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.

Unlike traditional software development, AI-native founders avoid long-term, deterministic roadmaps. They recognize that AI capabilities change so rapidly that the most effective strategy is to maximize what's possible *now* with fast iteration cycles, rather than planning for a speculative future.

In the current AI landscape, knowledge and assumptions become obsolete within months, not years. This rapid pace of evolution creates significant stress, as investors and founders must constantly re-educate themselves to make informed decisions. Relying on past knowledge is a quick path to failure.

The pace of change in AI means even senior leaders must adopt a learner's mindset. Humility is teachability, and teachability is survivability. Successful leaders are willing to learn from junior colleagues, take basic courses, and admit they don't know everything, which is crucial when there is no established blueprint.

Non-technical founders using AI tools must unlearn traditional project planning. The key is rapid iteration: building a first version you know you will discard. This mindset leverages the AI's speed, making it emotionally easier to pivot and refine ideas without the sunk cost fallacy of wasting developer time.

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.

While experience builds valuable pattern recognition, relying on old mental models in a rapidly changing environment can be a significant flaw. Wise leaders must balance their experience with the humility and curiosity to listen to younger team members who may have a more current and accurate understanding of the world.

In a rapidly evolving market, the speed at which you can discard outdated strategies and adopt new ones is more critical than simply accumulating new knowledge. Professionals who can let go of 'what has always worked' will adapt and win faster than those who cling to legacy methods.

To lead in the age of AI, it's not enough to use new tools; you must intentionally disrupt your own effective habits. Force yourself to build, write, and communicate in new ways to truly understand the paradigm shift, even when your old methods still work well.