At my recent Meet the Ringmasters gathering, we spent two days in a room with CEOs, founders, and operators comparing notes. Not just on strategy, but on what actually moves a business forward. It wasn’t a room lacking ideas or experience. If anything, there was an overabundance of both. What became clear, however, was that we were all carrying something else.

Clutter.

There’s a scene in Up in the Air where Ryan Bingham—played by George Clooney—stands in front of a room delivering a seminar. His job, somewhat ironically, is to fire people for a living. But in this moment, he’s not talking about termination. He’s talking about weight.

He asks a simple question: What’s in your backpack?

He then walks the audience through the idea that everything they’re carrying—commitments, obligations, unresolved decisions—adds weight.

Most of it, they don’t actually need to be carrying at all.

Sitting in that room in Sarasota, it became clear that executives do the same thing. Not with things. With decisions.

One executive described a promotion situation he had been thinking about for weeks. He knew the answer. He knew how to frame it. He even knew it would benefit the employee. He just hadn’t had the conversation.

Another described a team member who was productive, well-liked, and technically strong, but increasingly misaligned with where the business was going. Not a clear fire. Not a clear keep. Just… unresolved.

We saw it again in hiring. Several leaders admitted they had made decisions based on instinct—good energy, strong conversation, the sense that this feels right. Only later did they realize they hadn’t actually tested for the capability the role required. Confidence filled the gap where evidence should have been.

Why We Carry It

This isn’t a knowledge problem. It’s not a strategy problem. In most cases, the leaders in the room already knew what to do.

What they hadn’t done was act.

This is where Daniel Kahneman’s distinction between System 1 and System 2 thinking becomes useful—not as theory, but as explanation.

System 1 is fast, intuitive, and pattern based. It’s what allows experienced executives to move quickly, connect dots, and make decisions under pressure. It’s the muscle memory of leadership.

It’s also what makes us confident.

But it has a blind spot. System 1 doesn’t just help us decide quickly.

It helps us avoid discomfort just as quickly.

System 2 is different. It’s slower. More deliberate. It requires us to sit with a problem long enough to test it, challenge it, and, most importantly, act on it.

That’s where most of the decisions we carry live.

Because the issue isn’t ambiguity. It’s discomfort.

• The conversation you don’t want to have
• The role you know has changed
• The opportunity that looks real, but isn’t
• The decision that creates second-order consequences you’d rather not deal with yet

So, System 1 steps in with something that sounds reasonable:

• Give it more time
• Let’s see how it plays out
• Maybe it will resolve itself

And just like that, a decision that was clear becomes something you carry.

What Changed in the Room

No one needed help identifying their problem. But something shifted when those problems were spoken out loud.

Peers—people without internal politics or emotional attachment—offered something simple and powerful: permission.

The Cost of Waiting

Misalignment isn’t neutral. It slows teams down. It distorts hiring. It pulls attention away from what actually matters.

As a leader, you must make space to decide.

In most cases, it’s not capability. It’s lack of space.

For me, that space is formed in a simple end-of-week reflection log every Saturday morning: What went well? What needs attention? What did I learn?

This forces me to get what’s in my head onto paper.

What’s in your backpack?

Pick one decision you already know you need to make. Get it out of your head. Act on it.

Attendees at Meet the Ringmasters were challenged to add a calendar entry for June 13th to send me a note: Mission complete, indicating that the complex problem we discussed had been addressed and is no longer being carried around.

It may sound a little hokey, but it beats the strain on your neck of carrying too much in your “dome.”

What are you carrying that you already know how to put down?

You likely don’t need more time.

You just need to make a decision.