Dispatches from an Internet Pioneer

The Director of Central Computing

Managing the central IT organization is a real job. Governing technology across a research university is a different one.

Aug 11 • Timothy Chester

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Requestor Name Goes Here (Requestor Department Goes Here)

Why a requirement attached to a department instead of a person becomes an ERP risk no one can negotiate.

Aug 4 • Timothy Chester

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June 2026

Apple Just Settled One Question. Microsoft Opened the Other.

A week of announcements has clarified where everyday AI best lives. The institutional contest is just beginning.

Jun 15 • Timothy Chester

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May 2026

What the Work Has Been Arguing

A reader's guide to the ideas and arguments I keep returning to.

May 25 • Timothy Chester

Recap: The Canvas Breach Is Not a Tools Problem

Resilience to a SaaS event is built through leadership practice, not procured through another platform.

May 9 • Timothy Chester

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Certain About Everything, Agreed on Nothing

What three decades of technology did to our capacity for productive disagreement, and what skilled leaders can still do about it.

May 5 • Timothy Chester

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April 2026

In Defense of Overwhelmed Bureaucrats

How stasis and delay become the primary safe harbor for today's knowledge worker.

Apr 28 • Timothy Chester

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When the Code Works But the Decision Doesn't

Generative AI makes it easier to build software. It does not change the question of whether you should.

Apr 21 • Timothy Chester

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Isaacman's Inheritance: A SpaceX Mindset Meets a Legacy Institution

What the discipline of simplification reveals about leadership, culture, and change.

Apr 14 • Timothy Chester

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Two Kinds of AI Investment and Why the Difference Matters

A framework for building real AI capability without overcommitting before the cycle turns.

Apr 7 • Timothy Chester

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March 2026

What Service Disruptions Reveal: Negotiation Style and the Anatomy of Team Response

Why the same incident looks like failure, resilience, and a systems problem all at once.

Mar 31 • Timothy Chester

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The ERP Contract Doesn't Run the Project

What consulting agreements actually require from the people leading the project.

Mar 24 • Timothy Chester

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