Broken Promises & the Costs of a Trusted System

Broken Promises & the Costs of a Trusted System

Many systems and apps seem to promise everything, like guessing your motivations and prioritizing your next best thing to do.

But the implied promise readily breaks.

Here’s why and what you can do about it…


Every app, every system promises some sense of ease from decision.

Can I finally get things off of my mind?

We’d like to know:
– the best next thing to do is
– without thinking
– with my desires and wants of the moment taken into account
– in the perfect place and time
– optimized and ready for the tools at hand

To this end, we might study one pattern or another. *Getting Things Done*, *Franklin-Covey*, and if I may be so bold, Being Productive, and the like are good examples. Notion, Roam Research, Obsidian are various apps. Maybe AI is the answer to our prayers?

Any one of these can be quite useful. They’ve each helped me in my own ways.

Whether tool or methodology, we pick here and there, gradually creating some creature to follow us throughout the day. They work, they crash, some parts stick around, others don’t.

The Implied Promise

The trouble is that the implied promise that you won’t need to think is simply wrong.

The issue is seemingly trite. Well said by the GTD tenet, you need a “trusted system”. That means something you *genuinely believe* will bring to your attention those things you find meaningful, when and where they would be useful and to do so with clarity.

Genuine belief, however, requires your involvement.

Without it, trust simply does not form. Trust is not something you wish or hope for. It is something developed in time through direct experience.

And that requires time.

Time Spent Organizing

Organizing is a continued process, a flow across time. I am always in the work of fine-tuning, particularly as I work. My systems are in my mind whenever I find frustration, which is to say quite often.

As a result, it is difficult to give a definitive statement as to how much time I spend in it.

Currently, my digital tools, all having come under the evolutionary force of organizing, help me:

– Consider the Now and the Not Now (Pen & Paper – Waves of Focus
– Gather my thoughts (DEVONthink – Taking Smart Notes with DEVONthink
– Store and present my intentions (OmniFocus & OmniOutliner – Creating Flow with OmniFocus
– Organize my files (Hazel)
– Connect my files (Hookmark)
– Connect with my digital systems (Keyboard Maestro)
– Guide myself through time (Busycal and Due)
– Express myself quickly and consistently (TextExpander)

On a daily basis, I spend a few minutes with my pen and paper guide and OmniFocus, aligning and updating my interests of the day.

When I have had a batch of ideas sitting in DEVONthink’s Inbox, I spend some time that day and every day thereafter until cleared, attempting to connect them to where I feel they best belong.

That might take a few moments, or it may take hours strewn throughout the weeks, depending on whether the muse has decided to gently visit or drop bricks on my head.

I visit my calendar daily, scheduling and updating in the moment.

On Fridays, for about a half hour, I skim through the major branches of OmniFocus, looking for things that may be lost in the cracks.

On Sundays, I spend about five to ten minutes creating a new pen and paper guide. I really enjoy this.

And every day, I attempt to dive into something, be that in music, games, or the study of guiding of the mind. This is where I often discover and garden the seeds of some new project or path forward.

In this way, while there are certain parameters and timings through the week where I review and build my systems. But the core is that organizing is a continual attuning between self and world, a motif of practice that weaves itself in and throughout the day.

While some things can be measured, much of what has worth cannot.

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