The episode explores the multifaceted reasons why retirement plans often fail to meet expectations, despite careful preparation. It highlights the myth of predictability, emphasizing how economic volatility, inflation's hidden threat, and longevity risk can undermine financial security. The source also discusses the dangers of overreliance on single income streams, such as Social Security or pensions, and the common mistake of underestimating expenses like healthcare and lifestyle costs. Furthermore, it addresses how poor investment choices, like being too conservative or chasing high returns, and lifestyle and emotional missteps can derail retirement goals. Ultimately, the text underscores the importance of flexibility and continuous adaptation in retirement planning to navigate unforeseen challenges and achieve a fulfilling post-work life.