Background: Contemporary society is characterized by unprecedented levels of social surveillance and judgment, intensified by digital technologies that enable constant observation and evaluation. While philosophical traditions have long recognized the tensions between social conformity and authentic living, limited empirical research has examined how perpetual judgment specifically constrains autonomy and well-being in digitally connected populations. Objective: This study examined the impact of perpetual social judgment on individual authenticity and psychological well-being, investigating the mechanisms through which the social gaze operates and identifying conditions that enable authentic living in contemporary contexts. Methods: A mixed-methods convergent parallel design was employed with 847 participants aged 18-65 years recruited through stratified random sampling from urban and semi-urban settings. Data were collected using validated psychometric instruments measuring authenticity, social anxiety, psychological well-being, and social media intensity, alongside researcher-developed items assessing perceived social judgment and conformity behaviors. Quantitative analysis included univariate descriptive statistics, bivariate Pearson correlations, and binary logistic regression predicting high authenticity. Additionally, 32 semi-structured interviews provided qualitative insights into lived experiences of navigating social expectations. Results: Univariate analysis revealed that 51.4% of participants reported low authenticity, with moderately elevated social anxiety (M=34.67, SD=11.23) and moderate psychological well-being (M=64.82, SD=15.47). Social media intensity was notably high (M=4.83, SD=1.56), with 77.9% of participants engaging at moderate to high levels. Bivariate correlations demonstrated strong negative relationships between authenticity and social anxiety (r=-.612, p