THE SUBSTACK

Unexpected Insights

Essays on strategy, attention, and the odd places belonging actually comes from — plus a running log of what I do with AI every week. Published on Substack since 2021.

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PUBLICATIONS & GUEST ESSAYS

Guest essay · ZINE

Self-Sabotaging Innovation: The Art of Doing Dumb Shit

Breaking free of passivity, apathy, and corporate FOMO

Co-authored with Matt Klein for ZINE, his cultural-intelligence Substack with 1M+ readers in 150+ countries — and this is its most-read essay of all time.

Read on ZINE →

The Truth About Professional Women & Eating Disorders

A deck I started publishing for NEDA week. Updated August 2026.

Read on Google Slides →

Black and white photo of a desk with scattered papers, folders, and a person's hand, next to a manual titled 'Simple Sabotage FIELD MANUAL' with additional text 'Strategic Services' and 'Strategic Services Field Manual No. 3'.

How to Speak Strategist: What is it you say you do here?

The greatest irony about being a strategist is how difficult it is to explain what you do. This is my best take.

Read on Google Slides →

Strands of Genius: Featuring Elisabeth Bromberg

Long-form interview in Faris & Rosie Yakob’s newsletter (15k+ subs).

Read on Strands of Genius →

Start here

Seven essays that hold up

A notebook with a detailed, handwritten mind map or diagram filled with notes and interconnected ideas. A black pen rests on the notebook on a wooden surface.

May 2026

The ADHD Brain on AI

What 5,000 conversations taught me about the power of AI for neurodivergent brains (and the half the conversation is missing)

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Split image of two men, one smiling and the other with a serious expression. The man on the left has light skin, brown hair, glasses, and a light-colored shirt, while the man on the right has a darker hat, glasses, a mustache, and beard, and wears a dark suit.

Apr 2025

Truth in Tension: Why Complexity Matters in an Age of Absolutism

Nuance isn’t softness—it’s resistance.

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Laptop computer with a bright screen on a wooden desk, a mug, and a notebook with a pen in a dimly lit room.

Mar 2026

Full Screen

On fragmentation, the translation tax, and what it costs when your mind belongs to everyone but you

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Close-up of pink tulips with water droplets, with more tulips in the blurred background.

May 2026

Stop Apologizing for Your Em-Dashes

The cultural backlash against AI-coded writing has politics, and the politics has receipts.

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A panel discussion with four speakers seated in front of an audience, with large screens displaying the topic 'Are We Thinking About Attention All Wrong?' and the logos 'Cannes Lions' and 'Different Minds' in a decorated room with purple lighting and hanging pendant lights.

Jul 2026

Into a Microphone

On the math of saying it out loud

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A person's hand gently touching the surface of a dark liquid, creating ripples.

May 2025

Between Dopamine and Discernment: Navigating AI’s Sacred Pretense

Finding truth in an age of algorithmic wisdom

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Three headshots of diverse adults with short red and brown hair, wearing professional attire, against different gray, colorful, and plain backgrounds.

Apr 2025

How ChatGPT “sees” you: A three-part experiment

The problematic assumptions AI makes about us, and what it tells us about culture

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