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General

Probably Going to Drop Substack…Again

I’ve been using Substack again for the last little while and I’m probably going to drop it once again. However, this time, I would have to say the experience was far better than the first time I tried it.

Pros

The Substack algorithm that shows you the Substack Notes (similar to a Twitter Tweet) of other people is actually really good.

When I started using it, most of the notes that were showing had little to no relationship to my work.

Today though, I find the notes are highly aligned with my work.

In fact, I could probably spend the day just restacking notes (like retweeting) and adding my insights to them.

Even more so, this last week or so, when I have restacked notes and added my insights, most people’s responses seemed to be really positive for the most part, especially when I communicate my work from their perspective.

Cons

Substack doesn’t have a Gaming category on it which is absurd. Yet my framework for life primarily perceives it as a role-playing game. Thus to understand it more easily, you need to understand the aspects of a role-playing game. In other words, if I’m using a metaphor and you don’t understand the metaphor, what I’m communicating will probably not be accessible to you. Effectively what I’m getting at is this. My target audience is not on the platform.

To try to get around this, what I’ve tried to do is tag my content in more accessible ways and also include a subtitle that communicates it in a broader way. For example, I have a post entitled “Who is an Adventurer?” and the subtitle is “Embracing the certainty of uncertainty.” Yet the problem is that Substack does not include post subtitles in the post preview within notes, even though notes are the primary way people discover new authors and publications on the platform. So people can’t see the deeper meaning behind the post. (If the section title of the post was added to the post preview, it would help as well.)

Of course, this leads into a whole other discussion about my target audience and the allegory and metaphors I’m using that comprise my framework but I’ll relay that in another post.

PS. I’ve decided to change my Substack publication name to specifically be “Life’s a Role-Playing Game” to make it as clear as possible what its about. Not sure that will do anything though.

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Life's a Role-Playing Game

Embracing the Certainty of Uncertainty

How to become an adventurer of life.

People often say there’s no end to growth because you never arrive at absolute certainty.

But what if the very thing you’re struggling with—your need for certainty—isn’t the obstacle at all, but the pressure that pushes you to grow?

Certainty begins as something essential. It stabilizes you, gives you direction, and helps you make sense of the world.

Eventually, that same certainty becomes too narrow to contain the complexity of the life you’re living.

That tension is the constraint.

And that’s where development happens. The pressure isn’t telling you to abandon certainty—it’s exposing the limits of the kind of certainty you’ve been relying on.

You leverage the constraint by letting the meaning of certainty shift from something you get from the outside—fixed beliefs, fixed identities, fixed maps—to something that comes from the inside: your ability to stay grounded, adaptive, and present even when things change.

That’s how certainty appears within uncertainty: not as knowing what will happen, but as knowing you can respond to whatever arises.

This what it means to be an adventurer of life.

And this is what the adventure of your life is all about.

A true adventurer:

  • Doesn’t rely on stable terrain.
  • Doesn’t rely on a stable self-image.
  • Doesn’t even rely on a stable sense of “capacity.”
  • Does rely on something more fluid: ongoing responsiveness.

They move because movement itself is the grounding.

So the adventurer isn’t someone who has figured out the map; they’ve stopped relying on one entirely. Navigating without fixed bearings, they move with ease and curiosity. The ‘not knowing’ isn’t fear—it’s openness; the ‘not lost’ isn’t certainty—it’s a felt trustin responding to whatever arises.

Lost? No.
I don’t know where I am,
but I’m not lost.

Emile Khadaji, The Man Who Never Missed

This reframes growth entirely: it isn’t about acquiring skills or knowledge to reach a fixed endpoint, but about cultivating the capacity to exist and act within the unknown. Certainty isn’t the goal—it is surrendered. In its place emerges a dynamic, lived awareness that allows the adventurer to navigate life’s hidden levels without being confined by the need for fixed answers.

This is the paradox at the heart of it. In the latter stages of life, the adventurer has “reached the end” not by arriving somewhere, but by fully embracing the fact that there is no final destination. They are no longer chasing certainty or completion; they are oriented in the process itself.

It’s a kind of mastery that isn’t mastery of outcomes—it’s mastery of presence, responsiveness, and engagement. They move through life knowing that every ending is provisional, every answer temporary, yet they are fully anchored in the act of navigating, of participating, of being alive in the unknown.

So one realizes that the journey is never-ending, but the sense of arrival comes from shifting the lens. Arrival isn’t about reaching a fixed point; it’s the experiential recognition that you are already where you need to be in the midst of the journey.

This is how one can be certain in the face of life’s uncertainty.

So your certainty isn’t about fixed outcomes, rules, or destinations—it’s a certainty of orientation. You’ve experienced the process of letting go of the need for certainty, and that lived understanding gives you confidence in the perspective itself.

It’s a meta-certainty: you know how uncertainty functions as the engine of growth, how surrendering the old anchors reveals a deeper, flexible grounding. You can speak with assurance about this perspective because it isn’t an abstract idea—it’s something you’ve embodied through experience.

Do you see the elegance of this paradox?

You become certain about uncertainty, confident without clinging, anchored without relying on fixed points.

That’s the signature of the adventurer mindset: you move through life grounded, not in fixed answers or maps, but in the embodied trust that you can navigate whatever emerges.

It’s paradoxical but precise—certainty isn’t about controlling the world; it’s about knowing you can respond to it.

And this is where life becomes a game—not in the sense of triviality, but in the deepest, most transformative sense. Just like in an MMORPG, the adventurer isn’t afraid to explore the unknown because the unknown is where growth, discovery, and wonder happen. Every challenge, every uncharted path, every encounter is part of the unfolding story.

Play, at this level, isn’t escape. It’s the art of engaging fully with the unknown, of experimenting, testing, learning, and responding—all while remaining fully present. Life itself becomes the adventure, and the adventurer moves not out of obligation or fear, but out of curiosity, joy, and the thrill of discovery.

This is why people are drawn to games like World of Warcraft or other MMORPGs: they offer a safe space to practice navigating uncertainty, to explore new terrains, to take risks and fail, to recover, and to grow—all in a way that feels alive, meaningful, and playful. The same principles apply to life: by embracing uncertainty and letting go of the need for fixed outcomes, we unlock the possibility of living fully, creatively, and adventurously.

In this way, life is the ultimate, epic role-playing game—and you are both player and terrain, explorer and map, navigating the endless quest of your own becoming.

Categories
General

Standing on the Edge of a Cliff of Embodiment

Something feels wrong.

I think what I’m being asked to do by life is to completely let go of my “self” and embody something larger than myself. So it’s about completely letting go of the usual role I play (and currently feel stuck within), that being just trying to explainthings to others which requires a massive amount of scaffolded knowledge to do so.

Instead I’m effectively being asked to jump off a cliff of embodiment and trust that life will guide and carry me, expressing something through me. 

The best way I could explain this is using a quote from the trailer for the Amazon Prime Secret Level tv series…

How many lives would you give…

…just to discover what you’re capable of?

…which mirrors this other quote by a notable author.

You have to die a few times before you can really live.

Charles Bukowski

And it also mirrors something I said a long time ago. 

I’m dying to feel alive.

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General

Shifting Your Point of Vantage

BTW if it’s not already apparent, I don’t have this all figured out.

It’s just that my perspective and relationship to that statement—what it means—is radically different than the conventional perspective of it.

That’s how growth and development transforms you. It changes how you relate to things.

Before you might have see something as “wrong” or “bad” and suddenly a perspective shift causes you to see it as “right” or “good” because you’re perceiving the context of it within a completely new way from a completely new point of vantage.

This is why if I had believed I had everything figured out, life wouldn’t be very exciting and adventurous (although my ego would be happy as a know-it-all). It’s only because I don’t have everything figured out and I don’t know everything, that the unknown and ambiguous nature of life holds so many possibilities and potential for me to explore—a true adventure.

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General

Writing From the Outside Inwards

Something just clicked in a conversation with ChatGPT as to how I can make my work more relatable and understandable without losing the collection of metaphors that form an allegory to describe it all.

Normally I write post titles from a perspective of “within” the allegory. Of course in doing so, readers don’t relate to it because they aren’t “within” it yet but are looking at it from the “outside.”

So the idea is to flip my whole approach around. My post titles and the opening of my posts will focus on where people are at from the “outside” and then I’ll lead them “inside” the allegory by the end of the post.

For example, I was going to write a post which I was going to title “The Great Wilderness” which won’t make sense to anyone. Instead I’ll title it “Why You Can’t Find Solid Ground Anymore (and Why That Might Be a Good Thing)” which hopefully relates more to where people are at.

However in terms of tag use for content organization to organize posts, I will use these metaphors to show the allegory outline as a whole which will allow people to see how the non-metaphor post titles will relate to the metaphor and larger allegory as a whole.

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General

Disrupting Others by Disrupting Yourself

People at the earlier stages of development usually want things to stay the same. So they don’t want people to change, as change feels risky because it can shake the sense of who they are and where they belong.

People in the middle stages start to see new possibilities and often want to help others change and thrive too…but usually in the direction they think is best.

People at the latter stages stop trying to fix or convince others. They paradoxically just focus on growing and being real themselves, knowing that kind of honesty naturally encourages others to grow too.

“Knowing” this is easy. Embodying it is epically challenging.

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General

How to Trust the “Player” Guiding Your “Character”

To visualize this stepping out of one’s “self” to create a sense of psychological distancing, imagine you’re playing a MMORPG game like World of Warcraft as a “player character.”

Your “character” is who you believe you are, your identity / ego as a construct, because you’re so immersed within the game.

You as a “player” represent the boundless you, your soul.

So being able to step out of both your present “self” and future Self is like a liminal moment of being boundless and witnessing yourself outside of time and space. It’s a moment where you become aware that you are not a body with a soul but rather a soul with a body.

So this process is one in which you let go and follow the lead of your larger sense of Self trying to emerge from within the hidden depths and core of yourself.

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General

“Hold the Door!” Hold It Open!

My work seems to be about experiencing ontological dissonance within one’s life which arises from a collection of cognitive dissonance forming a door or portal that can allow one to teleport to a new sense of being.

This portal, however, seems both foreign and dangerous, yet alluring and mysterious at the same time.

The trick with it is to not close the portal prematurely, assuming we “know” what it is and means, but to continually hold space for it, so you can explore the emerging meaning of it daily, like an adventurer making forays and dispatches from a new world which embodies a newer, larger sense of Self.

Artwork by Matt Rockefeller
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General

Me, Myself, and I Am

I once told someone who was struggling through a growth moment, beating themselves up in the process, that there is more potentiality within them than they’re aware of and realize.

I indicated that when they feel compassionate and try to help someone else, think of themselves as that person and apply what they said to them to their very self.

This is not always easy to do though because 1) you need to be able to step outside of your current “self” and 2) perceive yourself as both your future Self helping your present “self” which 3) means being neither of them and both of them at the same time.

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General

From Expertise to Emergence

Why the future of sharing isn’t about what you know but how you make sense and meaning of change as a challenge to your life.

I just had a realization based upon what I’ve been seeing happening online on platforms like Substack.

The old “expert model” of social media was built on stability, where you mastered a topic, established credibility, and then broadcast your expertise outward. It assumed a relatively stable world where knowledge had lasting value.

Then came “learning in public” which was a response to accelerating change. The idea was that transparency and curiosity mattered more than authority. Yet even that model assumed a kind of linearity: you’re on a knowable path of learning something specific, and the social experience is about documenting that path as it unfolds.

But in today’s world, change is not just faster, it’s nonlinear and emergent. What we’re dealing with isn’t just learning new information but learning how to learn in the midst of instability. So the social experience that fits this era might not be “sharing expertise” or “sharing learning,” but something like “sharing emergence” which is about being in visible dialogue with uncertainty itself.

That would mean showing how sense-making and meaning-making happen before learning stabilizes, so when it’s still messy, ambiguous, even contradictory. It’s not about “Here’s what I know” or “Here’s what I’m learning,” but rather “Here’s what’s trying to form through me in real time, even though I don’t yet know what it means.”

That kind of presence fits a world where transformation, not transmission, is the real work.

And this type of presence is what I continually struggle to outwardly express as my mantra of “the adventure of your life,” even though it is a daily inner experience for me.

In closing, I just want to highlight one of the best examples I’ve seen so far that actually embodies this sharing of emergence. It feels a bit messy and chaotic, yet at the same time it’s real and authentic, as though the person is stumbling through a wilderness, trying to make sense of their inner terrain in the present moment.

Years of Destroying What Actually Works by Brad Did