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Toggle your inner critic
High taste is a superpower in review, but a liability during creation—separating judgment from making is the skill creators need most.
Tagged: leadership
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Will it work out?
Uncertainty has shaped human decision-making for millennia—from ancient dice to modern language models—teaching us to work with randomness, not against it.
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You didn't need to predict the App Store
Mobile blindsided many companies that moved slowly; AI will repeat this cycle—start small, measure, and upgrade every quarter.
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Willpower is not unlimited
Willpower and resilience are finite resources that must be managed strategically, not glorified into burnout.
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Projections on OpenAI after Altman
When risk-averse leadership replaces visionary founders, the focus shifts from innovation to asset protection.
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Stop romanticizing entrepreneurship
People aren't inspired by a hero's journey of suffering—they're inspired by movement and momentum. Entrepreneurship is just another path.
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Prioritize your questions like features
If you manage a work queue, you already know feature prioritization. Apply the same discipline to open questions.
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If your team is apologizing for doctor appointments
You have a cultural problem. Leaders who skip self-care send a signal that trickles down into burnout and risk aversion.
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I had a sleeping bag in my office
A decade of hustle culture experiments that made me no more successful—just less enjoyable to be around.
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On CEOs using company channels for politics
Thoughts on the Expensify email blast—I agree with the message but object to the channel. Apply the inverse test.
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On criticizing Mayer
There isn't a pundit criticizing Mayer that has ever managed a turnaround at a large company. Turnarounds take time.
- Quip
Executive punctuality is newsworthy