As entrepreneurs gain expertise, the decisions that once felt easy become more complex and uncertain. This paradox suggests that while expertise is valuable, it also heightens awareness of potential pitfalls. Experienced founders reported feeling less confident despite their successes, illustrating how familiarity with complex variables amplifies doubt. The journey from novice to expert reveals that earlier confidence often stemmed from a lack of awareness about what one didn’t yet know. Ultimately, growing complexity is a natural part of evolving into a successful operator, marking expertise as a double-edged sword.
Every level of expertise you gain multiplies the variables you can see, increasing complexity and leading to greater uncertainty in decision-making.
One founder reflected, 'The more I learn about building companies, the less confident I am about every decision.' This captures the paradox of expertise.
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