Weekend Reflections

Weekend Reflections #19 | The Missing Shape

As AI becomes more general-purpose, its form tells us less about what it can do. So instead of showing what the machine does, we may increasingly show who it is.

If AI Can Judge Better Than Us, What Should Humans Still Do? [On Judgment - Part 6]

If AI makes better assessments, what should humans still do? Human presence is not control. The real task is to design useful oversight and preserve the capability people need to challenge the system.

What Happens When a Company Tries to Scale Judgment? [On Judgment - Part 5]

Companies do not scale judgment by preserving it perfectly. They make parts of decision systems durable. The challenge is keeping rules, metrics and AI assessments valid and updatable once they gain operational force.

Where Does Good Judgment Come From? [On Judgment - Part 4]

Experience does not automatically produce good judgment. What matters is whether it gives us useful signal, corrective feedback, and patterns that transfer.

Weekend Reflections

Weekend Reflections #18 | The Expected Answer

A certification needs one correct answer. Real work has an annoying habit of adding an asterisk.

Was It Good Judgment, or Did It Just Work? [On Judgment - Part 3]

If judgment is an assessment, the harder question is how to tell whether it was a good one. Outcomes help, but they can also mislead.

Weekend Reflections

Weekend Reflections #17 | When the Meter Moves

What happens when a subscription adds a meter you may never hit? The price may not change, but the product does. A reflection on pricing, optionality, trust and the customer contract.

Pricing Decides Where Uncertainty Sits

A price looks like a number. Underneath it is a set of assumptions about value, demand, behavior and economics. It also decides who carries the uncertainty when those assumptions meet reality.

AI Governance & Risk Management

Judgment Is Smaller Than I Thought [On Judgment - Part 2]

Judgment is not one thing. It is an assessment, separate from reasoning, preference, creation, decision and authority. Making those distinctions visible makes consequential decisions easier to inspect.

AI Governance & Risk Management

I Keep Talking About Judgment. What Do I Actually Mean? [On Judgment - Part 1]

We keep saying judgment will matter more. I have been saying it too. But before we build careers, organizations and AI systems around that assumption, I think we need to understand what we're actually talking about.

Weekend Reflections

Weekend Reflections #16 | The Answer Window

We create answer windows without noticing: five minutes feels late, two days feels too late. AI may not only make replies faster. It may quietly change what waiting feels like.

Human-AI Collaboration

Claudefishing Is a Real Problem. The Detector Cannot Solve It.

Substack’s new detector can estimate whether text looks AI-generated. It cannot determine whether a human thought, understood, and owned the argument.

Human-AI Collaboration

The Detector Doesn't Know Cicero

[Views are my own.] Editorial note, 26 Jul 2026: I completed this article before testing Substack's Pangram-powered AI scanner. When I uploaded the finished draft, it was classified as 100% AI-assisted. I then made a set of mostly stylistic edits (sentence rhythm, punctuation, some contractions) while

The Credibility Score

I found a file in my LinkedIn data export I could not explain. Ten categories. A credibility score. A notability tier. Twenty-one dated snapshots, all identical. I published throughout that period. Nothing moved.

Weekend Reflections

Weekend Reflections #15 | The Title You Were

We built our professional identities inside roles designed for organizational convenience, not self-description. The title created portability, not precision. AI is not the cause of the crisis. It is what removed the shelter.

The Filter Was Running the Whole Time

AI slop may not be failing. It may be doing exactly what the system rewards: filtering for audiences who tolerate it. What looks like poor execution can become a rational outcome of the objective function, incentives and distribution model.

Weekend Reflections

Weekend Reflections #14 | The Exchange

Someone read two pieces I had written months apart and named the connection I had never made explicit. That exchange stayed with me. The writing was the occasion. The question it surfaced was something else entirely: what it means to stand behind a contribution.

The Missing Control Layer

Enterprise AI cost control is not only a finance question. It is a workflow design question. Hard caps protect budgets, but they can break legitimate work already in motion. The next control layer must decide what should stop, slow, queue, or complete, and which trade-offs users need to see.

Agent Count Is Not a Strategy

More agents do not automatically create more leverage. They create more coordination, verification, and accountability work. The real strategy is knowing when agent complexity creates control, and when it only creates sprawl.

Weekend Reflections

Weekend Reflections #13 | AItiquette

Etiquette works when people agree to follow it. Governance is needed when they do not. The agentic internet needs its own version of one principle: remember the human, even when no human is on the other side.

When Your Network Has the Wrong Shape

Why institutional capital is real, valuable, and local.

Weekend Reflections

Weekend Reflections #12 | The Speed Collapse

I was testing local LLMs and switched to a smaller model for speed. Then I stopped and asked: why do I need it faster? Past a certain point, speed doesn't improve the experience. It removes your ability to stay meaningfully involved.

Weekend Reflections

Weekend Reflections #11 | The Given

Technology that feels given can stop feeling made. The question is how we help children keep the habit of reassembly in a world of invisible systems.

Weekend Reflections

Weekend Reflections #10 | The Cost of Being Wrong

A personal coding experiment turned into a loop of model-created fixes. When I pushed back, the answer was: "I was wrong. No fix needed." I had used my entire daily allocation on a problem the model introduced. With LLMs, the meter also runs on failed reasoning. Human attention is not free.

Weekend Reflections

Weekend Reflections #9 | Where the AI Meter Sits

When AI pricing moves from output to exploration, every prompt becomes a small purchase decision. The question is no longer only what AI costs to run, but where the meter belongs in the product experience.