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Questions Help Us to Navigate a Vast Map of Meaning

Conversations with ChatGPT

An extremely deep dive conversation with ChatGPT on how constructing better AI prompts relates to asking better questions for our own growth and development.

AI isn’t a replacement for human intuition and creativity—it’s an amplifier. The key lies in combining your perspective with the system’s pattern recognition to produce something greater than either could alone.

This conversation was inspired by this article below on how are our brains are like vector databases.

Our brains are vector databases — here’s why that’s helpful when using AI | VentureBeat
Parallels between our brains and vector databases go deeper than retrieval. Both excel at compression, organizing and identifying patterns.
venturebeat.com

It’s about understanding how information connects and relates— thinking in vectors, just like our brains naturally do. When you describe a concept to AI, you’re not just sharing words; you’re helping it navigate a vast map of meaning. The better you understand how these connections work, the more effectively you can guide AI systems to the insights you need.

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The Fear of Playing a Larger Role

I’ve spoken in the past about trying to determine what fears are preventing me from sharing my life’s work and a question dawned on me today relating to it (that was sparked by reading my personality profile in more depth the other day). And this question is almost a different perspective of the fears I’ve mentioned before (i.e. fear of not being an expert, fear of not being able to articulate myself, etc).

What if I’m fearful of the larger role I will be playing?

What I mean by this is that in transitioning to a more evolved stage of development and level of consciousness in turn, it’s really about embodying the values with which I wish to live by.

And right now, these values can be encapsulated in two sentences.

I want to be able to fully trust myself, so that I can honestly and authentically share my larger perception and meaning of life, thus enabling me to creatively align and integrate with my deeper sense of Self that is trying to emerge.

I want to embrace my empathy and intuition, so as to collaborate and partner with others in forming alliances that help mentor others in their own growth and development.

This is the bridge I effectively need to build between these two statements of values. And like any bridge, both sides have to have solid foundations or it will be impossible to build.

Thus until I can achieve the first statement and courageous share my life’s work first, the second statement will not be able to be undertaken afterwards.

Thus until I can gain the courage to embrace this first role in heroically sharing my “life as a role-playing game” framework on my own as a sort of “social entrepreneur,” the second role in being a sort of “guild leader” in helping others with how to “level up in life” won’t be possible.

Actually in thinking about this, I immediately reflect back and remember earlier experiences in my life, where I was put within the same situation, but within video game environments.

I remember being fascinated with one multiplayer game back in the mid 1990s so much that I decided to create a website for it to share my tips and tricks on the game. There was of course trepidation, as I didn’t want to look like I didn’t know what I was talking about. But I felt I was highly skilled in the game, so I decided to build it. And interestingly enough, people liked it and it gathered more and more attention over time.

In fact, it gathered so much attention that two leaders from a gaming community wanted me to join them as a third leader of it, as they felt I was quite knowledge about it. But again, while I was somewhat uncertain of my capacity as a leader, I felt like I was as least valued for my knowledgeable, so I jumped at the chance.

This is pretty much what I want to replicate right now. But obviously some fears are preventing me from sharing my work…and, more importantly, sharing my deeper sense of Self.

More and more I think about this, I think it ties into one key value that I haven’t fully achieved yet.

Trust.

I don’t fully trust myself, what I’ve experienced, and what I’ve learnt…even after all two decades of incredible synchronicities leading me here.

It is weird how your ego continually gets in your way.

But I get it. It’s just trying to protect you because it feels like you’re making your “self” vulnerable, thus letting you potentially get harmed.

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The Paradox of the Journey

The experience of detachment and connection at the same time.

In writing my last post, there’s something that popped into my mind at the end of it that I need to write down before I forget it because it’s fundamental to my journey, the paradoxical feeling and experience of it as a whole.

Initially this feeling is one of loneliness.

Why? Because you’re stepping beyond the limited boundaries of the conventional known world of what people believe being a human being means and exploring new ways of being.

So it feels like the threads of your being are disconnecting from the social fabric of society at first.

But this is only because you need to let go of the limiting beliefs that are bounding you and caging you to this conventional space.

Once you step beyond the horizon of your mind and begin exploring a whole new way of being (along with a whole new worldview), you begin to have feelings and experiences of freedom and liberation which feel rapturous.

But while having those feelings, you will continually flip back to feelings of loneliness, as having stepped beyond the conventional boundaries of a societal mindset (which Robert Kegan calls a Socialized Mind).

So you will be riding this rollercoaster of emotions and feelings both of being lonely but also of a profound sense of solitude and connection with something much larger than yourself.

This is you having both a deeper, intrapersonal journey with yourself by exploring the depths of yourself but also have a broader journey with the life as a whole.

That’s because both are entwined. In effect, you can’t transform the way you perceive the world until you can transform the way you perceive your “self.”

The key point I’m trying to make here is this.

You will initially feel like you are detaching and distancing yourself from society (and even those friends and family you love) but what’s really happening is that you are connecting and integrating with something much larger within you and around you that was previously invisible to you.

The best way I can describe this is as this.

It will feel like you are stepping beyond the walls of society as a city and into the borderlands around it to begin to discover yourself. These courageous forays will help you to realize who you truly are rather than what society expects you to be.

And when you have become comfortable with the solitude of the road and the rhythmic, natural way of its being it provides you, you will be ready for the wilderness which lies beyond the borderlands.

It is within this wilderness that you will discover your wild heart, allowing you to shed your bulky armour and walk freely without fear within the nature that lies there. Because that nature is also your nature unbounded.

It is something much larger than most of us can conventionally conceive but with which lies dormant and hidden at the very core of each of us, a boundless potential.

You are not leaving behind something so much as you are embracing something much larger than you can possibly imagine. Something that helps you see yourself, others, the world, and the universe as all part of a larger whole.

This is the paradox of the journey.

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My Personality Explains My Passions & My Problems

How 16 Personalities helped clarify the strengths and weakness of my personality.

If you ask the average person about their personality type, especially Myers-Briggs, you’ll either get back a passionate response about their type, which they feel resonates with who they are, or a just as passionate response saying Myers-Briggs is all garbage, saying their “type” doesn’t make any sense or relate to who they are.

I think the main problem that people have in understanding their personality type though is that it doesn’t describe who you are right now (although it may partially) but who you can grow into and become. Thus a lot of it won’t make sense and have any meaning, until you’ve grow and had experiences that make sense of it as a whole. This is why I believe that personality types should be paired with development psychology, so as to understand this more fully.

For myself, while I try to remain open to everything, I obviously at the same try to use critical thinking to assess the accuracy of things. More recently though, over the past decade or so, I’ve seen dramatic improvements with regards to people building upon these systems and creating hybrid systems that seem much more accurate in assessing your personality type.

For example, 16 Personalities is one such organization doing this, as they combine the Myers-Briggs Type Indicator (MBTI) with the Big Five personality traits, as discussed in their framework. And while they don’t delve into developmental psychology, they clearly indicate that becoming your best self has a lot to do with personal development and growth in understanding yourself which allows you to leverage your strengths and overcome your weaknesses.

Now while I’ve used their site some years back to assess my personality type as a Mediator (INFP-T), which I found fairly accurate, they’ve upgraded their site and add some newer services. Noticing their Premium Personality Report was only $9 US, I decided to give it a try. Upon purchasing it, it provided a PDF titled Mediators Guide to Careers, as well as had me undergo a further assessment test of questions that helped them to further refine their understanding of me.

While I found the test results fairly accurate, especially in terms of my weaknesses (that I was already aware of that I needed to work on), it was the Mediators Guide to Careers PDF that completely blew me away when I started reading it.

Big Picture Thinker

What I mean by this is that how I think and process information to learn something new is radically different from how other people normally do so. For example, someone might learn something by following a curriculum and learning each facet of the new domain of knowledge, piece by piece.

I instead prefer learning in a more open, curious way, almost like you’re exploring a new world. So I’ll be all over the place initially, getting a bigger perspective and outline of the world, by first figuring out its edges. Then after that, I will often deep dive into areas within it. (And hilariously enough, I even do this within MMORPGs, whereby I’ll traverse through zones of a much higher than my own, just so I can get a bigger picture of the world I’m exploring within first.)

So while someone else has completed the first part of their formal course, I’ve gotten an outline of the whole course but haven’t dived into the details yet (although I will probably still have rough grasp of the basics of it).

This is what the 16 Personalities Mediators Guide to Careers PDF also revealed and thus helped me to understand about myself in a much deeper way.

Metaphorical Thinker

Even more so, one other way that I process large amounts of information, so as to make sense of it quickly, is to utilize metaphors to understand it as a whole. Yet of course, when I describe these metaphors to someone else, even if they’re familiar with the metaphor, it can go completely over their head.

For example, this is effectively what I’m doing with my Life as a MMORPG framework. I’m using metaphors within an overarching allegory to package and make sense of highly complex knowledge (i.e. Life as a Role-Playing Game = Developmental Psychology).

This again was highlighted in the 16 Personalities Mediators Guide to Careers PDF but they described this as the ability as creative mnemonics which helps people with my personality type to learn new things, since traditional bottom-up learning methods can bore us to death. Yet I’m obviously using it at a scale and complexity that is way beyond the norm.

Mnemonic: a device such as a pattern of letters, ideas, or associations that assists in remembering something

The Devils in the Details

Now while my ability to see the bigger picture and understand it more easily using metaphors or allegories is an amazing strength, my weakness in relation to this is all but obvious, especially now that I reflect back upon the last couple of decades of my research.

You see, my big picture approach stems from my intuition which allows me to almost magically grasp things much more quickly than other people normally can. But what’s happening when I use my intuition is that I’m making these leaps that let me grasp this big picture much more easily (i.e. exploring the edges of the world as a domain of knowledge).

For myself, this is my ability to 1) see patterns, 2) see the relationships between the patterns, and then 3) see the identity of the system as a whole.

Again think of the patterns as the edges of a new world of knowledge and the relationships helps triangulate these patterns, thus seeing the identity of it as a whole, almost like I’m mapping out this world.

But here’s my weakness. I’m so focused on the bigger picture that the details can often be vague or even unknown.

Now this doesn’t mean I can’t provide an overview of what I intuitively know and for that knowledge overview to be accurate.

But it does mean I have a hard time articulating the details of my life’s work because I often can’t find the rational words to describe it, even though I may have a ton of metaphorical words to use to describe my work as a whole.

Deconstructing My Worldview Brick by Brick

So this is what I need to be doing and this was something I validated some months ago but I’m still struggling with how best to do this.

So again, what I need to do here now is the reverse of what a conventional person would do who learns the foundational elements of a new domain of knowledge first and then builds it up to eventually understand it as a whole.

I need to deconstruct this new domain of knowledge that I’ve created and break it down into bite sized pieces so that others can understand it and learn it in a conventional bottom up way.

But again, upon reflecting back, if I had an implemented something like an evergreen note system which I wasn’t aware of back then, I could have built up this knowledge in bite sized pieces which I could have then just shared with others, as I was learning.

But again, remember that that is not how my mind works. I’m constantly looking for the bigger picture first.

Explains My Difficulties with Note-Taking Systems

Actually what’s really funny, now that I think about it, is that this probably explains why I’m having a hard time grasping how to implement an evergreen notes system. It’s because I’m big picture focused rather than detailed focused on the smaller pieces.

So when I read something in my mind that relates to something else that I read elsewhere in the past, it’s like the relationship between the two pieces of information is more important than the pieces of information themselves because I’m so focused on seeing the bigger picture (which the relationship provides).

Creating a Portal to a New World

And yet, without focusing on the details, it continually feels like I have no solid ground to stand upon which in turn would allow me to build upon it.

Thus it feels like I’m a ghost who is eternally stuck in an ephemeral, liminal world that only I can see as a whole but with which I can’t rationally articulate a pathway to it for other conventional minds.

All said and done though, the more I read this Mediators Guide to Careers, the more I’m beginning to understand my strengths that I can leverage even more so but also my weaknesses that I need to overcome, especially if I want to make my worldview a tangible reality for others.

More importantly though, what it is revealing to me is that I’m not crazy or incompetent, as my struggles in articulating myself and my work often make me feel. I’m just different. And if I can leverage that difference, understanding it as a whole, then I can transform the way I work and translate my work in such a way that others will begin to understand it.

That statement is profound because I’ve describe this metaphorically before. I’ve said that it feels like I’ve discovered this tome of wisdom deep within the depths of myself and a lot of my journey now is in trying to decipher and translate the details of it for others to understand. And that effectively embodies Return stage of Joseph Campbell’s Hero’s Journey.

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What Can Vertical Development Reveal About the U.S. Elections?

Stumbled across this post below on how vertical development relates to the elections in the United States today and provided my commentary on it below, both from the possibility of a late stage leader being drawn to a political position but also the importance of how leaders today need to be higher stages to understand the complexity of the problems we face.

Beyond Red and Blue: The U.S. Election as a Test of Adult Development
Whichever side you might be on, the imminent U.S. election is a choice between starkly different worldviews. What might vertical development teach us about the candidates and this moment?
www.verticaldevelopment.education

What about Nelson Mandela? Yes, a different country but a late stage leader who transformed their country and their people expectations of what a leader should be from a political position.

Yes, America is different, filled with empty talk and phoniness as the norm in terms of politics, but it doesn’t mean it needs to continue that way. It can take a different path if people choose to take one. But if the dominant mindset of the people is based in lower stages focused on having a “strong leader” to “take control” so that “all their problems can just go away”, that’s who people will vote for regardless if that leader has an actual understanding of the problems and plan for them.

This to me is the more troubling issue. That being the relationship between the leaders stage of development and their ability to grasp simple, complicated, complex, and even wicked problems. Lower stages will often think they know everything and have simple answers for complex problems. Yet in trying to tackle complex problems with simple solutions, they may make them infinitely worse.

This ties into what Robert Fritz said in his book The Path of Least Resistance. It’s not enough having a clear vision of where you want to go into the future. You also have to be seeing and understanding the present reality clearly as well. Yet most political leaders today still don’t seem to understand the full breadth and scope of the systemic wicked problems we are encountering today. Having said that though, at least Harris seems like she’d be open and curious to listening to ideas, whereas Trump would just assume he’s the smart person in the room and doesn’t need to listen to anyone.

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Letting Go of Disbelief and Self-Doubt

Reclaiming inner belonging on the journey of growth.

I think part of the problem with growth and development is that so often our beliefs are double-edge swords. They both empower us by allowing us to work within a new space of possibilities but also disempower us by preventing us from seeing newer spaces beyond the one we are already within.

For myself, I think my greatest weakness in this regards is my disbelief in myself which arises from societal expectations and beliefs that I place upon myself and thus beat myself up with. It’s almost like my ego is a bully standing in my own way, crushing my confidence on a daily basis.

This is the main thing I need to let go of. My disbelief in my self, my journey so far, and what is possible for me in the future.

For example, I’ve been on this journey for over twenty years now, since 2001, and no matter how many amazing moments of synchronicity occur in my life, guiding me like quest givers within an MMORPG, I still continually disbelieve all of the amazing things I’ve learnt along the way. That’s because it requires me to let go of the external, societal belongingness that I so desperately seek and instead replace it with a truer sense of sovereign belongingness found within the realm of my inner self.

True belonging is the spiritual practice of believing in and belonging to yourself so deeply that you can share your most authentic self with the world and find sacredness in both being a part of something and standing alone in the wilderness. True belonging doesn’t require you to change who you are; it requires you to be who you are.

Brene Brown
Braving the Wilderness
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Thomas Merton on the Spirituality of Discovering a Larger Self and a Larger World

“A man who fails well is greater than one who succeeds badly.”

Even though I grew up within a religious family, going to church each Sunday as a kid, I wouldn’t really call myself a religious person, so much as I’d describe myself as a spiritual person.

The differentiation for me is important because I think this is the transition and journey my mother went through in her own life. She was deeply religious when I was a kid but by the time I reached my teenage years, she was finding the church life cynical and petty, with people often judging others so that they themselves wouldn’t be judged by others themselves (aka psychological projection).

So she went on a journey beyond religion and stepped into the realm of the spiritual, finding her own way, which gave her life a lot more meaning and gave her a much more personal inner journey and understanding of the basic tenets of religion that I think a lot of religious people today are completely missing. It’s not about what’s happening out there and what other people are doing wrong. But about what’s happening within you and how you can let go of these things that are not letting you be the person you want to be (and who you already are deep down inside).

This touches upon my discovery (via Margaret Wheatley) in the past of Thomas Merton, an American monk and writer, and some of the quotes from his writings that I’ve only recently read in-depth.

For example, this quote below touches upon a mantra of mine which is “work on living what you’ve learnt through play.”

A purely mental life may be destructive if it leads us to substitute thought for life and ideas for actions. The activity proper to man is purely mental because man is not just a disembodied mind. Our destiny is to live out what we think, because unless we live what we know, we do not even know it. It is only by making our knowledge part of ourselves, through action, that we enter into the reality that is signified by our concepts.

Thomas Merton
Thoughts in Solitude

What I find fascinating about his work and writings though is that in some of his most famous quotes, you can see someone who is on a spiritual journey of self-discovery that resonates closely with what Joseph Campbell describes as The Hero Path, where at “the center of our existence” we aren’t alone but “shall find God” and “be with all the world.”

In Louisville, at the corner of Fourth and Walnut, in the center of the shopping district, I was suddenly overwhelmed with the realization that I loved all these people, that they were mine and I theirs, that we could not be alien to one another even though we were total strangers. It was like waking from a dream of separateness, of spurious self-isolation in a special world…

This sense of liberation from an illusory difference was such a relief and such a joy to me that I almost laughed out loud. . . . I have the immense joy of being man, a member of a race in which God Himself became incarnate. As if the sorrows and stupidities of the human condition could overwhelm me, now that I realize what we all are. And if only everybody could realize this! But it cannot be explained. There is no way of telling people that they are all walking around shining like the sun.

Then it was as if I suddenly saw the secret beauty of their hearts, the depths of their hearts where neither sin nor desire nor self-knowledge can reach, the core of their reality, the person that each one is in God’s eyes. If only they could all see themselves as they really are. If only we could see each other that way all the time. There would be no more war, no more hatred, no more cruelty, no more greed. . . . But this cannot be seen, only believed and ‘understood’ by a peculiar gift.

Thomas Merton
Conjectures of a Guilty Bystander

I think this is in the deeper sense the connectedness that underlies all religions, yet is somewhat sadly blocked by most religions, as each one often sees their view of the world as superior and right compared to the wrongness of others. So often most religions stand in their own way, just as our own ego stands in our own way as well.

If you can get past this limiting view of the world though, as Thomas Merton did, you can discover a whole new way of being and a whole new way of perceiving the world. This is just another way of describing what vertical development is to me without calling it “vertical development.”

It is liking climbing a mountain into your “self” but with each progressive vista completely shattering and upending the way you view the world and your “self” as a whole.

For me to be a saint means to be myself. Therefore the problem of sanctity and salvation is in fact the problem of finding out who I am and of discovering my true self.”

Thomas Merton
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Reducing Distractions Via RSS Feeds & Unread App

I use the Flipboard app almost on a daily basis, so much so that I often end up doom flipping through it. I think this is a weakness of my explorer mindset in that I’m constantly exploring for new things that relate to my life’s work. Yet this can obviously pull me down rabbit holes where I completely lose track of time, wasting away the day.

Even though I love the way the Flipboard app works in terms of flipping between articles, my number one issue with is that it no longer supports native RSS feeds (even though it is at least embracing the Fediverse).

Another huge issue with Flipboard is that it’s main “For You” feed continually dumps in news that you may not be interested in. Yes you can use the filtering options to say you want “more” or “less” of certain topics (although it very confusing how this works) and you can also completely “mute” a news site if you like as well.

However muting sites actually occurs locally on your device rather than the cloud, so on slower, older machines, it can dramatically slow down the Flipboard experience, as you could end up waiting multiple seconds everyone once in while between flips, as your device filters out certain new sites you no longer want to see from the newer articles being loaded.

Realizing that using Flipboard is overwhelming me by continually distracting me, I’ve decided to go back to an RSS feed app on my iPad called Unread that I used briefly before.

While the basic functions of the app are free (with advanced features included for a monthly or yearly subscription), I find the basic functionality more than sufficient for my needs. In fact, if I was to pay for it, I’d prefer a single payment lifetime option, as well as more options for changing the formatting of what you’re reading (i.e. line height, width, etc).

Nevertheless, it still meets my simple needs in a simple way. And I’m enjoying reading again from people I’ve subscribed to in the past, as well as some newer people as well.

The best thing of all is that when I’m finished reading and go back to my overall list of feeds, I eventually reach a point where there is nothing left to read which gives this strange feeling of being able to just breathe again. Almost like you can finally exhale again after inhaling too much.

But I guess that relates to the rhythm of being creative. Breathe in for inspiration. Breathe out for creation (which hopefully connects with and inspires someone else in turn).

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Rediscovering That Authentic Old School Feeling of Blogging

How the Bear blogging platform is reinvigorating the blogging ecosystem.

While checking back and seeing what Derek Sivers is up to, I noticed him referencing Bear. Assuming he was talking about the Bear app, I quickly discovered he was referring to the Bear blogging platform instead which is a creation of Herman Martinus.

Shun the bloat of the current web, embrace the bear necessities.

Bear Blog

While highly impressed with the platform as an extremely minimalistic way to blog, what I really loved was Bear’s Discover page which lists the trending and most recent blogs on the platform, as well as a way to search for blogs by keywords.

While browsing through some of these blogs, it totally gave me that old school feeling of blogging from years back which is really nice to see in our overloaded and overwhelming world today.

At the same time, it amazed me how you could create something so simple and yet still foster authentic connections between people without resorting to something much more massive like what the Substack platform has done.

Don’t get me wrong. I think what Substack is achieving is amazing in itself as well, especially with regards to giving people a writing platform to make a viable economic living on. Yet at the same time, I find the Substack platform can be overwhelming and distracting at times, so the simplicity and distraction free nature of the Bear blogging platform is great to see.

I guess that’s the paradox that most of us are looking for in wanting both individuality and collectiveness at the same time. We want to create a safe space where we can daringly be our authentic selves (beyond what other people might initially think we are), yet at the same time find a community of others who resonate with the language we speak and metaphors we’re using in expressing ourselves.

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Vertical Development

Using Solid Patterns to Rise Above the Overwhelming, Detailed Flows

I just had an interesting conversation with Claude.ai that started by asking how to shift your mindset from blogging to taking notes using the evergreen note method. It overwhelmed me with its response but a key takeaway was to shift from a diary approach of “What I did today” to “What am I exploring”

What this made me realize was that I’m often stuck in the details of what I’m exploring so much so that I often forget what I’m exploring. This effectively feels like being stuck in a maze, going in circles, because your viewing things very close to ground rather than having a strategic birds-eye perspective of things.

Realizing what Claude.ai was talking about, I asked it if it meant that I should focus on patterns rather than talking about the details of the patterns so much and it said that’s exactly what it meant.

Why this is important is because this is something I’ve known for a while but have yet been able to construct and organize upon a website, rather than just within my mind.

Basically my internal mind approach is as follows.

See the patterns.
See the relationships between the patterns.
See the identity and big picture of the system emerging overall.

Again how to show this on a website is what I struggle with but I think an evergreen notes method of interlinking smaller, atomic notes would help achieve it. Yet I struggle with how to start this.

Anyways when I realized what it was telling me to shift my mindset, I asked it if it could be applied to shifting one’s mindset for vertical development and it said it could.

It said to focus on patterns that relate to transforming yourself and your mindset, like 1) perspective-holding capacity (i.e. open to multiple perspectives), 2) identity transition (ie letting go of expert mindset), and 3) paradox navigation (i.e. letting go of seeking closure).

This approach, focusing on patterns, creates something that one can stand upon within the detailed flow that creates the pattern itself.

In closing, Claude.ai indicated the following which really hit home in terms of how I’ve been feeling lately. Both in terms of feeling stuck but also being able to stop and sort of rise above the flow in a liminal moment, witnessing it pass me by without it overwhelming me.

Instead of seeing your “stuck-ness” as failure, you’re tracking how your capacity to hold complexity is actually developing, even when it doesn’t feel like it.