Word From Between the Cans

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July 17 2026 Sarah Shepard

Spicy, Not Toxic: How Jay and I Argue Without Wrecking the Partnership

A few years back, Jay told me to stop shitting on his ideas. Not in an email, not in Slack, just straight to my face, after one too many meetings where he pitched something he was excited about and I started poking holes in it before he had even ...

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July 13 2026 Sarah Shepard

Why Experienced Teams Still Need Reset Days

I picked up Scott Galloway's The Algebra of Wealth expecting the usual bruising honesty he's known for, the kind of book that tells you things about money and ambition you'd rather not hear (or wish you had decades ago). And it delivered. What stuck ...

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July 7 2026 Sarah Shepard

The Hardest Part of Coaching Is Keeping My Mouth Shut

I was watching a teammate work through a client problem over Slack the other day. They were close. You could feel it in the way the messages came in, a little slower, a little more tentative, the answer basically forming in real time. And there I ...

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June 26 2026 Sarah Shepard

The StringCouncil: AI Advisors Who Won't Flinch

Nobody in their right mind invites Jocko Willink to sit in on a quarterly planning meeting. That's like asking a drill sergeant to supervise your morning workout. Sure, you'll come out stronger. You'll also hate every minute of it.

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May 18 2026 Sarah Shepard

The Exhaustion of Trying to Deserve Your Own Life

A few weeks into living in France, I stopped posting in our company Slack. Not because anything went wrong. Not because anyone said anything. I'd take a photo at a market or lift a glass of something good at dinner, and I'd feel this quiet shift. ...

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