Living Personal Systems Pt. 2: The Intentional Years

How I developed my principles and the systems that supported them

Original art

Part of a series on my personal systems:

1. Foundations of My Living Personal Systems

2. The Intentional Years ← you are here

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Towards the end of high school I began following a set of self-improving personal systems. In the five or six years that followed, I poured perhaps 1,000+ hours and hundreds of written pages into the endeavor, producing an intricate system of interlinked intentions and practices, all formed around a set of core principles. Today’s post continues the story and describes that interlinked system’s workings.

The most fundamental motivating principle of my early personal systems was the following:

“It’s worth knowing what you want to do and what kind of person you want to be.”

Over time, my systems provided me with that kind of knowledge across many aspects of life. I had routines and plans for each day, goals or “modes” for each season, and most importantly, a set of overarching principles to guide my actions.

We can call the whole set of routines, plans, and principles my “intentions.” At my systems’ core was a set of reflection routines which compelled me to describe, maintain, and ultimately to manifest these intentions as best I could.

The core reflection routines

I had two core reflection routines: a nightly journalling session and a weekly review. These were codified in a document called “Constitution” which lived in my digital notes and was the entry point to the rest of my systems.

The nightly journaling sessions started as unstructured free-writes. Each night I wrote about what was going on in my life and about ideas for upgrades I might make to my systems, such as: “I’d like to set up principles for myself that I can reference,” or, “I’d like to write down what I’m grateful for every day.”

Then, during my weekly reviews I read through last week’s journal entries and made updates to my digital notes. In part my goal was to integrate the week’s ideas into my systems as appropriate, but I also allowed myself to make additional changes, informed by the zoomed-out reflective standpoint that the weekly review provided.

These two core routines maintained and built upon themselves. For example, during one weekly review I read in my journal that “I’d like to set up principles for myself that I can reference.” So, I set forth to manifest that. I created a digital note titled “Principles” and updated my Constitution in two places to reflect the following: that during nightly journaling I should prompt myself to write about learnings that are relevant to my principles, and that during weekly review I should modify my principles based on the learnings collected in the prior week.

My goal for any described routine was for it to become a habit, and for that habit to effectively accomplish the routine’s purpose, and for the entire story of the routine/habit and its purpose to be well-described within my system’s Constitution. To achieve that state of systematic integrity I knew I had to regularly “give the system love,” meaning, to apply steady creative energy towards the improvement of each aspect of the system and towards the system’s overall coherence.

I also believed strongly that my systems would work best if I could genuinely commit to following my stated intentions, so I did my best to maintain that commitment. Doing so gave my systems the power to adapt and mature by their own rules.

Factored journaling for nightly reflection

Over time my journaling routine evolved, and pretty soon I was doing the following: each night I’d proceed through a series of prompts represented by the acronym TAIL: “Thankfuls”, “Accomplishments”, “Improvements”, and “Laters”. In order, I wrote about:

1. (T) What I was thankful for - in my relationships, in the world around me, and in myself

2. (A) What I accomplished that day, especially in light of my principles

3. (I) Ways that I might improve myself and/or my systems - this section would directly feed into my Principles document and others

4. (L) What I needed or wanted to do the next day

And finally I’d put a placeholder for recording dreams in the morning.

This system served both my immediate goals of integrity + calmness + gratitude + self-direction, and my long-term goals of systematic self-understanding and improvement.

Principles and their synthesis

“Reflection” (Trees and laptop screen)

Over years of weekly reviews I read every word of my daily journal entries, integrating my scrawled thoughts into a growing body of digital notes. The most important digital notes were those relating to my principles.

At first, my principles were a single document: a list of eight to ten sentences, like this:

Be a confident role model.

Together my principles made up a concise description of the kind of person I wished to be and the kind of life I wished to live, and I intended for my actions and my systems to serve them.

Once my principles document was set up, I built a queue to aid in the principle-synthesis process. During weekly review time I would copy my daily “Improvements” notes into this queue, and in time I would process each item in the queue, considering whether it might call for a modification to my principles or perhaps to some downstream system.

Eventually I realized that my true intentions, and even the subset of my intentions that I wished to write about, far exceeded what could be conveyed in these brief sentences. To give my intentions more space I started a new document titled “Principles: Full Considerations,” which grew to include short essays under each principle. Here’s an example (note: this is a shorter one):

Be a confident role model.
A successful role model has many traits: not only does he act in a positive manner and go about life in a way that benefits everyone, he also must be confident in his ability to teach, and willing to put himself in the public view.

I must start by understanding that people look up to me already and will emulate me if I am willing to make visible my thoughts or actions. I must be confident enough in my unique ways to put them on display, and I must display them confidently.

I must be the first to spring to action when a situation requires it, being guided by what is the right thing to do and not what others think. Don’t use “I don’t know” as a crutch.

As to my role? Following my other principles is enough to define my role as it pertains to being a role model. An additional note is to act respectfully in public settings, especially on the internet, and to show the best sides of myself to every single person I meet. Remember: I have the power to define the energy in any setting.

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To describe the full circle of principle synthesis: during nightly journaling I wrote about specific ways to improve, sometimes targeting my writings towards a particular principle and sometimes writing in a more free and uncategorized way. Then during weekly review I moved these thoughts into my queue for principles. Later I would integrate these thoughts into some appropriate section in my full-considerations doc, or, in rare cases, mint a new principle. In the end I had a well-adapted set of about ten principles with accompanying essays that integrated thousands of days of reflections.

The challenge of systematically realizing principles

Of course I knew that merely writing down intentions wouldn’t make them a reality, so I was constantly devising new schemes to become the kind of person my principles described. That endeavor was, of course, the most difficult part of the whole system, and I remained unsatisfied with my attempts to the end. But I tried many schemes and I liked some of them.

At first I would literally carry my principles in my pocket. Then at some point I created a new document called “Principles - Actionable Ideas” which described a protocol I could follow at any time in order to ground myself and direct myself towards positive action. Funny enough, the protocol started with a reality check, then branched one way or another depending on whether I was dreaming (I was practicing lucid-dreaming at the time).

But with that protocol there was still something incomplete - how would the full extent of my intentions cash out into reality? So I kept iterating. The next innovation was a “principle of the week.” During weekly review I’d choose whatever felt like the most relevant principle, then throughout the following week would direct my focus towards that principle by various methods. I also set up “seasonal modes,” which, like principles, represented intended ways of being, but were more closely adapted to my present circumstances.

I felt positive about these various attempts at principle implementation, but I remained unsatisfied, and despite my diligence things seemed to slip through the cracks. I loved my routines and thought that they brought me great benefit but I did not believe I had created the perfectly self-regulating system of guidance that I wished to create.

Auxiliary systems

While my main focus was towards the flourishing of my principles, I also regularly attended to a number of other systems and their written counterparts. The rest of my systems were ostensibly downstream of my principles, and I wished to make the links between each system and its motivating principles explicit, but I often struggled to do so (probably for good reason - motivations are complex). Regardless, I had a vibrant array of offshoots. Among them:

• Worksheets from the book Designing Your Life

• A list of close friends, and for each: how they inspire me, what they give me, what we have in common, what I could give them

• A list of accomplishments, organized by season

• A list of times I cried, and other lists of meaningful moments in my life

• A list of good stories that I wish to remember

• (and many more)

Living an intentional life

To summarize: each week I opened my journal, read through the week’s reflections, and updated my digital notes. Sometimes I changed my principles, sometimes I made changes to my reflection systems, and sometimes I worked towards setting daily habits that would help me live a principled life.

For at least four years these systems were going strong, and they gave me a strong sense of trust in myself. I knew that every morning I was waking up with the best intentions, and that whenever I fell short, as all people do, I would learn and improve to the greatest extent of my abilities. I was very happy with my systems and imagined them extending far into the future, and yet, I also felt there was much work still to be done. If only I could figure out the right algorithm to integrate everything together - to optimally guide myself into perfect alignment with my deepest values - then the vision would be fully realized!

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Some concluding notes: At this point I’ve covered, from a very high level, the growth period of my living systems. Perhaps you now better understand what it’s about.

There’s tons more I could publish about these systems, much of which is already written (there are benefits of writing about something which was designed to describe itself). Of that, there are many details I’m truly excited to share, such as: what concrete outcomes did these systems create for me? Or, what were the rest of my principles and their full considerations? And, I suppose I might also cover: what happened to these systems? Why is everything in the past tense?

To be honest, to describe the downfall of these systems would be a daunting task. Perhaps I will find a good way to do so, but I expect that to take time. In any case, today’s post was the most important part of the history. Now that I’ve described my prior systems I expect to more easily describe their present evolutions, as indeed a revitalization of sorts is taking place. My next couple of blog posts will probably focus on health, and after that I look forward to returning to this theme.