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The Ride No One Warns You About

August 29, 2026 / by Michael Redman

posted in The Leadership Contrarian Newsletter

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ISSUE #036 | THE LEADERSHIP CONTRARIAN

They set a plate of carved meat down between the seven of us that somebody nicknamed the Beef Charcuterie Board. It was glorious.

We sat there for over two hours. Eating, laughing, going deep on what we were grateful for this year and what we'd learned the hard way. The conversation bounced everywhere, giving each other a hard time about nothing, then getting quiet enough to talk about the wins we were still excited about and the hard things we're still walking through.

I'll tell you why that dinner mattered so much in a minute. But first you need to know what the two days before it looked like.

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You Weren't Created to Lead Alone

August 22, 2026 / by Michael Redman

posted in The Leadership Contrarian Newsletter

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ISSUE #035 | THE LEADERSHIP CONTRARIAN

I can't remember his name.

I remember his face. I remember the way he stood at the front of that room like there was nowhere else he'd rather be. And I remember that he didn't care how many chairs he had.

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The Cat on the Ladder is Lying

August 15, 2026 / by Michael Redman

posted in The Leadership Contrarian Newsletter

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ISSUE #034 | THE LEADERSHIP CONTRARIAN

You've seen this interview.

Some founder who built something remarkable is sitting in a nice chair under good lighting, and the host asks the question they always ask: What taught you the most?

She pauses. Smiles a little. "Honestly? My biggest mistakes."

Everybody nods. It's humble. It sounds exactly like the truth. And a few million people walk away with the same conclusion: mistakes are the real teacher. Go make some.

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Who Encourages the Leader?

August 8, 2026 / by Michael Redman

posted in The Leadership Contrarian Newsletter

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ISSUE #033 | THE LEADERSHIP CONTRARIAN

I watched a room full of people spend an hour telling my friend Vicki what she meant to them.

 

It was her 60th birthday surprise party. About sixty people packed in, most of whom had known her for years, some for decades. Kathryn and I drove a few hours to be there.

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We're Not in a Storm?

August 1, 2026 / by Michael Redman

posted in The Leadership Contrarian Newsletter

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ISSUE #032 | THE LEADERSHIP CONTRARIAN

We're Not in a Storm. We're in a Stormy Season.

A few weeks ago I was sitting with one of my coaching clients. She started her company more than fifteen years ago, and in the last year and a half it has taken off. People from all over want what she offers. It's been exciting, exhausting, and everything in between.

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