This study examines the factors contributing to investment hesitation among Indian retail investors, with a focus on demographic variations in behavior. Using a mixed-methods approach that combines survey data analysis (N = 200) and a literature review, the research identifies key psychological, socio-economic, and structural barriers affecting investment participation. Findings reveal that only 5% of Indians invest in equities compared to 55% in developed markets, with significant hesitation stemming from fear of loss (reported by 65% of young investors aged 18-25), lack of financial literacy (only 27% literacy rate), and product complexity. The study highlights distinct patterns across age groups and genders, with women showing greater risk aversion and younger investors demonstrating higher susceptibility to behavioral biases like herd mentality. The paper proposes targeted interventions including simplified fintech interfaces, investor education programs, and regulatory reforms to address these barriers. By bridging the gap between traditional savings preferences and modern investment opportunities, this research contributes to financial inclusion efforts and offers practical solutions for policymakers and financial institutions seeking to expand retail investor participation in India's growing economy. The study's demographic-specific recommendations aim to transform hesitation into confident investment behavior across different segments of the Indian population.