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Why Every Entrepreneur Needs More Think Sessions

Eric Crews
|
10.23.2025
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Right now, many of my clients are in a prolonged problem-solving mode.

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They’re dealing with economic uncertainty.

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They’re grappling with questions around AI.

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They’re trying to build tangible plans in a moment when it feels like there’s very little to hold onto.

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Important activities? Yes. But they can wear you down. After a while, you start to only see the limitations, the challenges, the blockers to progress.

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That makes you less creative. It also makes running a business a lot less fun.

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If you’re feeling increased pressure right now, I’m going to suggest something counterintuitive.

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Don’t do more. Don’t grind harder.

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Stop and think.

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***

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We almost never get clarity from situations where there’s tons of pressure: time restrictions, immense stakes, deep emotions. 

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Instead, we get clarity from taking the pressure off. From stepping outside ourselves and getting a different perspective. From allowing space and time to do their magic and help guide us toward solutions.

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We need more Think Sessions. 

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You can conduct a Think Session on your own, with your leadership team, or with a small focus-specific group.

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You can hold it for an hour or a week. 

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Onsite or offsite.

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The point is to get out of operations mode and intentionally slow down your momentum.

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Less doing, more reflecting.

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Reflection usually generates the best ideas. And then, yes, you should go execute on those ideas. But you can’t jump from A to Z. 

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You need to go through the creative process first.

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Brainstorm ideas without evaluating them. Solve less. Ideate more.

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Remove limiting assumptions about what is and isn’t possible.

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The most valuable thing a leader can do is think—but you won’t think deeply or well if you’re stuck in the grind or constantly in firefighting mode.

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***

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Entrepreneurs should spend at least 25% of their time engaging in some kind of Think Session. Top performers spend close to 50% or more of their time this way.

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Think about those numbers and how well they align—or not—to your current calendar.

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It’s time to start making space.

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