Word From Between the Cans

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July 7 2026 Sarah Shepard

What Happens When There's No Retention Budget

You're closing new logos, and the wins channel lights up every time, but your net number isn't moving the way the bookings say it should. The customers you fought to win last year are slipping out the back while you pay full price to replace them, ...

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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 27 2026 Sarah Shepard

Why High Performers Struggle to Be Present (And What One Hike Taught Me)

I almost missed Corsica entirely. Not the flight. Not the reservation. I almost missed the actual experience of being there.

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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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