When your business no longer feels aligned, trust your instincts to make a change. The required pivot may be disruptive and risky, especially if the current model is commercially successful, but your internal wisdom is the most reliable guide for long-term fulfillment and integrity.

Success brings knowledge, but it also creates a bias against trying unconventional ideas. Early-stage entrepreneurs are "too dumb to know it was dumb," allowing them to take random shots with high upside. Experienced founders often filter these out, potentially missing breakthroughs, fun, and valuable memories.

The most significant founder mistakes often arise from abandoning one's own judgment to do what is conventionally expected. Jason Fried notes that these errors feel worse because you aren't just failing, you're failing while trying to be someone else, which undermines the core identity of your company.

Many professionals continue down paths they dislike simply because they excel and receive external validation. This pattern of ignoring personal dissatisfaction for the sake of praise is a form of self-betrayal that systematically trains you to ignore your own inner guidance.

The most common failure mode for a founder-CEO isn't a lack of competence, but a crisis of confidence. This leads to hesitation on critical decisions, especially firing an underperforming executive. The excuses for delaying are merely symptoms of this confidence gap.

From a young age, we suppress our authentic selves (intuition) to maintain connection with caregivers. This creates a lifelong pattern of seeking external validation over internal knowing, leading us to distrust our gut feelings.

Jason Fried advises founders facing inflection points to trust their own instincts rather than seeking external playbooks. An outsider can't replicate the founder's deep, irreplaceable knowledge of their business's history and decisions. The only path forward is to continue "making it up" based on that unique context.

Intuition is often overridden in professional settings because it's intangible. A bad decision backed by a rational explanation is often more acceptable than a good one based on a "gut feeling," which can feel professionally risky.

The number one reason founders fail is not a lack of competence but a crisis of confidence that leads to hesitation. They see what needs to be done but delay, bogged down by excuses. In a fast-moving environment, a smart decision made too late is no longer a smart decision.