Recently, accrediting organizations have focused on developing lifelong learners who possess self-regulated and self-directed aptitudes of learning (hereinafter SELF-ReDiAL or in short, SR). This meta-analysis aimed to identify factors which promote or deter SR in health professionals. Original studies which, by using self-reports, evaluated enablers of and barriers to SR in health professionals (dentistry, medicine, nursing, and pharmacology), and were indexed in Scopus® and PubMed® databases from 1 January 2000 to 31 August 2022, were retrieved. Major themes suggested to affect SR were determined, and enablers or barriers related to those themes, were considered eligible for inclusion. Studies were excluded if they were not in English, and if the full text could not be retrieved. From 149 identified papers, 43 studies were subsequently included in the meta-analysis. The strongest effect was generated by wellbeing (d = 0.806; 95% confidence of interval [CI]: 0.296, 1.316). In respect of teaching method, problem-based learning (d = 0.590; 95%CI: 0.375, 0.806), team-based learning (d = 0.382; 95%CI: 0.232, 0.531), and flipped classroom (d = 0.095; 95%CI: -0.088, 0.279) showed positive effects on SR, whereas lectures were negatively associated with SR (d = -0.079; 95%CI: - 0.389, 0.230). Further, the analysis showed that SR generally decreases during the first year of enrolment (d = -0.144; 95%CI: - 0.284, -0.004), while no major change in SR is observed in the second year (d = 0.027; 95%CI: -0.044, 0.099). Considering that student wellbeing had the strongest observed effect on SR, policy-setting and governing bodies should incorporate methods which improve wellbeing to develop health professionals with high levels of SR. The online version contains supplementary material available at 10.1007/s40670-024-02068-y.