ISSUE #012| THE LEADERSHIP CONTRARIAN

As I write this, I’m sitting in a small Airbnb in San Francisco.

Not because I’m on vacation.

I’m here because my sister has brain cancer.

Last week she began a six-week protocol of daily radiation treatments here in the city. It’s all still very new for our family, and we’re learning the rhythm of this journey one day at a time.

ISSUE #011| THE LEADERSHIP CONTRARIAN

I believe thriving should be normal in business.

But there’s a problem.

We’ve normalized “average”.

And in the process, we’ve watered down the very idea of thriving.

For decades, most of our systems - education, management, leadership development - have aimed at a simple goal: move people up to average.

If someone struggles, we help them reach the middle of the bell curve.

And if someone rises far above it, we treat them as the exception. Something unusual. Something rare.

"Good for you," we say. "You’re one of the special ones."

But average was never meant to be the goal.

ISSUE #010| THE LEADERSHIP CONTRARIAN

What Are You Actually Building Your Business For?

What’s the end goal?
And how will you know when you’ve reached the elusive finish line called “enough”?

Before we go any further, hear this:

I want the best for you. I want you to build a successful business and live a deeply satisfying life. I want you, when you’re old, to be able to say:

I lived well. I loved my family well. I built something meaningful. And the people who mattered most were still there at the end.

ISSUE #009 | THE LEADERSHIP CONTRARIAN

Hire Slow. Manage Less.

Most managing problems are hiring problems in disguise.

Not all of them.

But most of them.

When leaders tell me they’re exhausted from micromanaging…
When they say they don’t trust their team to follow through…
When they’re stuck dealing with the same performance issues over and over again…

I almost always ask the same question:

ISSUE #008 | THE LEADERSHIP CONTRARIAN

In the early days of Half a Bubble Out, we grew roughly 400% in about 18 months.

It was exciting.
and
It was exhausting.

Kathryn and I were buried in client work. We had a small team of six or seven people and the pressure was mounting. We knew we needed help managing operations and staff. We couldn’t keep doing everything ourselves.

ISSUE #007 | THE LEADERSHIP CONTRARIAN

Twelve days ago, it was a normal Monday.

I was having my monthly lunch with my sister, something we started about a year ago to be intentional with each other. We live four miles apart, but life fills up fast, and this was our way of slowing it down.

ISSUE #006 | THE LEADERSHIP CONTRARIAN

Leadership formation doesn’t stop at the office door.

A quick word before we get too far into this week’s topic.

Today, I want to be encouraging.

I want to offer you four practices - simple, powerful, and proven - that can add real strength to both your leadership and your life at home. They aren’t complicated. But they are formative. And when practiced consistently, they have a way of quietly changing everything.

ISSUE #005 | THE LEADERSHIP CONTRARIAN

This week I'm trying to communicate something from a different perspective...go with me for a moment while I back into my point.

The lights would dim. The heavy curtains would pull back. A touch of theater magic that doesn’t exist in the multiplexes of today.

ISSUE #004 | THE LEADERSHIP CONTRARIAN

As I’ve been writing these newsletters, a few of you have replied with a thoughtful question:

“Why The Leadership Contrarian?”

It’s a fair question.

Especially in a world already crowded with leadership voices, frameworks, podcasts, and hot takes.

So today, I want to answer it clearly - and honestly.

ISSUE #003 | THE LEADERSHIP CONTRARIAN

In the first issue of The Leadership Contrarian, I said this newsletter would be a journey, a conversation about leadership from a more holistic perspective.

Not just leadership as performance.
Not just leadership as personality.
And definitely not leadership as hustle dressed up as heroics.

But leadership as something deeper. More human. More sustainable.