It’s been nearly a year since I put out a Compass Point, my longer newsletter segment that is more of a conceptual deep dive rather than an anecdote or check-in. When I first started Cultivar, I thought I’d be able to put one Compass Point out a week … I learned quickly that was too exhausting.

One of the greatest and hardest lessons I’m learning in this pursuit of authentic alignment in my life is recognizing where and what drains my energy, whether emotional or mental.

The most surprising thing for me is that these days, expansive thinking endeavors, such as writing a long form essay, take up way more mental energy then they used to when compared to positive interactions and conversations with people, particularly those who are just as passionate about what they are building as I am.

The intersection of community and creativity is where we find good leadership, and that’s where this compass point is taking us.

The other week I had a very energizing call with , founder of seeq.ing, I’d highly recommend checking out his vision here.

Over the course of an hour we discussed how he wants to revolutionize the way travel creators monetize sharing their journey and experiences, shared some of our philosophies on AI, what it means to be a true leader, and what the landscape of meaning and leadership will look like beyond our horizon; not in just 10 years, but 20, 30, and 40 years from now.

We both agreed that the future of leadership lies in human connection and authenticity, and though we had a few variations in what we felt it might mean to be perceived as authentic versus resistant to embracing AI and change, there was one statement I made that Jon loved so much he insisted I put out to the world:

Despite completely believing in my assertion, and it being one I think I’ve made before in conversation, no one has ever asked me to unpack or explain it; so a huge thank you to Jon for for inspiring my rabbit hole of the past week.

To the leaders current and future that are reading this, I hope you enjoy the following exploration of how our capacity to lead may be threatened by the ever-narrowing ways in which our brains have become rewired for enclosure, hyper-specialization, and efficiency.

It’s a bit long and messy, but I hope you’ll trust me and engage in the comments, because the future of leadership lies in authenticity and regenerative thinking; and systems thinking is modern animism for the corporate world (I’ll explore that last bit in another segment).

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History of “The Commons”

“Savoir, Penser, Rêver, tout est là.”

Victor Hugo, Preface: Les Rayons et les Ombres

A Connective and Regenerative Past

// commons: open land or resources (cultural or natural) belonging and available to the whole of a community to ends of both individual and collective benefit.

If you aren’t familiar with the term “commons”, it generally means the land or resources belonging to or affecting the whole community. It’s most commonly (pun intended) been used in my experience and education to refer to the land resources that were available for public use during the Middle Ages up until the advent of both private and personal property.

More than just land for enjoyment, such as our national parks here in the U.S., the commons included water, fisheries, hunting lands, and farmable land for community use and everyday life that, while governed, were not as restricted in who could use them when compared to private land ownership.

The term originates in a worldview where community was relational, supportive, and self-sustaining; something that, across the board, I see many people longing for.

A semblance of connection that is felt rather than labeled, whether at work or in our personal lives. We are more than our follower counts and org charts.

There are some who romanticize medieval village life because of how far removed our society is from that small, tight-knit sense of being, but on this front, I find a few problems with romanticizing it.

• First, what we are chasing is a feeling that we assume we will find if we regain the commons through physical means and intentional living. Assumptions are often the enemy of joy and meaning. Reclaiming the physical commons and living intentionally will only nourish us if we can connect deeply with one another and our surroundings.

• Second, the worldview that could have supported that type of intentional living is (nearly) impossible to regain; more than 1,000 years have passed since that time, and our entire conception of being has undergone significant changes (even more so in the past 150 years), something Daniel Lim has come to understand and written about extensively (I would highly recommend reading this article of his: "Building Regenerative Cultures").

• A third point of note, is that the concept of the medieval commons are a Eurocentrically focused snapshot of the last breath of the regenerative connective worldview found in early animistic belief structures throughout Europe; other (and often indigenous) cultures from around the world are being studied now by the West in an effort to understand regenerative structures and processes with applications toward urban planning, agriculture, climate preservation, leadership and more.

But that feeling of relating, of community, of belonging, and having a space that you can draw from to support living your life is reified when we try to emulate what was found in the past.

// reification: treating an abstract thing as concrete; particularly in the context of needing to simplify a concept to express an idea.

Feeling connected to a community and of having worth outside of what we provide to our society is absolutely something that can be found and adapted in the modern world; it just takes creative, new ways of thinking that are deeper than what we are used to. There is no way to go back to a medieval-era commons way of living and worldview (absent apocalypse).

In the modern era, engaging in authentic connection and exercising agency in the commons involves challenging the assumptions of our self-awareness and as well as how we relate to those around us. The ones who do this successfully are leaders by virtue of this alone.

As time has gone on, the term “commons” can (and is) applied to a much broader set of understandings than open land for food and natural resources. Healthcare, education, internet access, communication access, and the digital cloud are all examples of intangible yet highly important commons that many people need access to in order to thrive in modern society.

Yet for millions of people, these “commons” are still placed externally to our understanding of self, and we still pay for access rather than having an open door policy for thriving. Why is this?

Because our understanding of the commons and its applicability to creative, authentic leadership is incomplete without also understanding the role of enclosure.

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Realities of Enclosure

// enclosure: an area sealed off or separated with a barrier, artificial or natural.

The terms Commons and Enclosure both originate in the English common law understanding of land ownership, with enclosure being a process of appropriating the commons from public use into private or institutional ownership and use, often in the name of efficiency or increased profits.

When the term “public use” is brought up, you might think of access to a park, a river, a community garden, the office breakroom and kitchen, or a public restroom, but there is one often overlooked aspect: agency.

The value of the commons didn’t lie only in its availability for all, but rather in the ability to exercise one’s agency and self-determination in the use of public land.

You didn’t need to ask permission, but you did need to respect the rights of everyone’s access to the commons, because everyone and everything had intrinsic value, and if you took more than you needed, you trampled on the rights of others and upset the balance of regeneration.

Agency must be balanced with discernment, and “a living system is regenerative if it keeps creating more life (itself) or creates the conditions conducive to more life.”1

The enclosure of the English countryside led to dissatisfaction and riots throughout the 18th and 19th centuries. Upon examination of the subtext, it becomes clear that the riots were a response to the erosion of the agency and rights of the common folk to live and thrive in places where they felt a deep, ancestral, communal sense of relation.

As the inability to make ends meet spread, artisans and creative people who lived in more urban environments also began to protest, because the enclosure eventually affected everyone and made them reliant on enclosed systems rather than regenerative open communities.

We often talk about finding our tribe, our people; what we are looking for is a sense of tangibility in both being seen and being impactful; belonging and being. Accepted.

The commons (whether community or resource) serve as a physical representation of our innate right to thrive.

Historically, leadership roles, often thought to be the most “high impact”, are seen as lonely and isolating, but an increasingly larger percentage of people feel isolated despite the connective, communal narrative of social media and increased online presence.2 Whether at work or in person, deep and authentic connection seems harder to find.

It’s worth asking then, if modern levels of loneliness and isolation are an imposed fallacy by the hierarchical nature of the structures most commonly used to enclose different aspects of an organization for control and efficiency.

Perhaps without realizing it, proponents of systems thinking are in fact attempting to reclaim a regenerative, animistic understanding of how people and their environments relate to one another.

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The Modern, Intangible Commons

Throughout the 1900s in the U.S., apart from protected places like Yosemite, Yellowstone, and the Great Smoky Mountains, the commons largely shifted from physical land-based resources to those of a digital format.

Work, news, and shopping for necessary (and unnecessary) items are now things we do through an app, rather than touching grass, looking up at the sky, and interacting with our community. To feed and clothe ourselves, we no longer need a direct relationship with the physical commons, nor the people who make the goods or grow the food.

In the 21st century, the disassociation is going one step further.

The cloud, an “enabled network access to a scalable and elastic pool of shareable physical or virtual resources with self-service provisioning and administration on demand,” which provides access to so many necessities with AI, website hosting, and the like, is the current commons at risk of being enclosed.

If you don’t believe me, read this segment of an article from , who has explored the topic much more in depth than myself:

Once they know what they need, platforms become incredibly generous. They create "open" ecosystems, practically begging developers to build on top of them. Free API access. Viral growth mechanics. Revenue sharing that seems too good to be true.

Why? Because they need you. Your apps, your content, your data, your innovations— they all feed the moat. Every developer or creator who builds on the platform makes it stronger and harder to displace.3

It may not happen to the extent projected, but think of who has access to the cloud versus who has control over it. Amazon, Microsoft, and Google operate the largest “hyperscaled” cloud computing providers.4

If they decide, for whatever reason, to limit (via Balfour’s three step cycle) access to individuals, organizations, or populations in the name of efficiency (maybe you only get to have a certain amount of data storage for the pictures in your cloud drive, or you don’t outright own downloaded movies you’ve paid for), you lose access to the digital commons.

If you are a creator, an entrepreneur, an influencer, a job seeker of any kind, someone who relies on apps to pay your bills, connect with friends, order food or groceries, then you are the commoner to the modern commons. You rely on these digital, intangible commons, these currently available spaces and resources to ply your trade and explore your sense of self.

That sense of self is a form of the commons that exists in our human-ness, our authenticity. Our ability to think creatively, innovate, and build, adapt, and overcome - this is something we’ve always had access to, so long as it is cultivated through new experiences, starting in childhood through education, libraries, community playgrounds, and playing with others (both inside and outside).

I don’t think I need to cite an article to discuss the state of the American education system, but by way of personal anecdote, I have taught a few college classes and have friends and family in the pre-K through university-level teaching professions. It has been our experience over the past 20 years, particularly the past 5, that our capacity to learn, and thereby think creatively, has become severely hampered.

We must ask why (not that the question hasn’t already been posed), at a time when we have the wealth of knowledge at our fingertips, analysis and observation tools beyond the comprehension of Ibn Battuta and Newton, and ability to connect with any perspective on the planet, our youth (and adults) find themselves increasingly limited in its ability to retain and synthesize information, and why we all seem to be facing an authenticity crisis.

My answer to this question is the same to the one I posed earlier on isolation and loneliness: mental enclosure.

Mental Enclosure

I’m a Millennial, and if I’m being completely honest, I’ve had to fight to keep the long attention span I had in childhood over the past 10 years or so, with the intersection of ADHD, algorithmized social media and short-form content, and a traumatic brain injury making it hard to follow through on finishing out creative endeavors.

My brain is becoming increasingly enclosed by dopamine hedges masquerading as neural pathways.

I won’t go so far as to say enclosure of the English countryside is the seed that eventually sprouted into the hedge rows of full-blown isolation and mental fog many of us navigate in this digital age, but it certainly looks to be the point at which people began to feel disconnected from the land and their community.

It does seem like a likely candidate for what nudged us to pursue something intangible rather than relational. We’ve confused presence with purpose, and in the exchange are unable to navigate by our own senses.

• I remember a time, pre-internet, when I would come up with random stories in my head, write poetry, and brainstorm ways to fix problems with ease.

• I would also pay more attention to my surroundings on trips and playing outdoors rather than taking pictures all the time.

• I could sit with curiosity and explore options without needing an instant answer. The more I exercised this, the more creative I became.

• I think that in a large part, much of my upbringing was rooted in being present in the moment, fully engaged in whatever activity I was doing, whether that was reading, building a fort or Legos, or watching TV.

There wasn’t a sense of needing to know immediately, be connected, and on top of everything, everywhere all at once, and even if there was that drive, I had to explore commons in order to find the answer in libraries, conversation, and experience.

These building blocks set me up to fully explore what lit up my brain on my own terms, how I connected and related to the people and things around me, rather than seeking quick dopamine fixes and instant answers.

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Now, the neural hedges are so tall that that even if I wanted to step off the quick and easy path I’d have to expend effort to cut a hole in the hedge, or just keep going. They are something I’ve been trying to cut down with keystrokes and the internal fire of passion projects.

My creativity, my ability to “think outside the box,” was one of my strengths that became evident as I took on leadership roles throughout my 20s. It allowed me to strategize, empathize, and come up with ideas for crises and conflicts without needing to ask someone else, “What should I do?”

I still asked for feedback, opposing views, and perspectives from those on my team, my peers, and higher-ups, but it was to address the blind spots I knew I had, and I could do so because of the relationships of trust I had cultivated.

I only knew I had blind spots, because I had access to and engaged with the commons of creativity; the world of perspective and inspiration that only comes through deep, passionate work, exposure to other points of view, but almost most important of all, the ability to quiet my thoughts and sit still, focusing on the task at hand.

That stillness, that ability to let an answer form rather than appear, was an incredibly important filter that allowed me to see relationships between the commons and my lived experience,

Now, it seems, that my foundations for creative growth have become enclosed.

• Stories and poetry don’t always come as quickly or naturally as they used to.

• I Google answers to problems rather than looking at the situation first and taking a guess.

• I’m always taking pictures on my phone to send to family or friends rather than being present in the moment.

The different components of my human experience are becoming increasingly disconnected, to use a the corporate term for enclosure, “siloed”, something that an excellent writer I subscribe to, wrote on recently.5

Particularly as I’ve become a father and a full-time remote worker, if I don’t make intentional space for creative thinking, it manifests in a disjointed manner, and this has drained my energy, bandwidth, and consistency for working and leading.

Through technology (and I primarily blame social media), my ways of thinking and relating, whether concepts or community, have become repetitive, manipulated, and reified; this phenomenon is becoming a stronger and more pervasive force for the generations that have grown up in enclosured digital spaces and mindsets.

Whether optimizing for algorithms, trying to find our voice, or leading others, as a society, we are becoming self-limiting in the name of achieving success and presenting ourselves to the world. My dear friend and mentor, Grace, sent this clip to me other day, and I think it is relevant to the exploration of creativity as the commons:

There is a fine line between understanding something and limiting it. Accepting the answers that AI spits out without critical analysis or engaging with it prior to exercising our own agency runs the risk of enclosing ourselves from the very thing that will separate our intelligence from non-organic intelligence.

Commons and the Future of Leadership

Regenerative Growth is a Mindset, not a Procedure

The moment something becomes standardized, it is limited, enclosed, and the capacity for regeneration is reserved only for those who control the enclosure. Thus, we cannot underestimate the dark power of optimizing for algorithms, templated leadership development courses, or easy labels that tell others what we are rather than expressing who we are.

Even more so, we must be vigilant against letting artificial intelligence do our thinking and our creative work for us. Once we’ve served our purpose with making the digital commons valuable enough to enclose, will our brains be strong enough to build a bulwark to defend the last remaining commons, creativity?

A relevant point from Jon’s latest post exemplifies this:

Platforms operate on extraction economics. They need to capture value to survive. But what happens when the value generators, the creators… realize they don't need those old, harvesting platforms to reach their audience?

When the infrastructure for independence exists? When users prefer human curation over algorithmic recommendation?

These platforms' moat was distribution. That moat is dry. Their castle walls are crumbling. And they're responding by building higher walls instead of recognizing the siege is over.6

What Jon has connected the dots on in both his article and with his vision for seeq, is the connection we are craving in all aspects of life: authentic and sustainable connection. By and large in acceptance of our neural dopamine hedge rows, we don’t value our own authentic selves; we value attention and fitting into the molds society provides.

Capture is the active process of enclosure, a procedure of extraction that removes value from the commons rather than sustainably regenerates it; this happened in the name of efficiency with land enclosure, and it is happening now with the digital commons.

The best example I can think of off the top of my head that illustrates the enclosure of creativity into a commodity is the transformation of Etsy into a hustle culture platform that prioritizes sales over artisans, despite its initial launch as a democratizing effort that traded creative love, labor, and time for profit, rather than relying on storefronts and corporations.

Tying back to Daniel Lim’s thoughts on regenerative culture:

What could be more sacred than what makes us human in an era where computers have the capacity to perform scientific and managerial procedures absent our input?

If our very ways of relating, understanding, and creating are extracted for value rather than respected as being an expression and exploration of self, what are we to do against these enclosures?

Once the artisans are gone, will the creative thinkers, writers, and philosophers be next?

“Savoir, Penser, Rêver, tout est là.”

One of my favorite quotes of all time comes from Victor Hugo: “to know, to think, to dream: that is everything.”

To know - we must gather knowledge, whether books or lived experience. Knowledge serves as the foundation of both our authentic selves and our agency in navigating and impacting the world.

To think - knowledge and intellect are not the same. We must be able to critically analyze information in order to form our own opinions and make sense of the world. Thinking involves challenging ourselves as much as others, and it takes active work and engagement to do so.

To dream - the more we know, and the better we can think, the bigger we can dream. Bigger, not in the sense of exponential growth, but bigger in terms of what is possible.

That is everything - those three things and their relationship form the basis of human experience and understanding. So access to knowledge, neuroplastic cultivation of our cognition, and the autonomy to dream as we see fit, while amorphous, are another intangible commons.

As I said, I remember before the advent of social media and short-form content that my brain gathered knowledge and analyzed it differently. I still have the capacity for creativity, and in fact, it’s something I try to cultivate through new experiences, connections, and perspectives, but the soil that fuels my creativity is lacking the nutrients it once was.

I know AI is here, and it is going to become more efficient, revolutionizing many aspects of our world. I know it helps many people and friends in my network ( , , and to name a few) with their work flows, bringing ideas to life and freeing up their time to invest more in things that nourish them.7 But these are individuals who exercise discernment and agency.

My fear is that, AI will be implemented with speed and scale in such a way that proves to be more of a long-term hindrance to the uplifting and empowerment of humanity rather than be a democratizing equalizer for the majority of people.

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From an article I read recently, AI has the most usefulness to those who already have a decent level of expertise and critical thinking in a particular field that they are using AI to augment their work in, because they are able to tell when it is wrong.

They are able to question, by way of knowing and thinking, and continuing to dream rather than conform.

So when Jon asserts that he has “increased capabilities 100x in three months via AI”, I believe him, not because of the power of AI, but because of the relationship Jon as an authentic person who loves travel, cameras, Star Wars, and Dragon Ball Z has with AI - his creative, intuitive self with knowledge of disparate arenas of the human experience, knowing where his boundaries lie, what patterns are applicable to surface level irrelevant fields, and how to wield technology to push him further and harness his creativity and understanding.

If Jon didn’t have preexisting depth of knowledge and experience, have rabbit holes of curiosity and passion that intersect in a uniquely Levesquean way, I would expect his capabilities to only increase marginally through the use of AI, and plateau out along with the majority of of people who are adopting and implementing it without a critical or creative lens. I would expect his ideas, his writing, and his goals to be performative copies of everyone around him a la trending TikTok dances and em dashes.

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That is my concern for the future; what I think is happening with the majority of our youth, and our current senior-level leadership. Both extremes think the immediate and unquestioning adoption of artificial intelligence its the answer to all the problems they face, whether its bottom line or getting by.

There is no authenticity in AI; all it generates is the amalgamation of knowledge gathered, no new, creative thoughts.

To paraphrase the words of David Baldacci, yes, creatives do read, watch, and synthesize the work of other authors, artists, filmmakers, and so on, but they do not directly copy (unless they want to risk a lawsuit). They get inspired by, they grow and experience life through this process of understanding the diversity of others’ authentic selves and expression.

My fear is that the managerial approach to leadership that so often maintains hierarchies and toxic behaviors extracting value, purpose, and agency will determine the future of how AI is navigated and implemented - I think it is already shaping up to be that way.

If our future generations become increasingly siloed from the creative commons by way of more efficient algorithms, tailored ads, lack of access to basic infrastructure, and intangible commons of education, healthcare, critical thinking, and more, how will they lead? How can we ask them to?

How will they be able to link disparate concepts and see patterns when everything is built to concentrate their thinking according to the busy neural pathways of ease, efficiency, and instant gratification? Will they need to think?

Conclusion

I don’t have all the answers, I’m just seeing connections and trying to make sense of them. However, I do know that we can’t raise leaders who are disconnected and enclosed off from the very thing they are leading.

The world is the same size it has always been, yet there is more in it than ever before in our entire history. But it feels smaller, as though there is less, because of our increasing disconnect in how we relate to others and the world.

This disconnect comes from our minds and perspectives becoming enclosed and siloed in ways of thinking that keep us controlled and unable to envision new paths forward.

Technology has the capacity to democratize agency, by and large, I’m not advocating for everyone to become a Luddite; I’ve seen many creative leaders utilize AI with the best intent and to great impact, and I believe Jon is one of them, along with people I’ve worked with like .

However, particularly for leaders who are thinking of using AI to get ahead by fitting a mold that makes them feel more acceptable or presentable or implementing AI en-masse to cut costs or compete: tread carefully, and don’t forget that you lead people through authentic connection, not algorithms.

Millennials and younger need community and purpose just as much as they need a paycheck, so show up authentically, and ask yourself the following:

If you have read this far, thank you for working through this entirely-untouched-by-AI essay.

I intentionally wrote a long form essay to exercise my abilities of “Savoir, penser, rêver,” it took longer than expected and was a challenge to not give up and write something shorter, or narrow down on one aspect of the concepts discussed. But while I still need to be more discerning in my writing, we must dream. That is where hope comes from.

If anything in this Compass Point has resonated, I ask that as you learn and incorporate AI into your processes and workflows, you also lean into your creativity just as much, and that you respect the connections between you and your people.

Explore every facet of connection, feeling, and emotion that you can.

And so we must give equal importance to literature, arts, language, travel, and community - any aspect of life that nourishes our very being and connects us to one another.

Find purpose beyond endless optimization and growth; curate things that inspire you, and share them. Otherwise, what are you optimizing for?

I believe everyone deserves good leadership and that many of the challenges we face in the world today stem from inauthentic, toxic leaders; from extractive structures and behaviors that prize value and efficiency over unlocking the potential in the human race.

To reword Daniel Lim’s excellent quote on regenerative systems:

This is why I believe so strongly in authentic leadership’s role in the coming era.

Authenticity is regenerative. The soil of authenticity is creativity. Creativity is nourished by our capacity to learn, a fundamental aspect of our humanness that allows us to see the relations between disparate concepts.

Because maybe in actuality, creativity isn’t the new, but last remaining commons.

And unless we cultivate it, artificial general intelligence may enclose it entirely.

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Thank you so much for reading this exploration of ideas. If something resonated, or if you disagree entirely, I’d love have a conversation with you and hear your thoughts and your story, either in the comments or privately.

You are more than welcome to reach me via chris@cultivarleadership.com, or any of the following:

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Footnotes:

Many of the failures and victories found in any aspect of life revolve around the perception of permanency, and the absolute belief in the process of growth you choose. At the organizational level, it’s often the leader’s conceptualization of their available choices, organizational capabilities, or interpretation of their arena that determines how victory is understood. Whether fighting a counterinsurgency or competing in business, in retelling Arthurian legends or forging success as an independent rapper, myths constantly shape the choices leaders take.

Counterinsurgency is a Racket of Assumptions

The exploration of myth has taken me back to my days researching insurgencies and irregular warfare strategy. There was one book that changed the course of my mindset, Illusions of Victory: The Anbar Awakening and the Rise of the Islamic State by Carter Malkasian.1 Having been raised in the U.S. Army infantry on Petraus’s Counter Insurgency (COIN) Doctrine, when I entered university I aspired to work for the intelligence or defense industries as an expert on organizational structures and strategies of insurgent and terrorist organizations. I had been led to believe that COIN worked, yet in the years between leaving active service and going to college, ISIS had swept through and violently retaken most of Iraq.

The burning question in my mind, was why?

How could this have happened, when we had so much success that one of my deployments was canceled due to the withdrawal from Iraq - we had won, right? The Iraqi government and military had secured and stabilized things, thanks to our intervention. Ah, yes, that was it.

Thanks to our intervention. Not their own agency.

As I quickly dove into my first literature review of undergrad, I realized everything I had learned about insurgencies was from a tactical and regional level strategic point of view, and a Western one at that. They don’t talk much at the lower enlisted level about the geopolitics of strategy. It’s a shame really, I know a lot of smart people that could have told the strategists the lessons that would be learned after we left. And in fact, there were people at all levels of leadership that did see the writing on the wall, but ignored it, which Malkasian discusses regarding the fall of Iraq to ISIS:

“We missed these signposts. Success over-wrote them. The Tribal movement’s success was so militarily impressive that we mistook it as irreversible, rather than a momentary break in tribal infighting.” (Malkasian, 2017, p. 22)

The illusion of victory. The celebration before the finish line. The assumptions of supremacy because we had confirmation bias that western democracy and warfare had prevailed. Or maybe we were just tired and leapt at the chance to be right because that meant we could come home. What the rise of ISIS showed us, is that the resistance to Al-Qaeda in Iraq had not been because of an Iraqi - envisioned, self reliant movement. Without U.S. backed funding keeping the tribal leaders in power, everything crumbled.

The book is a quite excellent expose on how the interpretation of victory by either side determines what “victory” looks like in long run. It details how long term change, (within the contexts of the book discussed as intervention), cannot take place with a just a few years effort, and furthermore, requires buy-in from relevant stakeholders - in this case the leaders and people of Iraq. One of the key takeaways, which Malkasian regards as a major lesson regarding these types of conflicts, is that:

“Social and cultural factors underlay the outcome. The larger meaning … is that the course of an insurgency, an internal conflict, or a civil war may be determined by unmalleable internal dynamics more than the actions of an outside power…” (Malkasian, 2017, p. 20)

The interesting aspect of Malkasian’s work is that the lessons learned are particular transferable to other businesses (If you don’t believe that war is a business, take it up with Marine Corps Major General Smedley Butler, author of the book War is a Racket).

How many companies or organizations generate sweeping success, whether in sales, R&D, you name it, only to not have it work in subsequent years or different sectors of the economy. What myths were being told by the leadership, the established authorities? The company was too big to fail? The customer didn’t want the feature the competitor had, or that it wouldn’t be much of a threat (A la BlackBerry executives circa 2007)?2

And yet there are massive companies with such hierarchy and structure that they couldn’t possibly be equated to insurgencies, such as Haier and Cemex, that have success for the very same reasons as insurgencies do. They challenge their industry’s myths on how to succeed.

While what generates myth, what is behind the remembered terrorist attack, or the unveiling of the newest technological marvel, is the people, process management, and innovation that keeps these organizations marching forward. No organization can thrive without the buy-in and effort of the strategic implementers, and this is why leaders must foster a positive culture that empowers every echelon of worker. When everyone is empowered, the standard operating procedure for the company becomes a flow of innovation. Process management becomes second nature, not a constricting chains of conformity leading to micromanagement.

This concept is clarified in another book that challenged my assumptions on insurgencies, The Terrorist’s Dilemma, by Jacob N. Shapiro, who argues that successful insurgent and terrorists groups don't “win” because of the big events, but by managing the mundane. Behind all the purposely visible and heinous acts, is logic and organization. Despite the obvious difference in the arena of competition, insurgents are for all intents and purposes the violent equivalent of Clayton Christensen’s “disruptive innovators.”3

The nature of needing to remain covert yet effective requires ideology (transpose the concept onto corporate values and mission), but even more so efficient supply chain logistics and effective communication, not so far removed from the methods in which you might get groceries at your local supermarket (Shapiro, 2013, p. 249). Shapiro dispels the myth of insurgent “otherness” quite well with his assertion that:

The more we can see terrorists groups for what they are - ordinary organizations operating at a tremendous disadvantage. (Shapiro, 2013, p.3)

But surely there must be something that separates warfare and business. What about the assumption that all terrorists and insurgents hate whomever they are fighting, and that viewpoint is rampant throughout the organization? Myth, just as in how executive leadership and front-line workers see their role in the company and sector of the economy differently.

Agents in terrorist organizations often see the world differently than their leaders and tend to disagree with them on how best to serve the cause and how to carry out specific missions. (Shapiro, 2013, p.4)

It is the role of leaders to not only envision the desired end state, but to communicate this throughout the entire organization, and when subordinates challenge the myth, to not brush aside inquiry but ask why. What do they see that we don’t? Taking this line of questioning to an industry level - what myths do incumbent leaders and companies believe that allow disruptors to challenge what it takes to succeed?

Thanks to Shapiro we can determine at least a few aspects. Rather than seeing success as a combination of luck and opportunity, it’s utmost efficiency in the little mundane tasks involved in prepping the big move. It’s challenging the systems and being flexible in how you approach each problem you face. While it may be inefficient for some to not always adhere to a replicable method, it’s simply a strategic choice for other's, as Christensen discusses in the Harvard Business Review:

“The problem with conflating a disruptive innovation with any breakthrough that changes an industry’s competitive patterns is that different types of innovation require different strategic approaches. To put it another way, the lessons we’ve learned about succeeding as a disruptive innovator (or defending against a disruptive challenger) will not apply to every company in a shifting market.” (Christensen, 2015)

And herein lies the essence of Malkasian’s illusion of victory - Iraq post withdrawal was a shifting market. The same factors for success were not present post-withdrawel, and furthermore, the same strategy wouldn’t work in a more rural Afghanistan. There is no counterinsurgency doctrine that is universally applicable, as insurgent leaders in any other industry would be considered “disruptors,” returning to Christensen:

““Disruption” describes a process whereby a smaller company with fewer resources is able to successfully challenge established incumbent businesses … Entrants that prove disruptive begin by successfully targeting those overlooked segments, gaining a foothold by delivering more-suitable functionality—frequently at a lower price. Incumbents, chasing higher profitability in more-demanding segments, tend not to respond vigorously. Entrants then move upmarket, delivering the performance that incumbents’ mainstream customers require, while preserving the advantages that drove their early success. (Christiansen, 2015)

Change the wording, and you are not talking about Netflix or Uber taking on the video and taxi industries, you speak to the ways in which Al Qaeda or the Vietcong fought the United States. The nature of disruption in business is the way of the insurgent. It’s not in product, nor in sales. It’s in the mindset of the leaders.

“The term “disruptive innovation” is misleading when it is used to refer to a product or service at one fixed point, rather than to the evolution of that product or service over time” (Christiansen, 2015)

This is how leaders can succeed, by choosing process over procedure. When you choose the path of liminality over certainty, you lead teams that can disrupt, surivive, and thrive any change in mission or market. It is process, not procedure.

Underground or Insurgent, Media and Myth

This mindset is found anywhere you have leaders. In Compass Point 001, we discussed a rapper that has recently blown up on the international stage. Let’s look at an underground titan of the industry that has been around since the 1990s, selling millions of albums with his music features on TV, movies, video games, and sporitng events, collaborating with Lil Wayne Rage Against The Machine’s Serj Tankian, Kendrick Lamar, and Eminem, to name just a few out the over 400 guest appearences on his 22 studio albums.

Despite these accolade, Tech N9ne has stayed in the underground scene, yet to find” mainstream success” according to the traditional standards, having never been played on the radio or had a major label backing him. A native of Kansas City, Missouri, Tech N9ne started rapping as teenager, but never had luck with labels, and so started his own (Strange Music, partially inspired by the Doors song People are Strange) in 1999.

Where other artists relied on needing a big break, needing to impress a label in order to find success, Tech N9ne reframed how to succeed in the music industry by focusing on slow-growth longevity rather than viral hits. Each successive album release combined with better distribution partnership pushed Strange Music to sell hundreds of thousands more records as the years went on. Rather than renting studios, they built their own, custom-built for what their people needed to engineer success.

Tech N9ne continued this trend of self-relience with his co-founder and CEO of Strange Music Travis O’Guinn setting up smaller companies (Strange Headquarters (CEO, Accounting, Social Media, etc), StrangeLand (Recording Studio, Video, Soundstage), StrangeWorld (Merchandise Manfucturing, Order Fullfillment), StrangeWorks (Construction), even a car wash for their vehicles) to support Strange Music’s label acts, rather than outsource and rely on others. This allows for artists on Tech N9ne’s label (including himself) to have a consistent touring schedule, with the label having over 430 shows in 2018.4

It wasn’t the big viral hits that everyone remembered that lead to Tech N9ne having a net worth of around $20 million.

Strange Music succeeded where the Anbar Awakening failed. They didn’t rely on large infrastructure, a benefactor to keep them afloat. They decentralized their needs under a set of cells while maintaining control, all the while having buy in from their stakeholders. It wasn’t by looking at the industry not in the way which the established authority wants you to play. It wasn’t searching for the big wins. It was dedication, vision, and a process of managing the mundane.

Tech N9ne may be an outlier in his industry, but without question he is a model to follow. We have to ask ourselves as leaders, where do we start in envisioning operating against the myths we believe if it does not come naturally to us? Let us look to myth once again, but ones that are cautionary tales rather than executive narratives.

How Do We Foster Myth-breaking?

In Studio A24’s 2021 film The Green Knight, we are met with the character of Gawain, the nephew of King Arthur who has not become a knight. He is eager, overly so, to prove himself worthy of attaining the noble status. Young, impetous, he has internalized the narratives commonly found in Arthurian legend of chivalry and heroism, and what it means to be honorable.

When Gawain is presented with choices necessitating moral ambiguity, he begins to question his internal myths shaped by the expectations of the court’s external portrayel of honor, an illusion put out by societies expectations of “how to do things the the proper way.” His journey becomes one not of fullfilling these expectations, but rather one of self-understanding and validation. He needs to understand where he is lacking in order to strengthen his character.

The ending of the film subverts the traditional heroic ending trope of clear triumph. Leaving it more open ended for the audience to interpret Gawain’s journey of introspection regarding his life, we see the main character choosing to understand and accept himself, walking a different path rather than proving himself to others, something that Tech N9ne has discussed in multiple interviews.5 Ultimately, the story is not of grand accomplishments, but the manner in which one approaches life, the managing of the mundane.

Leadership Lessons

We’ve gone from the geopolitical framework down to the individual in an attempt to show you that myths are everywhere, and highly important - almost as much so as the people that perpetuate and believe in them. There are myriad lessons that can be transposed onto the work landscape of the 21st century amidst the rise of AI, remote work, and the creator economy.

As a leader, either in a role of authority or simply someone with influence - you get to choose if you believe the myths your organization operations under. You can only do that however, if you allow yourself to question the myths you hold about yourself, and how to achieve your dreams.

You always have a choice, there is always another way. To think otherwise is to accept the myth of permanence. Rather than focusing on your big wins and milestones, start by streamlining your everyday life, and that of your team. Build slow growth that will be resilient.

When you have a win, large or small, examine why you succeeded, rather than assuming, or confirming the answer you want to hear. Embrace the liminal growth that comes with uncertainty, and reconceptualize how to thrive. If you don’t the competition will.

Compassion is a term generally used for interpersonal relationships and social movements. Where you don’t hear it as often is in work environments, particularly in the realm of leadership development (regardless of industry, corporate or military), despite the scientific studies and business icons such as Bill George writing on it’s importance. What you do hear more often in those circles is “empathy.”

What’s the difference? Empathy and emotional intelligence are used to understand yourself, your team, etc., which then informs actions you can take or behavior you can check within yourself that will lead to a more positive environment.

They inform, but they do not call to action. In fact, it may be hard to take action if you are doing nothing but empathizing, because while yes, you are framing the situation in front of you in the manner in which the other person is interpreting it (i.e. feeling what they are feeling), you are simply sitting with them in that feeling. Leaders have an obligation to do more than just understand how someone is feeling and perceiving a situation.

Compassion is a step further than empathy, or perhaps a step back, a detached perspective. If you remember in Compass Point 001, I explained that liminal growth was like a river, and in order to keep growing you have to get back in the river.

Sympathy is seeing someone stranded on the riverbank with a broken canoe. Empathy is pulling off to sit with them and see how they are doing and how they got there. Compassion is helping them get back on the river and move forward towards their destination.

It is the desire to take action to help another. It can be as simple as stopping to help someone on the side of the road change a tire, or mentoring someone who could use your expertise and experience. It’s power lies in the ability to create massive culture shifts and movements, whether in company culture or on a societal level.

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A Value Where It is Least Discussed.

Compassion is an ancient concept for leaders, even if used by different terms. The Methods of the Ssu-Ma, one of the Seven Military Classics of Ancient China, has several passages that could be argued speak on compassion, one of which translates as the following:

“Neither contravening the seasons nor working the people to exhaustion is the means by which to love our people. Neither attacking a state in national mourning nor taking advantage of natural disasters is the means by which to love their people. Not mobilizing the army in either winter or summer is the means by which to love both your own people and the enemy’s people.” (Sawyer, 2007, p. 126).

What is worth noting here is the framing of the need to love your people, and to think of them in the planning phase of war. It admits the humanness of both your own people and “the enemy” whether combat or competition, and the need to understand what what state of mind they are in and relate it to who they are as a person. It’s not simply about being reactively compassionate, leadership requires proactive compassion.

You cannot contravene the seasons nor working the people to exhaustion. Let’s think about the wording - you cannot work against the seasons - the implication being that you cannot work against nature and its ebbs and flows.

This translates to a social context. People have seasons of their lives, and some experience changes in mentality during the changes of weather in different seasons - a tendency toward isolation and depression in winter is a common one.

Not having empathy for an individual or group and lacking compassion - pushing them to a point of burnout - does not show you care about the company. The company is made of people, not numbers.

Where Do We Lose Our Compassion?

The relevance of compassion during and and after war continues to this day, despite our tendency now to fight (or work) year round. We fight now just in wars, but in our day to day lives. Many segments of the economy rely now on service delivery over physical labor - and yet our minds still interpret the world at a neurological level the same as our ancestors did. Our civilization however, is no longer set up that way, making compassion hard to foster at times.

I’ve had the distinct pleasure of meeting journalist, author, and filmmaker Sebastian Junger, who in his book Tribe: On Homecoming and Belonging, explores how increasingly in modern society we find it hard to connect with one another, particularly in light of the dissonance we face living in relative comfort to our ancestors and tribal societies, yet still facing traumatic events while searching for meaning.

“As societies become more affluent they tend to require more rather than less, time and commitment by the individual, and it’s possible that many people feel that affluence and safety simply aren’t a good trade for freedom” (Junger, 2016, p. 16).

“Modern Society seems to emphasize extrinsic values over intrinsic ones, and as a result, mental health issues refuse to decline with growing wealth.” (Ibid, p. 22)

The post-pandemic work environment has turned into a battlefield of sorts with shutdowns and isolation affecting employee’s perceptions on workers rights and preferences versus corporate control. People are quitting jobs because they have been pushed to a point where the paycheck alone is not enough for their time and commitment. They ache for a return to meaning and authenticity in their life, found in community, in connecting all aspects of their life. To borrow a phrase from , we are seeking to rediscover “work-life integration.”

In organizations with a positive culture compassion is a key part of leadership. It is the reciprocal act of trusting those around you. In company cultures with toxic environments, the distinct lack of compassion pushes workers become similar to the veterans that fight demons after a war.

Isolated, unable to connect, and focusing on themselves.

The way out is seeing the human connection we all share. Compassion is a character trait of leaders that intrinsically drives you to look beyond your needs, beyond those of the company, to the needs of your people. It is an investment in organizational cohesion.

How Do We Cultivate Compassion?

Despite being a trait that is oriented towards others, compassion starts with the self. If you aren’t compassionate to yourself, you live vicariously through your compassion to others. It’s a form of personal reflection that must be developed.

The movie Everything Everywhere All At Once is an excellent representation of the development of compassion within a person. Evelyn Wang, played brilliantly by Michelle Yeoh, is initially dismissive towards her daughter’s needs and wants as she manages a failing business amidst forgotten dreams of how her life could have been. Except they aren’t forgotten - they are buried deep inside Evelyn, and they manifest as resentment, insecurity, and a low frustration threshhold. She is not compassionate towards herself.

Evelyn has very little empathy let alone compassion for members of her family, and the crux of the movie centers on the relationship with her daughter, Joy and how the disconnect between them lead to a multi-verse threatening series of events. Through seeing the different versions of herself and her family, Evelyn slowly begins to understand that in a large part the issues her and her family faces stem from her biases and self-imposed limitations. Perspective is what allows her to begin to empathize with those around her.

But as explained earlier, compassion is a step beyond empathy. The turning point in the movie for Evelyn is when she encounters a version of her daughter that is utterly nihilistic and almost convinces her that nothing really matters - the infamous “everything bagel scene" which ScreenRant correctly analyzes as “a direct metaphor for the overwhelming nature of modern society,” that we discussed earlier with Junger’s work Tribe.

Instead, Evelyn chooses to continue the fight for connection and ultimately stands up for herself, and in doing so stands up for her daughter. Finally able to cast aside her demons, she shows compassion to those around her.

The way to cultivate compassion starts with looking internally to the things that you as an individual, or a leader, do not like about yourself. Look for what which you try to hide or ignore - and then - embrace it. That doesn’t mean you have to accept it and never move on. Quite the opposite. Remember - compassion goes beyond the embrace of empathy and requires action. And if you are navigating the liminal growth river on a raft of broken canoes, you aren’t very capable of showing compassion to others.

The ability to have compassion is essential for leaders. We cannot hope to achieve thriving communities and organizations without it. Beyond causes, and beyond individual moments, you need to see how everything in their social ecosystem is linked in order to practice compassionate leadership.

You are the center of your ecosystem, but it does not revolve around you. So help it thrive, and it will help you thrive.

Leadership is rooted not in inherent ability, a set of learnable strategies or tactics, nor a role, or an art, or a science.

It could be argued that all of the above play a part in developing exceptional leaders, but even then what differentiates good leaders from exceptional is awareness of self and awareness of the “selves” of those they lead.

Leadership is found in perspective, and the ability to act upon seeing it’s intersections, but not in holding to one over another unless it is the right course forward. It is a semi permanent state of being at the borderlands of social groups and personal identity, responsibility and self-care, a liminal space, uncomfortable yet familiar.

The moment you step out of your comfort zone either as a new leader, a promoted leader with more responsibility, or even a longtime leader who is simply seeing the larger picture for the first time, you may question “who you are.”

A question struggled with by nearly everyone at some point in their life, it is especially true for those in charge of others or effecting change within themselves. Leadership is an epistemological revolving door, if framed in Taoist perspectives, liminality is our most natural state.

“Nature is not only spontaneity but nature in the state of constant flux and incessant transformation. This is the universal process that binds all things into one, equalizing all things and all opinions.” A Sourcebook in Chinese Philosophy, Wing-Tsit Chan.

Perhaps it is worth defining liminal states a bit further before diving into the leadership aspect. Liminality is an anthropological term originating from the Latin word for threshold, and refers to the state of in-betweenness one finds themselves in whether physical or mental.

It is the mental spaces that must be navigated for leadership to be cultivated in a person, and they can be just as unsettling as physical liminal spaces.

Think of the moments in time when you were unsure if you could accomplish something, but you went ahead and tried anyway. A time in which you didn’t feel like you fit in. You weren’t sure what a friend or significant other was thinking about you. You took a new role but didn’t feel like you knew what you were doing for 6 months. These are all examples of navigating liminality.

We experience liminality constantly, but it is imperative for leaders and those effecting change to embrace it rather than trying to move out of it. It starts with becoming comfortable in the self.

It’s possible to be in multiple and overlapping liminal spaces at the same time. When leaders get caught in the bottleneck of the hourglass, grains of knowledge erode and shape you pass back and forth between the intrinsic and extrinsic structures of self, they suffer what is commonly referred to as imposter syndrome, and burnout.

No longer part of the team, yet responsible for it. Required to understand the perspective of those who don’t necessarily understand the overarching vision and how they fit in, as well as why higher echelons of leadership aren’t willing to listen to them. True leaders see the entire ecosystem of the interconnected spaces they inhabit and how everything in it overlaps.

These liminal ecosystems and existences are everywhere. Perhaps the most commonly recognized are cross-functional teams, decentralized teams, sociopolitical identities, social media, insurgencies, and increasingly, AI.

Not only do we see and feel liminal space in our everyday lives, but we explore the concepts in our media and entertainment, depictions ranging from mental prisons and portal of horror to mystical places of transformation.

Perhaps the uncomfortability comes from it’s association with, or liminal spaces phenomenon on YouTube. Maybe it’s because as we become disconnected from each other in the digital age liminality is more visible.

Liminality, while always portrayed as unnerving, invites us to question what we know and critically think about how to navigate forward, an essential component of leadership. Our stories are rife with liminality being essential for one to triumph over insurmountable odds.

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We see this in Star Wars: Ahsoka, with The World between Worlds, a physical representation of liminality that exists outside time and space that allows for growth to happen. Similar to the interplay of our past experiences and traumas mixed with our dreams for the

It’s also seen in Stranger Things, with the the Upside Down, a mirror realm of our plane of existence with beings that torment and taunt us with the intent to control us and take over our world. Sound like intrusive thoughts, depression, and listening to the voices of your haters, doesn’t it? What must the protagonists do to stop the chaos from overtaking their world? They have to into the Upside Down itself, into the liminal space that terrifies them so, because only in that space can they defeat what breaks through to the surface and erodes the mindset of confident leaders.

The Studio Ghibli classic movie by Hayao Miyazaki, Spirited Away shows a less visually terrifying example of liminal spaces. Rooted in Shinto lore, the story centers around the perspective of a child separated from her parents. As Margarita from PlainFlavoredEnglish puts very eloquently:

“By purging her of her former identity and pushing her forward into a liminal state, Miyazaki does for Chihiro what she does for the characters she purges: helps her to confront the fear of emptiness that makes her so passive and helpless to begin with. Only then can she really recognize that she is not empty or helpless at all.”

Notice that in all these stories if the heroes are not receptive to growth, the darkness that dwells in liminality triumphs, and it is only with intentionally going into liminal spaces that it is defeated. Navigation via perspective of the liminal space is a requirement for growth, both for the individual leader and their team.

Liminality overlaps these stories with the real world as well. The viral explosion of artist Hanumankind (real name Sooraj Cherukat) onto the global rap scene with his song Big Dawgs in the past few weeks shows liminality in multiple ways. An Indian born son of an oil industry worker, Cherukat spent years abroad with formative years spent in Texas, the rap styles of the southern U.S. heavily influencing his sound.

Moving back to India where he has resided now for 12 years, the liminal state he finds himself successfully navigating is one of cultures and musical sound. A clear leader in the south Indian rap scene (now global), this is only possible through pressing forward through liminality by believing in his artistic identity that encompasses all of his experiences.

While successful at showcasing his identity with confidence, his journey hasn’t been without struggles, seen in other songs such as Go To Sleep as well as interviews showcase how Cherukat has navigated the intrinsic and extrinsic struggles of multi-cultural liminal spaces.

In a completely different industry, Professor of Governmental and International Affairs Gerard Toal talks about liminal spaces in his book The Near Abroad, but rather than explicitly discussing liminality this discussion centers on the geo-political discourse and culture shock felt by the member states of the former Soviet Union, where even to this day countries that border Russia experience liminal states of existence and identity which leads to international conflict. The macro-liminality can be narrowed back down to the micro of individual leaders with Toal’s assertion that:

“Aspirational and ideal visions of [world order] how things ‘ought to be’ in the abstract without references to constraints and necessary compromises.” (Toal, 2017).

These images, or levels of ecosystem analysis, of the self, the team, and the world show that in order to be a leader, we must learn to navigate the liminal spaces, not run from them.

We beg to be told how to do this, or to at the very least ease our discomfort by sharing this state of disconnect that connects us all. Perhaps it is because this liminal state is at the core of our societal processes that politics and war intertwine to create uncertainty like no other. It is so much easier for leaders to become entrenched in their ways and not consider another path towards meeting ones goals, yet if one continues to hop out of the river because they are uncomfortable with swimming, they won’t get very far upstream.

Your perception of self is not distinct from that of your perception of you are a leader. You are defined not by who you were or are, but who you are as a process, and how well that process embraces and navigates liminality.

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Compass Points: We all need a direction to go in, especially when trying to grow personally and professionally. This series is a reflection on a lesson or concept I've thought about the previous week that helps you readjust or maintain the direction going forward by enhancing your perspective of your ecosystem.

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