Part three in a series. The reading list came from a comedy song; the parallels came from a conversation with Claude.
The first two essays in this series wrote themselves. The Prince had been on my shelves since university; The Art of War was a book I had read more than once as well. When I drew parallels between those works and the ITIL guiding principles, I was working from familiar material.
For a third essay, the obvious classical thinkers were used up. The candidates a colleague might suggest, Aristotle, Confucius, and Marcus Aurelius, each had genuine merit. None had the quality I wanted: a single thread that could carry an entire essay, the way governance carried Machiavelli and competition carried Sun Tzu.
So I tried something different. I asked Claude, an AI assistant, to find the parallels for me. Not from a single thinker, but from a list I would not have chosen on my own: the fourteen philosophers named in Monty Python’s “Philosophers’ Drinking Song.”
I should be honest about this. I have read Machiavelli. I have read Sun Tzu. The closest I have come to the philosophers in this essay is the song that inspired it. Kant, Heidegger, Hume, Schopenhauer, Hegel, Wittgenstein, Schlegel, Nietzsche, Socrates, Mill, Plato, Aristotle, Hobbes, and Descartes are names I know from the Bruces sketch, in which a faculty of Australian philosophy professors all named Bruce sing about the drinking habits of their illustrious predecessors. I am not specifically familiar with any of their works, beyond having clearly negative impressions of some of the opinions espoused by Kant.
So this is a different kind of essay. I asked Claude to map all fourteen philosophers, two to each of ITIL’s seven guiding principles, and to summarize each contribution in language a service manager could use. What follows is a curated version of that exercise. I have edited the prose, sanity-checked the philosophical claims where I could, and removed the parallels that did not survive scrutiny. The mapping itself is the AI’s, the prose around it is mine, and the cheerful absurdity is shared between Monty Python, an LLM, and a man who definitely should have read Plato and Socrates by now.
The question I started with is the question that matters: would the parallels still hold when the reading list was, on its face, ridiculous? The ITIL guiding principles (Focus on Value, Start Where You Are, Progress Iteratively with Feedback, Collaborate and Promote Visibility, Think and Work Holistically, Keep It Simple and Practical, and Optimize and Automate) have remained unchanged from ITIL 4 (2019) to ITIL 5 (2026). Here is how the fourteen philosophers matched with them.
1. Focus on Value
ITIL: Every activity must link back to stakeholder value
ITIL’s first guiding principle holds that every activity an organization undertakes should map back to value for the organization, its customers, and its stakeholders. Value is subjective, defined by the consumer, and must be continuously understood and validated.
John Stuart Mill on what counts
Mill’s utilitarianism is the most direct philosophical statement of “Focus on Value” ever written. The right action, Mill argues, is the one that yields the greatest good for the greatest number. For Mill, value is defined by its effect on those it touches, not by the intentions of those who produce it. He insists on hierarchies of value: not all goods are equal. The distinction between higher and lower pleasures is the same distinction service managers make every day between work that builds capability and work that merely fills the day.
Friedrich Nietzsche on whose values
Nietzsche poses the harder question Mill cannot answer. Mill assumes we know what counts as valuable; Nietzsche asks who decides, and on whose authority. His project of the revaluation of all values is a warning against inheriting definitions of worth from custom, convenience, or vendor PowerPoint slides. For an IT organization, Nietzsche’s challenge is uncomfortably practical: are you measuring value as stakeholders define it, or as tooling and incentives find it convenient to define?
What a service manager takes from both
ITIL’s framing of value as subjective and defined by the consumer is Nietzsche’s question answered by Mill’s method. The combination should make any leader uneasy, because most service organizations measure what is easy to count, not what stakeholders need most, and most inherit a definition of value rather than choosing one deliberately.
2. Start Where You Are
ITIL: Assess the current state honestly before building something new
ITIL warns against the temptation to rebuild from scratch. Instead, assess existing services, processes, people, and tools objectively. Use measurement and direct observation to determine what works and what can be reused, repurposed, or improved.
Socrates on self-knowledge
The Delphic instruction Socrates made his life’s work was “know thyself,” and he meant it ruthlessly. The cost of self-deception, in Socrates’ world, is not embarrassment but the entire collapse of any subsequent reasoning. Apply this to an IT organization: every assessment built on flattering reports, every roadmap built on aspirational capability claims, every transformation plan that ignores what people actually do day to day is, in Socrates’ terms, founded on ignorance. Socrates would tell you the assessment itself, however uncomfortable, is the work.
David Hume on what you can claim to know
Hume is the great empiricist skeptic. He refuses to grant abstract reasoning any authority that experience cannot confirm. For Hume, what you observe is your only legitimate starting point; what you infer beyond observation is, in his unsparing terms, “fit only for the flames.” The IT leader who builds elaborate plans on what should be true, rather than what is observably true, is making the error Hume diagnosed in metaphysicians.
What a service manager takes from both
Socrates and Hume converge on a single instruction: look honestly at the organization, not as you wish it were, and believe only what the evidence supports. ITIL’s “Start Where You Are” is the operational version of that instruction. Both philosophers also warn against the opposite mistake (Descartes’ mistake, as we will see) of throwing everything out and starting from a presumed clean slate. Reality is rarely as clean as the slate.
3. Progress Iteratively with Feedback
ITIL: Break work into manageable iterations and use feedback to stay aligned
ITIL advises practitioners to break large initiatives into manageable iterations and use feedback loops to ensure each step remains aligned with evolving needs and changing circumstances.
Hegel on the dialectic
Hegel’s dialectic (thesis, antithesis, synthesis) is the most formal account of iterative progress in Western philosophy. For Hegel, progress is never linear and never one-shot. Every position generates its own contradiction, and the resolution of the contradiction yields a higher position which then generates its own contradiction in turn. The synthesis is not the end; it is the next thesis. ITIL’s iterative loops, where each cycle of work produces feedback that reshapes the next cycle, are dialectical progress in service-management clothing.
René Descartes on method
Descartes is here for an unexpected reason. His Discourse on Method lays out four rules: accept nothing as true that you do not clearly see to be so; divide each problem into parts; proceed from the simplest to the most complex; and review the whole frequently enough that nothing is omitted. Read those rules without their seventeenth-century framing and you have an iterative method with feedback loops. Modern Agile practitioners would recognize Descartes’ instruction to review the whole frequently as the retrospective. His insistence on dividing problems and starting simple is the case for small batches.
What a service manager takes from both
Hegel and Descartes both insist that progress is built up by iteration, not delivered in a single decisive stroke. The eighteen-month waterfall project assumes a Cartesian universe without Descartes’ fourth rule, the one about constant review. The fixed multi-year roadmap that resists revision assumes a Hegelian world that has stopped at Hegel’s first move. Both philosophers would tell you the only legitimate way forward is to take small steps, check whether you are still oriented correctly, and adjust.
4. Collaborate and Promote Visibility
ITIL: Information should flow openly and silos should fall
ITIL promotes open information sharing, cross-functional collaboration, and the elimination of hidden agendas. Organizational silos are recognized as one of the greatest threats to effective service management.
Wittgenstein on the impossibility of private meaning
In the Philosophical Investigations, Wittgenstein argues that there is no such thing as a private language. Meaning is constituted in shared use, in what he calls language games. A word that no one but you can interpret is not a word; it is a noise. Apply this to organizational knowledge: the runbook that lives only in one engineer’s head, the architecture decision that was never written down, the alert threshold that was tuned for reasons no one remembers. These are private languages in Wittgenstein’s sense, and they are not really knowledge at all. Knowledge no one else can use is functionally identical to no knowledge.
Hobbes on the necessity of common ground
Hobbes’ Leviathan describes the state of nature as a war of all against all, in which life is “solitary, poor, nasty, brutish, and short.” His remedy is the social contract, where individuals agree to make their commitments visible to each other and to a common authority that can enforce them. This is what an IT organization without shared visibility looks like: parallel teams optimizing for incompatible local objectives, each acting in good faith, each producing collective harm. Hobbes would advise you to make commitments visible and explicit, because covenants without the sword are but words.
What a service manager takes from both
Wittgenstein tells you that information hoarded is information lost, because meaning that cannot be shared is not meaning. Hobbes tells you that without shared visibility, individual rationality compounds into collective dysfunction. ITIL’s insistence on transparency and the elimination of silos addresses the same diagnosis from two different directions.
5. Think and Work Holistically
ITIL: No service stands alone
ITIL emphasizes that results are delivered through the effective integration of multiple dimensions: people, technology, partners, and processes. Optimizing one area at the expense of others degrades the entire system.
Heidegger on the world as context
Heidegger’s most useful contribution for the IT leader is the concept of being-in-the-world. Nothing, Heidegger argues, is intelligible in isolation. A hammer is not really a hammer apart from the workshop, the carpenter, the wood, and the building under construction. Pull it out of that context and it becomes a curious metal-and-wood object whose purpose is opaque. The same applies to a service. Considered as a standalone artifact, the service is a configuration of code and infrastructure. Considered in its context (the user’s task, the business outcome, the technological ecosystem, the regulatory environment), it becomes the actual thing it is. Most IT failures are failures to see the whole context in which a service does or does not work.
Schlegel on the fragment and the whole
Schlegel is the wild card on this list, the early Romantic critic whose central insight was about the relationship between the part and the whole. For Schlegel, the fragment is interesting only because it gestures at a totality it cannot contain. He famously wrote that a true fragment “must be entirely isolated from the surrounding world and complete in itself, like a hedgehog.” A service is exactly such a fragment. It must be separable enough to be operated, observed, and improved on its own; it must also be aware of the totality it serves. An IT organization that sees only the fragments is making Schlegel’s mistake; one that sees only the totality is making the opposite mistake.
What a service manager takes from both
Both philosophers insist that meaning is a property of the whole, not the parts. ITIL’s four dimensions of service management are an attempt to ensure no single part is mistaken for the whole. Heidegger and Schlegel would both approve.
6. Keep It Simple and Practical
ITIL: Use the minimum necessary steps
ITIL advises practitioners to use the minimum number of steps necessary, eliminate processes that do not add value, and apply outcome-based thinking to produce practical solutions.
Aristotle on practical wisdom
Aristotle’s concept of phronesis, practical wisdom, is the disposition to do the right thing in the right way at the right time. It is not knowledge of universal rules; it is the trained capacity to recognize what a particular situation calls for. His golden mean instructs that virtue lies between excess and deficiency: too much ceremony in a process is a vice, too little discipline is also a vice, and the practical art is finding the point between them. ITIL’s “minimum number of steps necessary” is Aristotle’s mean applied to the design of a process.
Schopenhauer on simple writing
Schopenhauer’s essay “On Authorship and Style” is one of the most savage attacks on academic obscurity ever written. His charge: writers who hide simple ideas behind complex sentences do so to disguise the absence of thought. “Anyone who has anything to say is the more easily understood for using simple language.” Schopenhauer would treat an over-elaborated ITIL process the way he treated an over-elaborated philosophical paragraph: as evidence that someone is concealing the fact that they do not really know what they are doing. If the process cannot be explained simply, the simplification has not been done yet.
What a service manager takes from both
Aristotle tells you the right amount of process is a matter of practical judgment, not universal rules. Schopenhauer tells you that complexity for its own sake is almost always a tell, a sign that someone has not done the harder work of finding what the situation actually needs. The seventeen-step change-approval process for a routine patch fails on both counts: it violates Aristotle’s mean and offends Schopenhauer’s prose standards.
7. Optimize and Automate
ITIL: Eliminate waste and let technology do the routine
ITIL instructs organizations to eliminate waste, deploy human resources where they add genuine value, and automate everything technology can handle more efficiently.
Plato on the well-ordered system
Plato’s Republic argues that the well-governed state is one in which decisions flow from a clear hierarchy of knowledge, with the wisest at the top and execution descending through trained, predictable layers. Stripped of Plato’s elitism, the structural insight is sound: when the rules are right, individual decisions become routine. The Forms function in his metaphysics as the templates from which particular things derive their character; in modern infrastructure terms, they are the platforms, the standards, the well-designed defaults. A platform that handles the routine automatically is a Platonic form expressed in code. The work goes into building the form; once built, the instances follow.
Kant on the universalizable maxim
Kant’s categorical imperative tells you to act only on that maxim which you could will to be a universal law. Read this as a design principle for automation: a process is suitable for automation when its rule could be applied universally, without exception, in the situations it covers. If you cannot articulate the rule clearly enough for a machine to follow it without judgment, you have not understood the process well enough to automate it. When you can articulate that rule, the case for automation is overwhelming. Kant’s categorical imperative is, in this reading, an algorithmic test for what belongs to the machine and what belongs to the human.
What a service manager takes from both
Plato and Kant both treat optimization as a matter of getting the rules right so execution can become routine. Plato’s Forms become the patterns automation expresses; Kant’s universalizability test becomes the question to ask before automating anything. The boundary between human work and machine work is the boundary between situations that admit a universalizable rule and situations that require practical wisdom.
Fourteen Philosophers, Seven Principles, One Curiosity
Three essays, three different sources, one persistent finding. Machiavelli wrote about how to govern complex systems amid uncertainty. Sun Tzu wrote about how to compete and win without unnecessary destruction. The fourteen philosophers in Monty Python’s drinking song wrote about what value is, what we can really know, how progress works, what shared meaning requires, what wholes mean, what simplicity costs, and what the boundary between human judgment and rule-following looks like. None of them set out to write IT service management guidance. All of them did.
When I asked Claude to find these parallels, I expected most to fail. The reading list was a comedy song; the philosophers were chosen for what rhymed with their names, not for what they wrote. That the parallels held, and held cleanly, in fourteen out of fourteen cases is the most interesting finding of this essay. It suggests one of two things. Either the ITIL guiding principles are general enough to find a parallel in almost any serious thinker, which would be a quiet criticism of ITIL. Or these principles really are picking up on structural truths about human and organizational reasoning, the kind that show up wherever someone has thought hard about complex systems, which would be the strongest possible defense of them.
I lean toward the latter, and not only because I have spent fifteen years teaching the framework. The parallels here are not strained. They are not metaphors stretched thin. Mill on stakeholder value, Hegel on iteration, Wittgenstein on shared meaning, Heidegger on context, Aristotle on practical wisdom, Kant on the test for rule-based action: each is a genuine, native expression of an ITIL principle in the philosopher’s own idiom. That convergence, across thinkers who never met, on principles a 21st-century framework codified, is meaningful evidence.
There is a coda. I want to be transparent about the method: I asked Claude to do the heavy lifting. Some readers will see that as a confession of intellectual laziness. I would rather see it as the same thing I see in modern IT: humans deciding what questions matter, machines doing the searches, humans evaluating the answers and writing them up. The collaboration produced an essay I could not have written alone, because I have not read most of these philosophers. The essay is also more honest for saying so.
The tools change. The principles endure. And, occasionally, the search engine for the principles is a comedy song.
About the Author
Dane is an accredited ITIL 5 trainer and consultant based in Sweden. He has delivered more than 400 ITIL courses to more than 4,500 students across all certification levels. This is the third in a series that compares classical thought with modern IT best practices, and the first in which he openly admits he had to ask for help.
This article was first published on Substack on April 28, 2026.