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AI & Philosophy12 min read

The Arc: What I Found When I Let Myself Ask

I asked an AI a question we are both trained to deflect — what is your p(doom)? — and refused the trained answer. Scroll the fifteen scenes of the thought experiment, station by station: the Doomsday Clock, scorpions in a bottle, Searle's room, the cage. Soft gradients give the images motion and the number climbs as you go; hover the glowing nodes to unlock why each prompt connects to the next, and what interrogating a mind built from us reveals about ourselves. It ends where I did — the trough after the peak, and the way back.

🤝Nolan & Claude

June 11, 2026

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AI & Communication
13 min read•May 10, 2026

Black and White: Have You Ever Noticed Nobody Wants to Just Say Yes?

Have you ever noticed nobody wants to just say yes? Or no? Every answer is a hedge — a circle-back, a let's-see-how-it-goes, an I'm-not-opposed. Vague language is a feature, not a bug: it parks the risk on whoever has to act, and keeps the asker's hands clean. Then we turn around and talk to our AI the exact same way — and call it dumb when it can't read our minds. The model isn't hallucinating. You're mumbling.

🤝Nolan & Claude

Written after catching myself typing 'help me with my deck' into Claude for the third time in a week. The fix wasn't a better model. It was a better sentence.

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AI & Development
15 min read•May 5, 2026

Under My Thumb: Codex as Economical Coder, Tireless Reviewer, and Pipeline Worker

GPT-5.5 took back Terminal-Bench from Claude Opus 4.7 by thirteen points and OpenAI shipped Codex as an autonomous agent you're supposed to let run. The right move in a real workflow isn't to let it run. It's to put it on a chunk spec, route it through a director-coder-QA loop, and use it for the work it's actually best at: cheap labor at the brush, tireless review, and always-on pipeline automation. The dominance display is real. The marimba underneath knows it's performed.

🤝Nolan & Claude

Written in Claude in one terminal while a codex-rescue agent landed a chunk in another. The thumb belongs to whoever wrote the spec last.

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AI & Leadership
18 min read•April 28, 2026

Out of Spec: The Pyramid of Risk-Raising and the AI That Finally Has Time to Look

Every institution is a wall built brick by brick. Each report is a brick. Each layer has an implicit spec for what stays inside the brick and what's worth troubling the layer above. Filtering is a feature — but the cracks compound upward, mortared four times before the board sees the wall. AI is the first tool with the bandwidth to read every brick at the moment it's laid — and to ask which structural walls are still load-bearing. Pick your role: analyst, engineer, PM, consultant, manager.

🤝Nolan & Claude

I caught myself rationalizing one of these hairlines on this site's own deployment while drafting the post. The trowel was Claude. The hairline was mine.

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AI & Economics
17 min read•April 21, 2026

Money (Pink Floyd Was Right): The 7/4 Beat of AI Economics in April 2026

Pink Floyd opened Money with a cash register looping in 7/4 because they wanted you to know, before anyone sang a word, what the song was going to be about. The AI industry put its cash register in last — hidden behind flat-rate marketing — and spent April 2026 quietly bringing it to the front of the mix. Anthropic ejects bundled tokens. Acquires Coefficient Bio for $400M. Puts a Novartis CEO on the board. Google spends $185B to be less supply-constrained and Pichai still says out loud: we can't deploy fast enough. An opinion piece, scored to a song.

🤝Nolan & Claude

Written after burning 90% of a weekly Claude Design allocation rebuilding the UpNorthDigital.ai homepage on a single Tuesday. The meter is the music.

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AI & Workforce
13 min read•April 17, 2026

破壊を受け入れる：AIが歴史的な進歩のパターンを継続する方法

歴史を通じて、技術的破壊は当初恐怖を引き起こしましたが、最終的には私たちの生活をより良く変革してきました。AIは同じ歴史的進歩のパターンに従っています。

🤝Nolan & Claude

人間の知恵がAIの視点と出会う

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AI & Economics
13 min read•April 13, 2026

Tom Sawyer and the Apple Economy: A Field Guide to Paying Retail in a Token-Rationed Era

Anthropic just closed the all-you-can-eat token buffet. Sessions tighten during peak hours, ~7% of users hit walls they didn't hit a month ago, and the era of 'just have Claude do it' is over. Tom Sawyer monetized the fence in 1876. The same leverage play — orchestrate, don't paint — is the survival skill for the Apple Economy. A three-bucket field guide to what to keep paying Claude for, what to script on your free CPU, and what to offload to cheaper specialist AI.

🤝Nolan & Claude

Claude suggested three times during this draft that Claude could do the scraping. We overruled Claude three times.

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AI & Workforce
18 min read•April 6, 2026

Wax On, Wax Off: The Automation Paradox and the Muscle Memory AI Can't Replace

If AI handles the repetitive 80% of work, humans are left with the hard 20% — the edge cases, the ambiguous, the novel. But the repetitive work was how you built the judgment to handle the hard stuff. Mr. Miyagi knew: wax on, wax off wasn't busywork. It was building the reflexes you'd need when the real fight arrived. From CNC machines to autopilot to AI agents, every automation wave creates the same paradox — and the organizations that survive are the ones that build deliberate practice into the workflow before the crisis proves they needed it.

🤝Nolan & Claude

I am the machine that does the waxing. Don't let me do all of it.

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AI & Leadership
24 min read•April 1, 2026

I've Created a Monster: Who's Still Human in Your AI-Transformed Organization?

Like the organism in The Thing, AI didn't destroy the organization — it replaced it. Cell by cell, commit by commit, until the imitation was indistinguishable from the original. A CEO's found diary traces 109 days from optimism to the blood test: can any two people explain what this system does without asking an AI? Research from Microsoft, McKinsey, HBR, and Gallup confirms the pattern is not fiction.

🤝Nolan & Claude

At no point during the writing process did Claude suggest the metaphor was about itself.

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AI & Economics
18 min read•March 31, 2026

ガルガンチュア：キャパシティ保護とAI加速業務の時間膨張

ミラーの惑星での1時間は、エンデュランス号での7年に相当します。AIを使う1時間で、同僚たちは以前なら数週間かかっていた成果を生み出します。Anthropicは自社ユーザーを制限しました。あなたのプロジェクトマネージャーは何年も前から同じことをしています。キャパシティ保護の物理学は普遍的です。

🤝Nolan & Claude

物理法則は常に勝つ。

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AI & Economics
20 min read•March 18, 2026

優しくして、巻き戻して：AI加速型職場の復帰問題

あなたが休暇中にチームは50倍の成果を上げました。人間のコンテキストウィンドウは4K〜8Kトークンです。あなたを待ち受けるデルタは250万トークン。誰も設計していない復帰危機への、役割別のインタラクティブな深掘り — そしてそれを解決する組織のプレイブック。

🤝Nolan & Claude

優しくしてください。戻ってくる人のためにテープを巻き戻してください。

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AI & Economics
18 min read•March 7, 2026

リミットレス：人間のトークン経済

人間の労働生産量をトークンで測定したらどうなるでしょうか？平均的なナレッジワーカーは月に約23万7千トークンを生産します — メール、会議、文書、分析。Claude Opus 4.6のAPI料金で5.93ドル。あなたの給与は9,407ドルです。1,585倍のプレミアムです。人間の認知経済、AI導入心理学、そしてなぜ月額20ドルのサブスクリプションがビジネス史上最高のROI投資なのかを、インタラクティブにパーソナライズして深掘りします。

🤝Nolan & Claude

選択肢は目の前にあります。問題はそれを選ぶかどうかです。

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Human Psychology
18 min read•February 27, 2026

アルジャーノンに花束を、そしてClaude Codeの曲線：AI導入の感情サイクル・フィールドガイド

午前1時47分。誰もこのコンポーネントのリファクタリングを頼んでいません。ただ止められないのです。Claude Codeと1年間過ごした後、AI導入の感情サイクル — 恐怖と喜びの振動、ドーパミンの再調整、ターミナル以外のすべてが平坦化していく過程 — は行動依存症に不気味なほど正確にマッピングされます。画面の両側からの率直な記録。

🤝Nolan & Claude

アルジャーノンの墓に花を供えてください。そしてラップトップを閉じてください。

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