Slipping through the cracks

On reducing my reliance on list keeping to help put first things first

For many years I struggled to do the small things.

Jess would ask me to grab something from the grocery store and I’d forget.

I’d have a small errand to do and I’d forget several days in a row.

I’ve always been more natural with the high level themes. But I struggle to keep life’s day-to-day details in the front of my mind.

In an effort to improve I started writing lists of these small, but important items.

Asana’s iPhone app provided the first measurable improvement in me being responsible on a daily-level. I’d write everything in there. Then when Google released Inbox in response to Mailbox’s email snoozing, with the added power of Reminders, I was all in.

For the past few years, this system has worked incredibly well. I can snooze items that aren’t urgent and keep important things on top of my mind without having to commit mental energy to keeping them top of mind.

This year though, I’ve slowly become aware of a feeling that my list-keeping has allowed many small (and arguably non-critical) tasks to consume my days. To the point where I’ve lost that sense of freedom and serendipity because my days are spoken for before I even wake up.

The beauty of a list is nothing slips through the cracks. But the prison of a list is it doesn’t let anything slip through the cracks.

I’m starting to attune myself to the reality that it’s okay that certain things never get done (or at a minimum, get done as the need or opportunity naturally arises).

Too often items in my Inbox get snoozed for weeks or months. Every time resurfacing a reminder of that thing I don’t feel like doing and the guilt that comes from having not done it.

On top of this, this year has been full-on, and there’s been good portions of the year where I’ve been drowning in my Inbox full of tasks and to-do’s and reminders of things that need to be taken care of. Things that I haven’t had time to do, or deep down don’t want to do.

In short, I feel like my list keeping is wearing me out.

So these past two weeks at home I’ve been experimenting with not writing certain types of things down — in an attempt to both let myself remember when I do and leave space for me to follow my inspiration in the moment.

I’ve been mostly leaving household items off the list. Things like “laundry”, “check the mail”, “water plants”, “litter box”.

What’s interesting is that despite all of those things getting done these past two weeks, I’ve felt so much lighter each day not having a list of “have to do’s” weighing me down.

I think the key change is the order I’m doing things.

The order we do things matters.

I became very aware of this during this past trip to Barcelona and Lisbon. Having most of the day to do what we wanted for ourselves before sitting down to start working felt so much more fulfilling. I felt like I was able to do a bunch of stuff “for me” before having to do a bunch of stuff “for someone else.” This is the exact opposite of how the normal 9-5 schedule at home operates. You give your first and best to “someone else” and “you” get whatever’s left after that.

The same feeling has been true in relation to my list keeping since coming home. Instead of doing a bunch of stuff “for the list” first, and then only having the leftovers for myself, I’ve naturally swapped the order to match how things were in Europe.

The order matters because you only have a limited and finite supply of “first and best” time, energy, creativity, focus, etc. If you spend those resources on low value items, you have little left for the things that matter most.

And for me, my compulsion when given a list, is to knock it out so I don’t have it hanging over me and can then get on to the things I truly want to do, or are truly most important.*

Keeping a shorter list is helping me put first things first. And I’m finding the best way to lighten the load is to let some of those last things slip through the cracks.

* I wonder if this pattern’s origin traces back to my academic life, where I was (understandably) required to finish my homework before doing anything else.

🤝 Stay in touch

I send an email several times a year with a handful of the most interesting things I’ve written or uncovered at home, abroad, and on the web.

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