Just as there are more disordered states than ordered ones for molecules, investing also involves unpredictable events, market movements, and potential pitfalls. The concept of entropy, which measures the disorder in a system, can be applied to investing. The statistical phenomenon of entropy emerging from the aggregate behavior of events explains why there are more random events moving towards disorder in finance. Without planning and intervention, investments are more likely to move towards underperformance. Continuous monitoring, analysis, and intervention are necessary to counteract the inherent uncertainty and volatility in investing. This article emphasizes the importance of keeping one’s eyes and ears open and taking the necessary action to avoid poor returns and missed opportunities.