When Your Planner Disrupts

Noticing that the way I maintain my daily planner was causing me distraction, I recently realized that a major problem was that I was attempting to use the same document to simultaneously track what venture capitalist Paul Graham might call the maker's and the manager's aspects of my schedule, or Cal Newport (author of Deep Work) might call deep and shallow work, or Alex Epstein might call what-thinking and how-thinking. (These categories do not completely overlap, but they together indicate that different kinds of work require different kinds of planning.)

What is missing, here? (Image by Austin Distel, via Unsplash, license.)

My own terms for coming to grips with the time aspect of my problem are scaffolding and space. The former type of planner item includes things like phone calls, errands, small tasks, and scheduling constraints like appointments. The latter includes time for such deep work as research, mulling, and writing. I was finding the format of the planner, while ideal for helping me navigate the non-deep part of the day, was hindering me during times I wanted to do deeper work, and this was even after I had started planning that in advance in order to avoid decision fatigue. Here is my initial stab at what was going wrong, from a journal entry:

The document I have been calling my Planner is an unholy (and demoralizing) combination of scheduler and to-do list. I feel very limited when I look at it during creative/work time because of all the crap hanging over me AND (I just realized in words): Nothing creative or productive [in terms of deep work] is listed. [format edits]

The last sentence isn't completely accurate: I'd have things like "research "X or "work on a column for an hour," but these were jumbled in as bullet points of the same order as "Take kids to gymnastics," or "Call about hurricane deductible."

There are at least three things wrong with this: (1) I start out a deep work session with unnecessary reminders of things I am free to set aside; (2) I didn't necessarily have any kind of breakdown of the tasks on hand; and (3) The inflexible format of the planner wasn't conducive to note-taking or brain-storming -- unless I already had a dedicated place for that. The last two are related in the sense that sometimes there is no way to know exactly how to proceed. But that should be noted, if it is true, I think. (This both sets a standing order for the subconscious and serves as a reminder on the day.)

But the most glaring problem, I see in retrospect, is that the planner wasn't capturing creative, longer-term goals.

All that said, my planner wasn't worthless: That kind of planner helps me determine and remember the structure of my day, like scaffolding. But it was ill-suited to guiding me during my deep work during the spaces of time I allotted for it.

Recalling, possibly from Deep Work, that Newport would just sketch out a plan for his deep work in no specific format, I decided to try using two types of planners. The old planner is now strictly for "scaffolding" and the new for "space." The new planner does not have bullet points and more closely resembles a journal. The format for a given day varies, depending on what I want to do, with only the following usual formatting:

1. Date: There is a date at the start of a day's entries.
2. Goal Listing: There is link to the section of the other planner where I list goals and time blocks for the day.
3. Block Header: At the start of a block of deep work, I briefly re-state my goal.
4. Notes: If there is not a separate place for notes on whatever it I am working on, notes related to my work go next. This can be as much as a few short paragraphs or as little as a brief sentence summarizing my progress. (If I can't work on something, it's a scheduling problem and I make an entry in the scaffolding planner.) I usually note the time I start a block.
5. Block Footer: I always put down the time a given block ends and make sure I have some form of notification.

This is a new habit and a work in progress, but I have already noticed I look forward to planning each day. I also feel freer than I did before since I don't look at the "scaffolding" quite so much.

In the interest of getting more ideas about planning deep/maker's work, I did a search on Cal Newport's productivity blog yesterday, and think the following three "deep habits" entries will be worth consulting as I get used to working this way: Plan Your Week in Advance, Three Recent Daily Plans, and How a Big City Lawyer Uses Weekly Planning to Accomplish More in 45 Hours Than Most Could Accomplish in 100. From the first:

On Monday mornings I plan the upcoming work week. I capture this plan in an e-mail and send it to myself so that I will be sure to see it and have access to it daily. (See the snapshot above of some recent plans in my inbox.)

This planning can take a long time; almost always longer than an hour. But the return on investment is phenomenal. To visualize your whole week at once allows you to spread out, batch, and prioritize work in a manner that significantly increases what you accomplish and goes a long way toward eliminating work pile-ups and late nights (the latter being crucial if you practice fixed-schedule productivity).

There is no best format for creating a weekly plan. In fact, I've found it's crucial to embrace flexibility. The style or format of your plan should match the challenges of the specific week ahead. (Indeed, attempting to force some format to your plan can reduce the probability you maintain the habit.) [links in original]

Newport's first sentence gave me an actionable idea regarding planning the week: That, too, requires distinguishing between the scaffolding and the space. I had been attempting to plan my next week each Friday afternoon, but often finding myself not feeling very energetic. So I'm splitting that up, too: I will lay out the scaffolding on Friday, and briefly consider what deep work I want to do the next week. But then, I will plan in more detail on Monday morning.

-- CAV