The Pathway to Breakthrough

How do you generate real insight for jumping to the next level of disruptive business excellence?

James Milo
16 min readJul 29, 2019

“The most thought-provoking thing in our thought-provoking time is that we are still not thinking.”

Martin Heidegger

Are you constantly vexed by people challenges while introducing new business processes, changing organizational structure or shifting entrenched culture within an enterprise? Then what I call “World Design” will prove extraordinarily powerful in advancing your leadership goals and creating breakthrough results.

Embedded in what follows below, there are more than a dozen core insights you can discover and deploy almost immediately. If you contact me with 3 or more of them, I will show you in a half-hour session how to implement their power (plus the ones you may have missed) on stubborn problems confronting your enterprise.

Regardless of industry, sector or company-size, the practice of World Design is central to being relevant, competitive and adaptive in a continually changing marketplace. Since World Design draws on the spirit of what is esoterically named Philosophical Engineering, let me first explain this curious term before you mistakenly dismiss it as surely an oxymoron.

Physics was once known as “Experimental Philosophy.” Following Tim Berners-Lee, widely acclaimed as the inventor of the World Wide Web, the discipline of Philosophical Engineering concerns itself with the practice of defining a new world and how it works.

In philosophy, ontology is the formal study of being. In computer science and information science, an ontology is a set of entities (objects, ideas, events) and categories in a subject area or domain that shows their properties and the relations between them. Philosophical Engineering specifies what exists in a world along with the protocols and languages that determine how those entities interact (behave) and communicate, respectively, according to agreed rules.

For example, the world of the Web has been designed to contain objects such as web pages with URIs (Uniform Resource Indicators, previously Locators), protocols like HTTP (HyperText Transfer Protocol), and languages such as HTML (HyperText Markup Language). These components have constituted the carefully evolved building blocks of the Web for more than two decades. In such a scheme, the Web itself can be considered (abstractly) as the space of all URIs.

We are not analyzing a world, we are building it. We are not experimental philosophers, we are philosophical engineers.

— Tim Berners-Lee, Message to W3C Technical Architecture Group mailing list (2003)

Corporate leaders design and dwell in worlds invented for marketplace impact. Ensuring and optimizing that impact make up what might be termed being-in-business.

World Design is thus a crucial aspect of architecting successful ventures. What may be less obvious to the casual observer is the central importance of philosophy as a rigorous discipline with conceptual power for informing and guiding the effective design of a world.

While traditional psychology may enable explanations within an accepted box of current neurobehavioral theories, modern philosophy provides deep insight for shifting both thinking and action to create a whole new box at a different level.

Psychology is useful for an understanding of why we are stuck. Leaders, however, are tasked daily with taking pragmatic action and getting their teams unstuck fast. Knowing why you are trapped in a deep, dark hole may illuminate the sad predicament (and even keep you stuck) but it does not create the empowering ladder to let you escape.

To introduce compelling and powerful options that allow you to resolve long-standing organizational issues and perplexing marketplace challenges, we need to revolutionize not only the way we think about business excellence but also thinking itself. In turn, this requires deftly confronting conventional models that are fast running out of steam in a complex, digital economy as well as challenging our most cherished assumptions and traditional views about what constitutes being a person and having a world in which to act.

Among the preeminent thinkers worth studying in depth for radical insights and incisive questions about human being along with the notion and nuance of world, Ludwig Wittgenstein and Martin Heidegger stand out as the most intriguing and fascinating of twentieth-century philosophers.

The adoption and application of their work to the world of business is an unexplored territory for most leaders. The dividends, however, are profound for those seeking new ways to observe and design systems that enable reinventing leadership and generating organizational transformation.

My work with C-Suite executives is grounded in the work of such genius which I have appropriated and translated for action by we mere mortals on Monday morning. The results are rapid, reliable and rewarding across both personal and professional domains in organizational change efforts at scale.

Any effort to provide an in-depth interpretation of either man’s work is, however, fraught with complexities, not least of which derive from Heidegger’s and Wittgenstein’s highly individual ways of thinking and writing.

Both Wittgenstein and Heidegger present a tough, if not impenetrable, read for first-time students. Despair not, however, since you do not have to become a scholar fluent in arcane literature but you will benefit greatly as a leader by learning some key strategic moves so you can think with Wittgenstein and Heidegger.

Let’s take Wittgenstein’s famous Logisch-Philosophische Abhandlung (1921), published in English as Tractatus Logico-Philosophicus (1922). Ostensibly a work dealing with ontology and formal logic, the Tractatus also concerns ethics as Wittgenstein revealed in the following passage from a letter written to a colleague:

“The book’s point is ethical. I once meant to include in the preface a sentence which is not in fact there now, but which I will write out for you here, because it will perhaps be a key for you. What I meant to write then was this: my work consists of two parts: the one presented here plus all that I have not written. And it is precisely this second part that is the important one. For the ethical gets its limit drawn from the inside, as it were, by my book; and I am convinced that this is the only rigorous way of drawing that limit.”

The passage above contains a tantalizing but almost buried clue about breakthrough. What is not written, what is not there, does, indeed, also turn out to be the most important part for creating genuine breakthroughs, not only in the halls of higher education but also the super-highways of the digital economy.

Breakthroughs are at the heart of any serious innovation, and especially transformation—a word much abused by marketers who conflate it with ordinary change. The central task of Transformation — as a genuine discipline in its own right—is not to find new knowledge and powerful theories about the world as do the various branches of science, but rather to examine and understand what is deeply presupposed and most taken for granted in any such search. As Heidegger tells us:

“to philosophize means to be entirely and constantly troubled by and immediately sensitive to the complete enigma of things that common sense considers self-evident and unquestionable.”

If the self-evident does not permit questioning then it stands permanently impenetrable and immune to any change. Only with serious inquiry guided by deep curiosity, even awe, will the “tranquilized obviousness” of the self-evident be dispelled.

In the perpetual headlong rush to produce results, adults often forget to question and, worse, forget they have forgotten. What gets produced in this accepted but mindless haste is then inevitably an incremental commodity of mere productivity and not a high-value gift of original creativity for disruptive innovation.

The famous analytic philosopher, Bertrand Russell, tells the story of a tortured, young man who brought him a burning question: “Will you please tell me whether I am a complete idiot or not? If I am a complete idiot, I shall become an aeronaut; but, if not, I shall become a philosopher.” Russell, not knowing if the student was merely an eccentric or perhaps a genius, assigned a special writing project about a tricky philosophical subject to be tackled over a short school break. “After reading only one sentence,” recalls Russell, “I said to him, ‘No, you must not become an aeronaut.’ And he didn’t.” That student then made a next-level jump into philosophy and became the thinker we now know as Wittgenstein.

Wittgenstein’s philosophical acumen was demonstrated in short order through his novel and unusual solutions to cutting-edge problems in logic. Throughout his life, he jumped in and out of philosophy, eventually sourcing notes for three very different landmark books, each hailed as remarkable breakthroughs.

The Tractatus, completed while Wittgenstein served in the trenches of the eastern front of World War I, was presented as a solution to all the significant problems of logic and philosophy. Believing his work was done, Wittgenstein duly exited academia only later to jump back in as he realized the fundamental mistakes in his thinking. For the next 20 years he confronted a growing conviction that a proper understanding of language, not logic, would expose the hidden flaws in philosophical reasoning.

With the posthumous publication of Philosophical Investigations, and the repudiation of many of the central claims of the Tractatus, Wittgenstein became famous for revolutionizing philosophy not once but twice. In the Tractatus, logic is given the central role of determining the structure of language and reality, and presents a rigidly structured world amenable to explicit representation and direct analysis. By contrast, Philosophical Investigations admits a far more modest conception of a complex world that resists any simple articulation that obscures the invisible but pivotal role of context.

With the addition of a third major work, On Certainty, Wittgenstein further cemented his uncanny knack for jumping from problem-solving to problem-dissolving. What plagues us is not lack of analytic solutions but confusion in our thinking about the original problem itself.

Abstracting an idea from the context of its everyday use (where we demonstrate our knowing through the practices we employ) causes all sorts of mischief and Wittgenstein teaches us to be vigilant about the use of language in order to avoid perplexing and needless confusion.

Wittgenstein was a warrior for breakthrough insights about the most fundamental issues. Such insights are breaks with, or jumps from, previously limited, or even erroneous, unchallenged conceptions to far more fruitful interpretations that prove useful in completely unexpected and surprising ways.

Wittgenstein viewed philosophy as an investigative activity and not a comprehensive body of doctrinal positions and theories. Adopting this anti-theoretical stance, he saw gaining penetrating clarity on foundational issues as the route to escaping fundamental errors that kept efforts stuck with confusions and thus prevented real advances.

Wherever you are repeatedly stuck, there may be a key confusion that condemns any action on your part, from the very outset, to inevitable failure. What possibilities (ideas, distinctions, practices, frames) are you missing that would allow you to jump to a new level of effectiveness? Following Wittgenstein’s lead, the place to look may be at the very foundations of what you are doing.

For example, leadership development is a recurrent problem for many organizations. Traditional theories of leadership that underpin standard training efforts stem from a behavioral psychology frame.

Could that frame actually be keeping the problem of generating genuine leadership from being handled decisively? If so, what’s the elusive insight we need to effect the “jump” from better management to true leadership?

In Philosophical Investigations, Wittgenstein introduces the concept of language-game (German: Sprachspiel). He observes that “…the speaking of language is part of an activity, or a form of life” through which language gets its meaning.

Wittgenstein held that a word or even a sentence has meaning as a result of the “rule” of the “game” being played in a specific form of life. Depending on the context, for example, the utterance “Love all!” could be an edict by a spiritual minister, a new age answer to a question about how to resolve race relations, or the score in a tennis match.

The meaning of a knight in the game of chess is not determined by specifying the material from which the piece is made. You must follow the peculiar moves or “jumps” that can be made with a knight and the rules it is governed by. In the world of chess, knight is not the name of a piece of ivory, but a function within a context of rules for the game.

What if being a leader has little to do with doing so-called “leadership behaviors” and is far more about the introduction and combining of missing possibilities that leaders inject through language to disclose new worlds of opportunity and challenge that energize followers? Leadership would then open itself to being intelligible as a dynamic language-game and not a static set of behaviors to be identified and drilled.

Now take a look at the remarkable photo below. Why is this snapshot in time so powerfully beautiful? The atmosphere of haunting stillness is deeply accentuated by the empty bench. The marked absence of any person magnifies the fog-swept presence of nature. Absence unconceals presence.

Photo courtesy of Aaron Strout

What an entity “is” depends on the conditions that allow it to manifest itself as itself. This concept, called “unconcealment” or disclosure, is central to Heideggerian thinking.

The condition of possibility for an entity to manifest itself is the existence of a world or a sociocultural, historical context we inhabit (e.g. the world of sports, the world of medicine, etc.)

Such a world is itself disclosed and Heidegger held there have been a number of distinct worlds that have emerged and disappeared in history.

One very special kind of disclosure in the corporate journey of disruptive reinvention of a marketplace is the emergence of a breakthrough: a sudden, dramatic, and important discovery or development.

Key breakthroughs are often hailed as “paradigm shifts.” A paradigm, or prevailing framework, is an interconnected matrix of basic concepts and accepted practices that determine (limit) how things are viewed, said and done. A paradigm shift is a fundamental change in that network of meanings and methods.

Major paradigm shifts almost always involve escaping from a useful but constraining framework of thinking about reality itself. Such “jumps” are radical leaps into a territory that is not there (at least from the perspective afforded by the old paradigm) and so, for the perplexed onlooker, often appear to verge on the mystical and simply “unsayable.”

Iconic designers are famous for masterfully bringing into being entirely new artifacts that improve life, often in multiple dimensions. But despite the best analytic efforts of the so-called “Design Thinking” movement, breakthrough creativity for genuine innovation is not mere iterative prototyping informed by empathic understanding. Far beyond classic “creative problem solving” tricks and techniques for groups, such creativity is an inspired quantum leap from one idea space into another. And the less adjacent those two idea spaces are, the bigger the breakthrough.

The capacity to “jump” (or Join Unique Missing Possibilities) derives from the generation of a “powerset” that not only can be learned by individuals but it can also be scaled across an entire organization to ensure sustained success.

In mathematics, the powerset of a set S is the set of all S’s subsets. (The elements of a powerset are always themselves sets, because each element is a subset of S.)

The diagram of the lattice for a powerset P({a, b, c}) is shown as:

In SWIFT, a new technology for transformation that underlies the executive education programs offered at KnowledgePassion, Inc., we use the term “powerset” to denote the ENTIRE set of interactive combinations across a leader’s mindset, thoughtset AND skillset.

Given that we are now in an age of Artificial Intelligence, Blockchain and other rapidly emerging technologies that will either transform or replace existing jobs, it is vital to understand that skillsets emerge from embodied “thoughtsets.”

While a “mindset” is generally recognized to be a colloquial name for an encompassing attitude or mood that pervades action, a “thoughtset” is a core collection of ideas, concepts and accepted practices for achieving a specific goal. To the degree that your thoughtset on a particular thorny issue or business challenge is limited to traditional thinking and approaches, your creativity for innovation is severely hampered.

The condition for the possibility of a “jump” —a disruptive but empowering launch into the valuable unknown—is the development of courageous optimism for adventure girded with a deep willingness to learn how to learn.

Following the lead of creative artists, achieving a jump is best done through a highly experiential process that confronts individuals with personally meaningful challenges just outside their current proficiencies. As participants grapple with failure, they come to see the limits of workability in their current powerset. Then they open themselves to jump, not to make something, but to make something possible.

Helping engaged players build self-efficacy in situations that previously were held to be next-to-impossible releases enormous amounts of latent energy and ignites ambition. The transformation of identity felt as the result of a serious jump is both deeply empowering and life-changing.

Paradoxically, in order to transcend the seemingly impossible, truly disruptive twenty-first century experts “jump” by learning how to think what cannot be thought and doing what cannot be done. What cannot be thought is obscured by the sheer blindness of the current paradigm and what cannot be done is behavior disallowed by the current paradigm. These artificial limits simply disappear in the wake of the new framework afforded by the joint combination of imagination and intention to be a leader and take the jump.

As a phenomenon, transformation is not simply the cosmetics of bold change writ large. If it were then the failure rate of digital transformation projects would not be the current 70% or more.

Possibility as a domain of inquiry is a space of ideas, each of which is a possibility. (We denote the domain with a capital P and its constitutive elements with a lower case p.)

Transformation is a shift in the space of Possibility. It occurs for an individual, team or entire organization when what is abstract and only “theoretically possible” moves into the concrete, real and immediate personally possible. The crucial move from “well, I guess anything might be possible” to “I know this is possible for me” is decisive and energizing for action.

A world opens to you (becomes disclosed) when the possibilities it affords become possibilities (unconcealed) for you. As a dynamic result, a new possible future emerges from which there is no turning back.

World Design is the singular task of effective leadership that enrolls engaged participation. The future occurs to followers as not only meaningful and worthwhile but also theirs.

Where leaders fail to appreciate that a serious jump involves crossing a mental Rubicon by almost everyone in the organization, transformational efforts inevitably flub. In this sense, all effective transformation is personal.

Breakthrough transformation is the transmutation of Impossibility into Possibility. This occurs, in part, through a “jump” that brings forth (makes present) absent or missing possibilities and then combines them to create uniquely valuable present possibilities that liberate positive energy and generate palpable opportunity. When your future changes, your experience of the present shifts too. In essence, your entire world changes and it occurs to you very differently.

Such an interpretation also suggests that a new Design Thinking might be “rewritten” as Dasein Thinking where Dasein is a German word that literally means “being there” or “presence” (German: da “there”; sein “being”).

This particular jump incorporates escaping the Cartesian paradigm of interpreting our human being as a detached subject observing a separate and distinct objective world. In eschewing this “abstract agent” view, Heidegger held Dasein to be that “entity which each of us is himself” and “which in its being has this very being as an issue.” Moreover, in stark contrast to a Cartesian paradigm, Heidegger saw Dasein as “always already” (inescapably and immediately) being in practical engagement with one’s environment and thus having an integral coherence as being-in-the-world where a never-ending process of involvement with the world is mediated through projects that reflect care and concern.

In this Heideggerian interpretation where Dasein is revealed by projection into, and engagement with, a world, the term “empathy” comes to have a very different meaning and purpose than what is espoused in typical half-day corporate workshops on ordinary Design Thinking. Such programs are typically run by professional trainers who do not realize their own schooling and subsequent instructional efforts are drenched in Cartesian Metaphysics. This has serious ramifications for practice.

For example, ordinary Design Thinking deploys empathy as a useful front-end tool by which we gain access to the “inner life” of so-called “end users“ and what their unexpressed or hidden requirements may be. In a Heideggerian Design Thinking, or what might be termed Dasein Thinking, empathy reveals an entire world of engaged projects and networked concerns while simultaneously opening the missing possibility of an authentic being with others. In SWIFT we call this world listening and it is fundamental to World Design.

As vociferous design leaders and professionals have insisted, being a designer is not doing design thinking. Designers disclose Possibility.

They bring forth new worlds of opportunity embodied in artifacts that surprise and delight. It is no accident that Steve Jobs, one of the greatest business designers of all time, proclaimed:

“…it’s really hard to design products by focus groups. A lot of times, people don’t know what they want until you show it to them.”

Advocates of current Design Thinking, extol its virtues as stemming from being “human-centered” but the foundational inquiry of what it means to be a human being, much less the meaning of being, is entirely absent.

This blindness condemns ordinary Design Thinking as a movement to be reduced and implemented as yet another corporate program in a long line of “quick fixes” for the imperative of innovation.

Let’s jump from using “design” as a noun to employing, instead, its full power as a verb in the phrase “Design Thinking”—enabling with primordial purpose the active reinvention of thinking wherever it is applied for our collective benefit and satisfaction. (Along these lines see Heidegger’s Was heißt Denken? [What is Called Thinking? or What Calls for Thinking?], a profound meditation on engagement with thought within an ontological frame where thinking moves beyond instrumental rationality and calculative reasoning to meet thanking.)

Dasein Thinking promises a further reframing jump for the emergence of truly being a designer disclosing new worlds through creating a radical opening for the possibility of generating transformation and not simply cranking out better products, services or experiences.

Here’s a sample exercise for initiating a jump. It will be particularly powerful for those who fully appreciate the urgency of transformation in their industry and are keenly interested in beating the bleak odds of success for such an ambitious undertaking. This tricky reflection is an invitation to insight with deeply practical implications.

Consider anew what’s missing or, better, hidden in plain sight, in the following phrases: being a leader, being in business, being a team.

Reducing the meaning of any or all of these phrases to doing identified key activities optimized for analytic efficiency and effectiveness betrays the very blindness that guarantees why efforts at transformation fail so often. Really want to beat the dismal odds of success? You’ll need to jump to a whole new level of appreciation of what it means to be.

Here’s a hint: While any particular Dasein is absent in our featured photo above (and thus is a missing possibility), the presence of the bench, as an object designed by Dasein for taking care of sitting comfortably in the woods, helps us better experience the unconcealed being of nature … and perhaps even being itself.

This article is the first in a series. Next up: The Power of Invisibility.

The MILO Process is an experiential off-site designed to trigger multiple levels of transformative insight for executive teams grappling with thorny organizational challenges surrounding leadership, innovation and marketplace performance. Using an immersive, design studio format, we explore issues in depth to confront the fundamental changes needed to dynamite logjams and create breakthrough results.

The MILO Process employs frameworks and principles from SWIFTa leading-edge technology for creativity and innovation containing both strategic methods and tactical tools for generating insight. To learn more about how to create the radical shift to ultra high performance, please contact me for a confidential briefing.

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James Milo

Milo is the founder and Chief Education Officer of KnowledgePassion, Inc. Connect with him at