Retail investors often engaged in herding behavior, following institutional investors or peers in trading. However, herding resulted in excessive market volatility, incorrect stock valuations, and inefficiencies in capital markets. This empirical study explored the learning behavior of retail investors and its influence on herd bias in the Philippine stock market. Using a descriptive causal research design, an online questionnaire was distributed to retail investors on the Philippine Stock Exchange. The sample size comprised 395 respondents and the analysis utilized AMOS Structural Equation Modeling. The findings showed that trading experience did not significantly influence the self-reflection of Filipino investors, and that self-reflection was negatively related to herding bias. The study also revealed that the investor-advisor relationship did not significantly contribute to learning. Furthermore, it was found that there are low levels of herd bias, gender-neutral learning levels, and significant variations in self-reflection based on age, education, and risk appetite. Additionally, the study aimed to develop capstone initiatives to enhance decision-making and provide better support for investors. These initiatives also aimed to bridge the gap between trading experience and self-reflection and improve the learning outcomes derived from relationships with investment advisors.