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Work On Your Game: Business Strategy & Execution

Work On Your Game: Business Strategy & Execution

When Over-Optimization Makes Your Business Fragile [3787]

Work On Your Game: Business Strategy & Execution · Sep 26, 2026 · 23:32

0:0023:32

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A system built for maximum efficiency can struggle when conditions change. Optimizing one outcome can remove the flexibility you need elsewhere.

I break down the trade-offs behind optimization, why specialization can reduce adaptability, and why leaving margin matters. Examine where your schedule, systems, or decisions have become too rigid to handle the unexpected.

Show Notes:

[03:01] Point 1: Every optimization creates a trade-off.

[06:55] Whole Foods story: Customer service versus efficiency

[10:23] Point 2: Over Optimization Reduces Adaptability

[11:43] Design example: Why I rejected DIY artwork

[14:02] My move beyond basketball: Planning for a new business

[17:40] Point 3: Leave Margin for the Unexpected

[20:26] My recording standard: Podcast episodes versus audiobooks

[22:11] Recap

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Episodes: Work On Your Game: Business Strategy & Execution

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