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May 18, 2025 82 mins

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(Kaufmann Neworks are Boolean: see here if you want to know more, but you don't need to know anything about them to understand this episode)

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Embracing Uncertainty: Barry O'Reilly on Software Architecture and Philosophy

In this episode of Love and Philosophy, we sit down with Barry O'Reilly, a seasoned software architect with a deep background in pure mathematics and experience at top companies like Microsoft. He discusses his innovative concept, Residuality Theory, which introduces complexity theory into software development for the first time. Barry explains how traditional linear thinking in coding often leads to rigid and brittle constructs that fail to adapt to the constantly changing business environments. By embracing paradoxes and uncertainties using theories from philosophy and complexity sciences, Barry offers a new perspective on software architecture that combines the logical rigor of code with the adaptability required for real-world human systems. Join us for this thought-provoking conversation that bridges the gap between coding and philosophy, and learn how embracing uncertainty can lead to more resilient and flexible software solutions.

00:00 The Rigidity of Software vs. The Chaos of Business
00:46 The Philosophical Roots of Computer Science
01:28 The Architect's Paradox: Linear Thinking vs. Human Systems
02:20 Introducing Residue: Adapting to Change
03:16 The Relief of Embracing Uncertainty
04:16 Welcome to Love and Philosophy
11:34 Meet Barry O'Reilly: From Math to Software Architecture
16:02 The Journey to Complexity Theory
21:25 Handling Uncertainty in Software Projects
26:47 The Evolution of Software Engineering
31:42 The Birth of Residue and Ity Theory
38:17 The Need for a New Philosophical Approach
43:36 The Immaturity of Software Engineering
46:03 Personal Frustrations and Philosophical Pursuits
46:40 The Reflective Practitioner and Instinctive Problem Solving
47:13 Linear Thinking vs. Embracing Uncertainty
49:34 Philosophical Foundations in Software Engineering
01:05:03 Hyper Liminality and System Resilience
01:13:45 The Role of Play and Forgiveness in Software Development
01:19:16 Conclusion and Final Thoughts

Architect's Paradox: Uncertainty and the Philosophy of Software Architecture

Residues: Time, Change, and Uncertainty in Software Architecture.

You Tube Talks:

Residuality Theory

Architect's Paradox

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