Context and Chaos — Where context meets the chaos of building with AI
Where context meets the chaos of building with AI
Real takes from data and AI practitioners. No vendor slides. No hype. Just what actually happened, what worked, and why it matters.
Latest Issue
Your AI Dashboard Is Hiding Its Worst Failures
- A 92% success rate and a 61% success rate can describe the same AI system in the same week. Aggregate metrics compress millions of interactions into one number, and that compression is where failures hide: the dashboard describes the average experience while concealing the experiences that matter most.
- The most expensive failures live in segments nobody thought to define. Hidden stratification means a system can pass every declared breakdown yet consistently fail an intersectional cohort, like non-English queries about policy exceptions from first-time users, that no single-dimension slice will ever surface.
- The competitive question is shifting from whose model is better to whose team knows where its systems fail, and who they fail. That knowledge comes from treating subgroup evaluation as a first-class requirement: break every headline metric down by the dimensions that carry risk, then search for the underperforming cohorts nobody hypothesized in advance.
Practitioner Takes
Expert Directory
Austin Kronz
Data & AI Practitioner
Amanda Darcangelo
Sr. Lead Data Consultant, OneSix
Vivek Dubey
Data & AI Leader
Prukalpa Sankar
Co-founder, Atlan
Tathagata Das Sarma
Data Leader
Charlotte Ledoux
Data Governance Expert
Manoj Shanmugasundaram
Data Engineering Leader
Vince Dacany
CTO
Gaurav Ramesh
Director of Engineering
Jessica Talisman
Ontology Expert
Marc Dupuis
CTO & Cofounder
Mahdi Karabiben
Sr. Product Manager (Data & AI)
Sandipan Bhaumik
Tech Leader - Data & AI
Juha Korpela
Co-founder & Data Modeling Expert
Nandini Tyagi
Customer Experience Manager, Strategic Initiatives
Kurt Cagle
Ontology Expert & Knowledge Graph Architect
Austin Kronz
Data & AI Practitioner
Amanda Darcangelo
Sr. Lead Data Consultant, OneSix
Vivek Dubey
Data & AI Leader
Prukalpa Sankar
Co-founder, Atlan
Tathagata Das Sarma
Data Leader
Charlotte Ledoux
Data Governance Expert
Manoj Shanmugasundaram
Data Engineering Leader
Vince Dacany
CTO
Gaurav Ramesh
Director of Engineering
Jessica Talisman
Ontology Expert
Marc Dupuis
CTO & Cofounder
Mahdi Karabiben
Sr. Product Manager (Data & AI)
Sandipan Bhaumik
Tech Leader - Data & AI
Juha Korpela
Co-founder & Data Modeling Expert
Nandini Tyagi
Customer Experience Manager, Strategic Initiatives
Kurt Cagle
Ontology Expert & Knowledge Graph Architect
15+ practitioners. All perspectives.
Meet All ExpertsWhat is Context & Chaos Newsletter?
A free weekly newsletter for enterprise data & AI practitioners and leaders.
The field moved to context engineering. We moved with it.
Every week, practitioners who are actually working in the trenches — not the ones writing about them from the sidelines — share what broke, what worked, and what they'd do differently. We cover context graphs, data contracts, retrieval architecture, agent memory design, AI governance, and the full stack of infrastructure that makes enterprise AI reliable at scale. Context & Chaos is a community-led newsletter program distributed via Substack and LinkedIn to 20,000+ data and AI professionals worldwide. New issues land every week. All issues are free, permanently archived, and written for the people doing the work.
Who reads Context & Chaos Newsletter?
Built for enterprise data & AI leaders and practitioners. Context & Chaos is written for:
Context engineers
Designing the retrieval and grounding layers that AI agents depend on.
Data engineers
Building pipelines that need to be AI-ready, not just analytics-ready.
AI engineers
Deploying agents in production and hitting the limits of what foundation models provide out of the box.
Data governance professionals
Navigating AI compliance without blocking teams.
CIOs, Chief Data and Chief AI Officers
Making architectural bets on context infrastructure.
What each Context & Chaos issue covers?
Three types of issues. One commitment: no filler.
Practitioner Deep Dives
An external contributor who shipped something real writes about the actual architecture, the failure modes they encountered, and the tradeoffs they navigated. Contributors include engineers from fintech, healthcare, media, and enterprise data teams.
Editor's Take
Prukalpa Sankar, co-founder of Atlan, writes on what's shifting in the field — Gartner signals, community debates, vendor noise vs. actual direction.
Signal Pieces
Sharp recaps of events, research, and moments that moved the context engineering conversation. Short, sourced, opinionated.
No sponsored content. No vendor roundups. No AI-generated summaries dressed as insight.
Written by the community, for the community
Context & Chaos issues are written by practitioners and leaders across the field — data engineers, AI architects, governance leads, technical founders, and leaders sharing work from real-world production environments. We work with contributors to preserve their voice and protect specifics they cannot share publicly.
Frequently asked questions
FAQs on Context & Chaos
Context & Chaos is a free weekly newsletter on context engineering and enterprise data & AI infrastructure, with no paywall or registration required. All issues are published openly on Substack, LinkedIn, and the permanent atlan.com/context-and-chaos/ archive. Subscribers receive new issues every week by email.
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