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Removing structure to be more structured

My wife and I’s first children, twin boys, arrived about a month ago. As you might expect, their arrival has totally wrecked my routines and traditional “productivity”. In the past I’ve had a perpetually evolving system of using notebooks alongside digital tools like Things 3, Todoist, OmniFocus, etc.

I’ve been guilty of moving constantly between these digital tools for various reasons, basically just because it felt productive and exciting to design a new system. Of course these would work for a while and then need “replaced” again. The relationship between the todo list and the calendar has always been a contested one. In the past I’ve tried various common approaches:

Approach 1: Working entirely from todo lists without a calendar

This approach works reasonably well for me in small doses. Because I have Autism and some executive function issues because of that, I am comforted by having an explicit list of things to do and in which order.

My tendencies, though, can make these lists extremely long an overly detailed: At one point in time I had an index card in my bathroom which listed out my entire hygiene routine to make sure I completed it appropriately.

Approach 2: Maintaining todo lists with repeating calendar blocks

With this approach you still maintain todo lists but you instead also add blocks of time to your calendar during which you intend to work through the lists. For example, maybe you have a list of chores around the house that need doing so you batch them together and do them in a 30 minute block of time that repeats everyday.

In practice I’d use something like OmniFocus tags/contexts to create this hot lists on the fly. They might be location based “At home”, or effort based “5 minutes or less”, or even just thematic “family”.

I think this approach is definitely a step in the right direction over pure lists because it forces you to associate the things you want to do in life with the time you have available to do them. However, for me, this approach can become stressful if I don’t feel like I’m progressing in my lists or if external events break my routine (again, as Autistic I am very sensitive to unexpected changes) and cause me to get behind.

Latest Approach: How I’m getting things done in my new life

Soon after the babies arrived and I started to actually exit the sleep-deprived zombie phase of new parenthood, I realized that my systems from before were all busted: both literally and philosophically.

Literally, I had a huge mess. Repeating OmniFocus tasks had piled up, Due reminders were repeating so much iOS actually blocked additional notifications from the app, and emails were of course out of control.

But also philosophically, as I found myself churning through catching up my system and not really being present with my sons. If the idea of “productivity systems” is to get the important things done in your life, it was an obvious red flag that it was distracting me from my brand new sons, who are clearly one of the most important things in my life right now.

About a month later now, my system has developed into something like this:

I’ve actually stopped using apps like OmniFocus, Things, or Todoist. I’m not using any “todo” app: I am keeping lists of tasks related to projects I’m working on now (we are buying our first home, for example) in Bear.

For repeating tasks such as hygiene and domestic chores, I’ve grouped them blocks of time and added them as repeating events on my calendar with the lists in the description field of the event in Markdown format.

These have default times of day but I always end up moving them around inside the day, which detaches them from the recurrence rule and lets me make changes to just that event for that specific day. This gives me the benefit that I can check off the items in the description while keeping the future copies of the event in their default unchecked state.

For the most part, though, I have no specific goals for accomplishing tasks in specific time blocks. I have been creating repeating time blocks for the 2-3 projects I’m actively working on and just including a link to the Bear note inside the calendar event.

It’s a subtle distinction from Approach 2 above but here’s the best way I’ve come up with to explain how it’s different:

Instead of fitting a schedule to my tasks I’m fitting my tasks to my schedule.

The focus is on how I spend my time and not what I’m specifically doing with it. This seems a bit dangerous because without specific accomplishments in mind it could be easy to not make meaningful progress on anything. I’m finding, though, that the freedom from todo list tyranny is helping regulate my motivation and willpower, which is already so variable right now with the constantly changing new parent lifestyle.

Published 12 Jan 2019

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