OmniFocus

Dashes

January 6, 2022

I find that working in dashes is a spectacular way to make incremental progress on something. My favorite these days is a ~40-minute dash using a large sand timer. My dashes always run a few minutes over, and then accounting for time after the dash—to deal with whatever has come up—these dashes effectively consume an hour of my time. Reading, listening to podcasts I’ve curated for myself, writing, or working on outreach to invite people onto a podcast show, are all things which will never be finished. They’re perfect never-ending projects to be tackled in dashes.

I’ve been using health tracking grids, which I keep directly in my personal journals, and a tasks and project management program called OmniFocus, for over a decade. I have a long running drive to track small steps that lead to big changes or big goals. For a specific type of step, or task if you prefer, this has consistently failed miserably.

The problem is that progress on such projects doesn’t have to be do-it-every-day perfect. I simply need to do it often enough. If I have a row in my health grid, it stresses me out if I go days without ticking it off. The same happens in my tasks and projects software; A recurring to-do item for “reading” just sits there with an aging “was due on” date, adding stress. When January rolled around this year, I removed all my forever-projects from both my health tracking grid, and my tasks and projects software. Perfection, in those two systems, is now something that I can actually achieve.

Now, what to do with the never-ending projects? I spent some time whipping up a spreadsheet of “don’t break the chain” style tracking. (This is not a new idea, I’m aware.) Here are three sheets, for three different groupings of never-ending projects: “Writing” for three different publication places; “Community Building” efforts in three different contexts; and “Reading/Listening” in three different mediums. (On one, I was drawing empty squares, but decided simple dots were fine for “didn’t do.”) I like the filled in panache of which ones are done… they are really done.

Most days, I set myself a rough list of tasks with any things at specific times marked as well, in a small notebook. The tiny size of the notebook helps remind me to not plan too much for each day. It’s an eternal struggle of course. I do not look at these sheets when I’m planning a day. I know what needs to be done—all 9 of these dashes are never-ending projects which I want to see move forward.

“I need to write some blog posts today…” goes on my day’s plan, and that’s going to be one dash, and blog writing is often much longer than 40-minutes. “I’m in an accountability session that’s part of Movers Mindset, and I’m being held accountable to write every day for that…” goes on my day’s plan as a dash. And some other things get added to my day’s plan. Then as my day goes on, I might spontaneously do some reading, or go for a walk and listen to some podcasts. At the end of the day, (or the next morning,) I pick up these sheets from where they site out of my sight and I fill the day in.

Several lessons are being taught me. 9 freakin’ dashes in a day is literally not possible; the most I’ve done is 5 so far. 2+ is the average, and 3 feels like it could really work. It’s interesting that 3 is the number, right? How often do we hear to pick no more than 3 “big rocks” to put into each day? It’s also really clear where my commitment actually falls; That “plan/outline” dash is not just a dash. I start by planning within an enormous outline document which contains all my plans for two entirely different and very large projects. And then I often spend an hour or three working on things from that plan. I should be able to get through that entire plan, and then retire that “project” from the dashes tracking.

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Time spent organizing my time

September 6, 2020

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.

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Tis the season

December 13, 2019

I like paying for my software when I’m buying it from a company that’s responsive, fast and focused. I like being the customer (as opposed to a social network, where I’m the product). I spend most of my day working with tools that weren’t even in science fiction novels twenty-five years ago, and the money I spend on software is a bargain–doing this work without it is impossible.

~ Seth Godin from, https://seths.blog/2018/06/on-paying-for-software/

Tis the season… to talk about paying for the things we get value from. Last year Seth wrote that great gem about software and I whole-heartedly agree.

Here’s a short list of a few pieces of software which I gleefully pay for, without which everything I do would be vastly more difficult or outright impossible: Hover, BBEdit, Hindenburg, Overcast, Reeder, Feedbin, Tower, Transmit, OmniFocus, OmniOutliner, iaWriter, Discourse, Basecamp and Front.

As a bonus round, here’s a short list of a few online services or publications which I also gleefully contribute to, because they provide me with magnificent information that makes my world a better place: Brain Pickings, Müvmag, PodNews, Once is Never, and WikiPedia.

My challenge to you for the holiday season: Post your own lists somewhere public, and share the love for the software and services that make your life better throughout the year!

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