System & Flow

The Simple Newsletter - Issue # 065

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Adam’s Thoughts

What’s going right?

What’s going wrong?

What do I need help with?

These are the three core questions we ask at every one of our CEO mastermind dinners.

We’ve been doing this for over three years.

It creates an environment where 10 entrepreneurs, 10 “CEOs” can have real conversations. The kind where people open up about what’s actually happening. The wins. The struggles. The things they don’t usually say out loud.

And most importantly, it gives them a space to ask for help.

Because chances are, someone in that room has either gone through it… or is about to.

But this week, something different happened.

We didn’t follow the script.

Instead of jumping into the three questions, we started with origin stories.

One by one, people shared how they got here.

Some went back to childhood.

Some talked about major life milestones.

Some spoke about how much they hated their old jobs.

And what unfolded was a full picture of what built them… what shaped them… what gave them the drive to build what they have today.

It was refreshing.

And honestly, it was incredibly useful.

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Adam’s Lessons

Sometimes… you’ve got to go with the flow.

We all have systems. We all have ways we operate. And when things go off script, it can create a little anxiety (at least it does for me).

I’m very systematic. It’s why we’ve built the CEO Operating System.

But here’s what I’ve learned:

When you trust your system… you can step outside of it.

That’s where growth happens.

When you know your foundation is solid, it gives you the freedom to explore. To test. To try something different without losing control.

And that’s exactly what happened here.

By going off script, we found something that can actually improve the system.

That’s how you scale.

Not by abandoning structure... but by enhancing it through experience.

The danger is when people try to “go with the flow” without having a system in the first place.

Then it’s not exploration.

It’s chaos.

No controls. Just variables.

But when you have structure… and you allow for flexibility within it…

That’s where evolution happens.

And that’s exactly how we’ll be improving our mastermind dinners moving forward.

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So here’s my question for you this week:

Where in your business are you either too rigid to adapt… or too loose to improve and what would it look like to find the balance between system and flow?

Reply and tell me. While I can’t respond to every message, Tom and I read every reply, and we genuinely appreciate hearing from you.

That’s all for this week.

See you next Saturday.

P.S. Without a real system, “going with the flow” turns into chaos… but too much structure can keep you stuck. Click here to find out why so many business owners get caught between the two.