Ollie on Work

Ollie on Work

Home
Archive
About
Do you believe in 'hard work'?
Visible effort was always a proxy for value. AI removes it.
Jul 2 • Ollie Henderson
Your company was built for a problem AI just removed
What a 15th-century monk tells us about the shape of the modern company
Jun 25 • Ollie Henderson
Workslop and the skull that fooled Britain for 41 years
AI has made looking finished almost free. Someone downstream still has to find out it isn't.
Jun 18 • Ollie Henderson
AI has an Uber map problem
AI is being sold as a time multiplier. It isn't time we're short of.
Jun 11 • Ollie Henderson
Is your job a game the machine can already win?
AI takes the parts of work that look like a game. The rest is where the value is.
Jun 4 • Ollie Henderson
Who's flying the plane?
AI takes some skills off you and hands you others. The catch is choosing which ones to keep.
Jul 9 • Ollie Henderson
A booed billionaire and the deal that broke
Graduates are booing AI commencement speakers. It's not technophobia.
May 21 • Ollie Henderson
A Fitbit, a broken air conditioner, and the real test of your AI strategy
What AI makes cheaper may not be what matters
May 14 • Ollie Henderson
Ollie on Work
Ollie on Work
A weekly newsletter about AI, work, and what to actually do about both. Written by someone building with AI every day, not just writing about it.
Recommendations
Recruiting Brainfood
Recruiting Brainfood
Hung Lee
Category Pirates
Category Pirates
Category Pirates 🏴‍☠️
One Useful Thing
One Useful Thing
Ethan Mollick
Exponential View
Exponential View
Azeem Azhar
The Creativity of Work
The Creativity of Work
Allison Stadd 🥁

Ollie on Work

AboutArchiveRecommendationsSitemap
© 2026 Ollie Henderson · Privacy ∙ Terms ∙ Collection notice
Start your SubstackGet the app
Substack is the home for great culture