Word From Between the Cans

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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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May 10 2026 Sarah Shepard

Go Find Something Bigger Than Your Problems

I took every photo I could at the top of Mont Blanc. Every single one came back looking like a nice mountain. That's a little like saying the Pacific Ocean looked like a lot of water. Accurate. Completely useless. So, I put the phone away and just ...

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May 1 2026 Sarah Shepard

The Label Is Never the Whole Truth

The Label Is Never the Whole Truth A few weeks ago in Giverny, I sat down to a Michelin-star dinner and said yes to the wine pairing before the sommelier finished asking. Not because I was feeling bold. Because I'd made a decision before the trip ...

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