ISSUE #028 | THE LEADERSHIP CONTRARIAN

A quick note before we begin: at the end of last week's issue, I told you Uncertainty was next. It still is, one week from today. But today is the 250th birthday of the United States, and I couldn't let that pass without writing to you about it.

The Sword

There's an old sword leaning against a wall in our home.

A saber - long, thin, and tired-looking. It still has its sheath, tattered as it is, and the metal is pitted and tarnished.

It's the definition of old. Some would say it's a piece of junk.

I love it.

ISSUE #027 | THE LEADERSHIP CONTRARIAN

The first night, we had dinner at the Inn. It was spectacular. And because we were staying right there, we didn't have to drive anywhere, we just took a walk. Dusk was thinning. The stars were starting to come out. And then, in the air just over the dirt road, we saw lights.

ISSUE #026 | THE LEADERSHIP CONTRARIAN

Every serious business owner I've ever met says they care about culture.

Most of them have read the books. Listened to the speeches. Sat through the conference talks. They know it matters.

And yet, culture remains one of the biggest reasons people leave companies. One of the biggest drivers of inefficiency. One of the biggest sources of stress for the leaders carrying the weight.

So why does the problem persist?

ISSUE #025 | THE LEADERSHIP CONTRARIAN

Most leaders don't know they should get away to think and plan about their business.

Even fewer decide they should.

Even fewer still actually do it.

ISSUE #024 | THE LEADERSHIP CONTRARIAN

A leader I know said this on a call last week:

“My greatest tension is between my family and my business. My task list got so big I’m defaulting to sacrificing time with my family, skipping pickups, working from eight to eleven.”

Then, a beat later, something deeper came out:

“I’m thinking it’s up to me because God can’t help and I got to do all the work and I’m disconnected from how good He is and how much He can provide.”

Now, that second one is the real diagnosis. The first one is just the symptom.

ISSUE #023 | THE LEADERSHIP CONTRARIAN

I am, by most reasonable measures, weirdly obsessed with kitchen gadgets.

I own two sous vide machines, from different brands, and there's a story behind that. I have Cutco knives I bought back in college, and I still talk about them today - thirty years later - to anyone who will listen. I get genuinely excited about most cool kitchen gadgets. And I have strong, possibly unreasonable opinions about can openers.

Stay with me here. There's a point coming.

ISSUE #022 | THE LEADERSHIP CONTRARIAN

I want to tell you a story about the most confident I have ever been in my entire life.

It didn’t end well. For my ego, anyway.

It was the early 1990s. Kathryn and I had been married just over a year. We were living in Colorado Springs - beautiful weather, blue skies, the kind of afternoon that makes you feel like life had conspired in your favor.

I was on staff at a church, working as a youth pastor. And I was, if I’m being completely honest with you, absolutely killing it.

Or so I thought.

ISSUE #021 | THE LEADERSHIP CONTRARIAN

Why the expectation that sounds like a high standard is actually setting your organization up to fail.

A few weeks ago I was at my favorite Starbucks - the one between my house and the office, managed by a friend of mine I've known for the better part of twenty years. She introduced me to a new team member who had just transferred in. Already trained. Already experienced. She had worked at four or five other Starbucks locations and knew every part of the job.

I ran into that same barista again this week and asked how it was going.

ISSUE #020 | THE LEADERSHIP CONTRARIAN

The Post-Trust Era: Why the Leaders Who Already Value Trust Have to Go to the Next Level

One of my entrepreneurial friends, who has been running a successful company for over 30 years, said something to me recently that stopped me cold:

"It's just harder to make a buck these days," he said. "Our company's doing well, but you just have to work so much harder to make a dollar."

The look on his face told the rest of the story - a quiet exhaustion, and something just beneath it that felt like discouragement. He wasn't complaining. He was just being honest about something real.

I knew exactly what he was talking about.

ISSUE #019 | THE LEADERSHIP CONTRARIAN

Welcome back.

Do you ever feel like what people call random isn’t really random… and that history seems to repeat itself—but we don’t quite see the pattern while we’re in it?

There’s a pattern in history that shows up every 80 to 100 years, and it has a lot to say about what’s happening in our world right now.

And it’s not theoretical. It’s history, and it can help your leadership and your business right away.