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.

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.

Lacking deep category knowledge fosters the naivety and ambition required for groundbreaking startups. This "beginner's mind" avoids preconceived limitations and allows for truly novel approaches, unlike the incrementalism that experience can sometimes breed. It is a gift, not a curse.

Instead of chasing trends or pivoting every few weeks, founders should focus on a singular mission that stems from their unique expertise and conviction. This approach builds durable, meaningful companies rather than simply chasing valuations.

Entrepreneurs often view early mistakes as regrettable detours to be avoided. The proper framing is to see them as necessary, unskippable steps in development. Every fumble, pivot, and moment of uncertainty is essential preparation for what's next, transforming regret into an appreciation for the journey itself.

Founders often start with strong intuition but lose it after achieving success. This occurs because long-held societal conditioning, which teaches individuals to distrust themselves and outsource authority to experts, resurfaces and mutes their inner voice.

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.

When transitioning leadership, you must allow your successors to make mistakes. True learning comes from fixing failures, not just replicating successes. As the founder, your instinct is to prevent errors, but you must permit 'fuck ups' for the next generation to truly develop their own capabilities and own the business.