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Total Posts: 18
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Apr 16, 2024 First Post
Jul 2, 2025 Latest Post
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Unsent Letter #11

To the maestro who passed me byWhen I first met you, I tried to stand taller. Look bigger.You were quiet as a breeze, your manner good-natured, your visage a buddha...

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1 week ago

When AI Has Better Taste Than You

How machines conquered our skills, infiltrated our aesthetics, and left us with one final advantageWittgenstein once wrote that when the eye sees something beautiful, the hand wants to draw it.This...

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2 weeks ago

Unsent letter #47

To the corporate jobber with a faraway gazeThis is a paid subscribers post. I’m experimenting with sharing more personal writing with this smaller group, like little diary entries that feel...

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1 month ago

The Thing You Are Expert at Will Be Your Career Downfall

AI will disrupt some of us more than others.i.Last year, I wrote 189,214 words.Not because a boss demanded it, or a paycheck dangled at the finish line. I wrote these...

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1 month ago

Conversational Interfaces: the Good, the Ugly & the Billion-Dollar Opportunity

The five biggest problems with today’s conversational chatbot designi.ChatGPT launched from OpenAI on November 30, 2022, and in two short months, broke consumer app records like a bull in a...

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1 month ago

The AI Quality Coup

What exactly is “great” work now?What is quality work nowadays, in the era of AI? Traditional definitions are being upended, and it’s up to us to find the new precipice.This...

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2 months ago

The Death of Product Development as We Know it

Goodbye three-legged stool, 2-pizza teams, and “managers”Much has been written about what AI’s magical powers can enable — whether engineering, design or documentation. But I believe something just as interesting...

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3 months ago

Our Souls Need Proof of Work

On wanting and comfort in the era of AIDear Readers: I’m starting a series exploring AI and how it might change us — the way we work and learn and...

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4 months ago

The Valuable Employee Paradox

The good, bad and ugly of hierachyThe Valuable Employee ParadoxHere’s a seeming paradox:Every great manager I know tells me that the reports they find most valuable are the ones who...

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5 months ago

The Looking Glass: What Aladdin Should have Wished For

A letter to my daughter about happinessDear Readers,Where has the time gone? The sun casts its daily spells and now the twilight of another year upon us.I’ve spilled much digital...

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6 months ago

The Looking Glass: All the world is made of trust

That, and faith, and pixie dust.Dear readers,I used to think the glittering prize of a hard-fought battle, of a well-played game, was winning.But winning what, exactly?Was it the glory, the...

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9 months ago

The Looking Glass: Sharpening Judgement

The art of making better decisionsDear readers,What do you feel when you hear the word judgement?Is it a hit of cortisol — Oh shit, I hope you’re not judging me.Is...

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9 months ago

The Looking Glass: The Curse of Perfect

In the house that I grew up in, there was a formula for the American Dream.Dear Readers, I’m working on 2 new pieces that are in varying states of draftiness....

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10 months ago

The Looking Glass: Managing your Manager

Stop tolerating mediocre managementDear Readers,Some of us will be formal managers. Many more of us will have formal managers.Unfortunately most of us do a shitty job of getting the most...

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11 months ago

The Looking Glass: Culture Changers

More like a forest, less like a Stonehenge. A deep dive into what culture really is, and how you can go about evolving it.Dear Readers,Which of these entices you more?A...

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11 months ago

The gifts of 40

Unintuitive life lessons I wish I’d learned earlierDear Readers,I have consumed a thousand remixes of Thing I’d wish I’d known when I was younger. I gobble them up — every...

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1 year ago

The Looking Glass: Holding Up the Mirror

The what, why, how and art of giving and receiving feedbackDear Readers,I just went through feedback season at Sundial, and just like Christmas it’s full of gifts.This is a total...

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1 year ago

The Looking Glass: The Origins of Leadership and Burnout

The hero’s journey, and where things go wrongDear readers,I meant to sit down and write what I’ve learned about innovation, but somehow in the process this morphed into a different...

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1 year ago