outline some project that I’m considering doing. I’ll whip out my favorite outliner, OmniOutliner, and do a brain dump of some project. This can take from 5 minutes to an hour or more depending on what I’m thinking about. Quite often, I’ll then simply set aside some awesome idea that I don’t have the time to execute, or the resources to have it done under my direction. I used to think this was wasted time, but it is the only way I can get things off my mind: When it pops up later, I either think, “I already did all the thinking,” or I go back to the outline and tinker some more. (What remains, forever, is just to squash the recurring lizard-brain fear of missing out by not executing the project.)

So let’s see, how much time is all of that combined? I’m awake 16 hours a day, but realistically, only half that time could ever be used to some specific end. So 8 hours a day of “self-directable life”. 1 out of 7 days is an Admin Day… 1/7 ~ 0.1428… The rest of that stuff might—maaaaaaybe, but probably not—eat a second day’s worth of each week . . . 2/7 ~ 0.2857…

So in response to how much time do I spend managing my time? I’ll say:

15 to 30% of my entire available life.


Start where you are

If you’re trying to get to the beautiful lake or beach and you’re caught in the weeds, ignoring the weeds and their constraints will produce nothing but desperation and angst. You first need to know what weeds you’re in, and how to get unhooked from them.

~ David Allen from, https://gettingthingsdone.com/2018/06/starting-with-where-you-are-not-where-you-should-be/

Of course this insight is blindingly obvious once you see it.

…and I distinctly remember what it was like when I hadn’t yet seen it. I can’t quite put my finger on an exact year, but I remember a feeling—or rather a few feelings and things which kept happening to me:

I was often late.
I was often tired.
I was often bored
…and then suddenly realized I’d forgotten to do something that I had felt was important.


Closed loops

The point of life is not to get things done. But life is better if you are able—at your own pace, if and when you want—to get things done.

Aside: In addition, other people will like you if you are also consistent and reliable.

The point of reviewing what I’ve captured is two-fold. Get everything done, (some of which I may have freshly captured yesterday.) But also to not do things. Yes, it’s delightful to finish something; it’s delightful to close a loop. But it’s also delightful to simply not do something. I have countless ideas, and the vast majority of them get captured… and then summarily deleted to be not done.


Open loops

Jot down every loop that opens; whether it comes via email, or a phone call, or a Zoom meeting, or Slack. Because these loops might emerge rapidly, use a minimalist tool with incredibly low friction. I recommended a simple plain text file on your computer in which you can record incoming obligations at the speed of typing (a strategy I elaborate in this vintage post).

Then, at the beginning of each day, before the next onslaught begins, process these tasks into your permanent system. In doing so, as David Allen recommends, clarify them: what exactly is the “next action” this task requires? Stare at this collection before getting started with your work.

~ Cal Newport from, https://www.calnewport.com/blog/2020/07/23/on-confronting-the-productivity-dragon-take-2/

This two part process is the backbone of how I get things done. When I find I have too many ideas rattling in my head it’s time to do a bunch of “capture.” One’s mind is for having ideas not for holding them. I prefer to write things down rather than using a digital device. Yes, my phone [at least] is very often at hand—but I’m a digital import, not a native, so thumb-typing is torture.

Everyone agrees that capturing everything—whether digital or analog, notes, meeting minutes, thoughts, doodles, lists, everything… Capturing everything is important and useful.

But almost everyone has not fully apprehended that second part: Process that collection from yesterday. Every day review all the “captured” stuff and brutally assess it. Can I just ignore it/cross it off as done? Can I put that onto some other list (groceries, errands, etc.)? Why did I capture this? …is it a dream, a flaming urgency, something I want to think more about?


Mindful communication

With few exceptions, e-mail use arose organically within organizations, with little thought applied to how digital communication might best serve the relevant objectives.

~ Cal Newport from, https://www.calnewport.com/blog/2015/06/18/the-e-mail-productivity-curve/

As usual, this is an interesting article from Newport. He proposes a productivity curve for email—how productive we are without, with-some, with-more, with-too-much—which explains perfectly why some people love email and some people hate it.

The key point about email is to use it intentionally. Not simply one’s own use; not simply, “I only check my email twice a day,” or, “I’m always at ‘inbox zero.'” The key is to deploy email wisely, in a way which increases productivity of a team, (family, community, whatever.) If adding email into the mix is going to increase productivity, then do so. Then zoom out and look at all your other communication tools, and perform the same calculus. Email is simply one example of a tool which initially [hopefully] increases productivity, but too-soon becomes a detriment.



These distractions aren’t just unproductive, they’re anti-productive. They create more work than they replace.

~ Mark Manson from, https://markmanson.net/attention-diet

I wish I had learned much sooner the idea that distractions aren’t just wasting the time spent on the distraction, but are in fact decreasing the value of the time I do try to spend on anything focused and productive. Alas, it took me decades of experimenting to deeply understand it for myself before I could truly learn the lesson. Manson’s article is, as usual, irreverent and explicit—but it has some terrific points in it about how to go about crafting an attention “diet” to take back your mind.

My mind does need a lot of down-time and relaxation. But none of that looks like distraction. I deeply love sitting down to some great science-fiction movie with popcorn. I also deeply love me some burly physical work where my mind can press the “body: do things” button and then wander out of the control room for a snooze on the terrace. (I imagine Homer Simpson’s sipping-bird left in the control room; but mine’s pressing the, “continue hard labor,” button rather than his nuclear reactor alarm reset.)



My touch-phrase for 2019 was, “no.” In terms of self-imposed stress and crippling depression, 2019 was the worst year ever; I’ve more than 10 years of journals and I’ve checked. 2018 was bad, but 2019—the year I set out specifically to reduce the problems—was definitely and significantly worse than 2018.

I remain convinced that it is not possible to optimize one’s way out of burn-out. If I have 500 things I want to get done and I’m burnt-out, the solution is to reduce the number of things, not get better at getting things done. I’m speaking from personal experience, not from theory.

2020 has to be the year of getting less done.

In 2019, the “no” touch-phrase was meant to guide me to developing the habit of saying no to things coming towards me. A huge amount of ideas and opportunities come at me, and I’ve gotten much better at saying, “no.” (I’m not quite ready to say I’ve gotten “good” at it; but I’ve definitely gotten better.) I’ve gotten better at evaluating Big Asks from the world, and saying, “no.” A textbook example of that is people/groups which reach out to me, asking for my input or participation.

“No, I do not have the time to do that well.”

“No, I cannot to do that the way it deserves to be done.”

…and so on. Note particularly the absence of the societal lubrication, (a.k.a., the usual lie,) “I’m sorry, but…” Because, I’m not sorry. I’m defending myself, and I’ve reached the point where if my candid, timely, and honest response feels like a wack on the head… Bummer. Life’s hard; get a helmet.

2020 has to be the year of getting less done.

In a previous post I mentioned the idea of leverage; positing that I should focus on asking myself, “how much leverage does this opportunity afford me?” This still doesn’t feel quite the right fit for 2020 because leverage per se isn’t a value I’m interested in maximizing.

So that leaves me where?

2020 has to be the year of getting less done.

GLD — Get less done.

Maybe that’s the touch-phrase for 2020?


Some method for the trivial stuff

Here’s a problem I’ve faced recently: my obsessive focus on a small number of important project causes me to fall behind on the annoying little administrative stuff that pops up on a daily basis. I’m not talking about the regularly occurring minutia, like cleaning my apartment or working out: these can be easily handled with an autopilot schedule. I am referring, instead, to the random, unexpected productivity lint that regularly clogs my inbox and emanates a powerful aura of procrastination-inducing annoyance.

~ Cal Newport, from https://www.calnewport.com/blog/2008/11/18/the-stable-mucking-method-a-freestyle-approach-to-keeping-the-annoying-little-stuff-under-control/

The important point is that you have some intentional way of keeping up with administrative tasks. If you don’t, these little thorns will pile up until everywhere you look you find sources of stress. Or worse, to avoid the stress, you stop looking.

Newport’s post describes one method—one which I don’t personally use—and links to another post describing another method. The two posts give a good overview of the problem he’s trying to solve, and some thought-provoking ways of trying to tackle it.


Sand through the hour-glass

I mentioned recently that I sometimes use a cheap little sand timer when I want to know when to stop, but don’t want to be directly interrupted by beeps or alerts. The sand runs out quietly. At some point later, I notice the time is up and I bring the work to a stop.

Except when the sand timer gets stuck. My half-hour timer—just that one—every once in a while, stops dropping sand. It’s a pretty teeny stream of falling sand that I can easily miss at a glance. So it’s not at all obvious if it stops. I get into the flow of work. I’m thinking, “yeup, in the flow state.” I’m tearing along, confident that my little sand timer will quietly let me know when to stop.

…and like two hours later I notice the room is getting cold because I haven’t fed the wood stove. Wait wat. *taps sand timer* oh.

I can’t decide if this is good or bad. It’s like deep work roulette. I think I’m going to do a half-hour dash, but maybe I’m going down the rabbit hole. I could easily replace the cheap little sand timer, but I like the randomness of it. The analog-ness of it. Not only is its time keeping approximate, but sometimes it’s totally not keeping time.

Too much planning and structure kills spontaneity.


You can’t fool your mind

You can’t fool your mind.  It’s an expert on your current personal management system, and it knows whether you can be trusted to look at what you need to at the appropriate time.  It knows if you’ve decided what the next action should be. And it knows if there is a reminder of that action placed somewhere you will actually look, when you could possibly take that action. If you have not done any of that, your mind won’t let it go. It can’t. It will endlessly keep trying to remind you of what to remember. The mind is a loyal and dedicated servant, but it needs to be given the jobs it does well–not the ones that it mismanages.

~ David Allen, from Ready for Anything

…and yet I try all the time. Fortunately I’ve gotten much better at capturing my thoughts.

The important part, the hard part—one might even say, “the trick”—is to have regular and sufficient time to review all the things I’ve captured. Do I really want to read that book that piqued my interest? Do I really want to try that new recipe I found? Do I really want to go to the trouble of adding that new electric outlet in the dining room?

I see too many people with no way of capturing their thoughts, and I see very few people who have a habit of regularly assessing what they want to be doing.