Here’s what I learned from 20 months of planning…

Last week marks the first time I’ve ever reached the end of any planner.

(I also ran out of ink - also a first. I’ve usually lost my pen well before that ever happens!)

I evolved and learned a lot in the last 20 months since formalizing a planning habit.

THE GOOD

I started with Bullet Journaling. 

I found it incredibly adaptable. It let me make up sheets as I went along - from jotting thoughts to taking notes at meetings. The indexing system helped me keep track of it all (even though I started getting lax at going back and actually indexing pages).

It helped me accomplish tasks at different rates. Early on in my planning journey, I used the metaphor of compound interest towards long-term projects. If I was consistent about doing them, it didn’t matter if I only did a little bit a week – the work surprisingly added up fast. My tendency is to work linearly, attending to tasks that need doing now. But working in 10 to 40 minute sets per week helped me finish big tasks like a grant proposal, a fellowship application, and a book proposal. I was even able to finish a book for a club discussion without panicking and cramming the reading all at the last minute (which has definitely been my M.O. in the past). 

It helped me develop long-term strategy. I did this by focusing on the low end of output and time (planned mediocrity). Overestimating the time needed for a task better equipped me to see where I’d be the next week instead of hoping to be there. The added psychological benefit was that I tended to exceed expectations.

A planning habit also worked wonders with off-time. “Weekend menus,” which I’ve used in the past, came back in a more consistent manner, and I felt more energized, attended more organizations, and explored more of my city as a result. 

I created flowcharts for standardized tasks, and also learned how to plan a trip. Although I’ve traveled a lot, I’ve always been reliant on happenstance or Lydia’s amazing planning skills. I planned road trips, national travel, and even city exploration of different neighborhoods. It’s developed into a replicable system that gave me a sense of competency, which really can’t be emphasized enough.

Lastly, I created a robust planning metric. In the past I’ve found that a solid assessment of a behavior allows me to try different techniques to see what works to improve scores. This worked wonders for my sleep, and this simple planning index showed me where I needed improvement on a week-to-week basis. I intend to publish it as a post of its own, but here I’ll reveal that it assesses the number and types of tasks, emotional calmness, adaptation ability, and time estimation accuracy. It’s a work in progress, but I’m still quite proud of it as a practical diagnostic tool.

But not everything worked so well

THE BAD

Lydia suggested separating days to focus on specific tasks - like “pitching Mondays” or “social media Wednesdays”. This didn’t quite stick. Nor did attempting a project-oriented graph, like what Brandon Sanderson does for his work. 

Which is unfortunate - in one article Holly Lisle mentions how she can project with accuracy how long her books will take to write. That’s something I envy, but is pretty difficult without knowing for sure how long specific tasks (like creative ones, or editing) take. It’s all the more frustrating because in many instances jumbling tasks up is the most efficient way to do them, even if it’s hard to time.

For example, after I finish a first draft, it’s better to take a break and do something else before editing. You gain some distance, and are able to view your writing with fresh eyes. But it’s more difficult to time a project when you’re threading it with other work.

So I bought Timeular - a dice-like gadget that times various projects depending on how you hold it. Timular will show you how long Task A takes overall even if you’re interrupting it constantly with Tasks B and C.

However, I had a problem using it because I wanted to somehow divide tasks according to their behavioral efficacy. If Task A is made up of tiny tasks of editing and creativity, then those need to be treated separately and are best planned out to match my energy levels. Creative tasks are best done when tired, analytic tasks like editing are better done when alert.

This issue of syncing up broken up projects and smaller behavioral tasks is a huge mess that I’m still working on.

Assigning tasks was really problematic because there ended up being three different things to take care of: Whether I was distracted or not, whether it was early or late in the day, and how to fit it all into days of the week. 

Furthermore some tasks were contingent on other tasks, others were emotionally draining, others required help, etc.

I was also bad at looking at the big picture. Looking over this notebook, I can see how I still lack a true method of long term strategy. Circling back to hone in average task times almost never happened (other than a weekly post mortem to see how I did on the planning metric). And I also didn’t have a set time to go back over to-do items, causing a lot of tasks and reminders to get lost in the cracks.

FUTURE IMPROVEMENTS

Long term strategy and emotional tricks are two standouts I need to work on. The idea of somehow becoming utterly calm and unflappable, while at the same time getting a lot done on multiple types and rates of projects, is incredibly appealing.

I’m also looking into nonlinear planning, an odd subsection in artificial intelligence. It’s used to create programs that partially solve problems that are contingent on solutions from other partial solved problems. The more I delve into it, the more I realize just how often this becomes a problem in people’s day-to-day planning, but virtually no one seems to talk about it with any rigor.

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My inability to plan has adversely effected my growth in all sorts of arenas. But on the whole, creating and taking my planning metric forced me to figure out basic things I had never thought about - like my average work load. Systematically progressing and strategizing like this is a weird feeling, like finishing an entire planner. And it can only get better.