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The Architect’s Paradox: Uncertainty and the Philosophy of Software Architecture

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How do we make decisions as software architects? How do we create the conceptual structures that drive our architectures? Most architects cannot even begin to answer this question. The Architect’s Paradox is an investigation of the underlying philosophical beliefs of software architects. The book compares the journey of ideas in software to the journey in Western philosophy and reveals the default philosophy that most architects aren’t even aware they carry with them. It then asks what we can do that’s different, that moves architect forward beyond traditional thinking.


This book provides many chances to think about your own architectural practice, how you think, how you relate your software to the real world. It also serves as an introduction to philosophy for software architects who want a relatable way to get started, with every thinker and idea linked to challenges of building software systems.

171 pages, ebook

Published January 31, 2025

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About the author

Barry O'Reilly

2 books10 followers

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1 review
August 20, 2025
Grappling with the Architect’s Paradox

Have you ever wondered why we, as architects and software engineers, try to capture the world in a static way? One reason is, of course, that our work eventually has to run in a relatively fixed environment — servers, hardware, infrastructure. Our programs themselves are also static in the sense that they don’t change unless we change them.

The problem is the context around our nice, static, and mostly predictable world. That part isn’t static — it’s unpredictable, ever-changing, and constantly in flux. Or is it? Can we really predict the human context? Can we know exactly what users will want? We act as if we can capture it. We write requirements, define use cases, draw diagrams, and create architecture descriptions. But how should we actually define "the world" our systems live in?

That’s the question Barry O'Reilly explores in Architect’s Paradox. And honestly, it shouldn’t be surprising that we tend to think the world can be described in a static way — not if you’ve read even a little philosophy. Barry takes us on a journey from the ancient Greeks to modern times, showing how deeply rooted the idea is that the world is essentially stable and predictable. From Plato’s cave to Enlightenment rationalism, this thinking has shaped how we build things — including software.

But for years now, the software industry has had a gut feeling that this view doesn’t really hold up. Sure, the technical layer is mostly predictable. But the surrounding human and social context definitely isn’t. And that’s the architect’s paradox: we design for a stable system in the middle of an unstable world.
Barry’s books don’t just highlight the paradox — they also help us grapple with it. They offer a shift toward a socio-technical perspective grounded in a solid philosophical foundation. One of the key ideas he introduces is process philosophy — the view that everything is in motion, always evolving. Nothing is ever completely still or final. People, systems, and ideas are ongoing processes shaped by interaction and change over time.

This shift in thinking has real consequences. For one, it means we can’t just take our first design and call it done. We need to revisit, challenge, and explore our solutions from different angles — something Barry also dives into in his first book, Residuality Theory. But that’s a topic for another post.

I highly recommend both of Barry O'Reilly's books. They’re not always easy to wrap your head around, but I believe his ideas are a crucial part of how we, as an industry, can improve our thinking and our outcomes.
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