Individuals earning over $150,000 annually may face significant financial losses due to complex tax rules and common mistakes. Issues such as Restricted Stock Units (RSUs), bonuses, and varying state tax regulations can unexpectedly increase tax bills. High earners often under-withhold or miss crucial tax planning opportunities, leading to avoidable losses. The primary challenge lies not in high income itself, but in navigating intricate tax laws that require strategic planning to prevent substantial financial setbacks.