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This qualitative research explores how the broader social context supports employees' self‐directed learning (SDL) when using a personal development plan (PDP), focusing especially on the people manager's role. Based on deductive and inductive analysis of verbatim transcripts from 28 semi‐structured interviews with employees and people managers in a non‐profit organization, the study reaches three main findings. First, it confirms the key role that people managers play within PDP practices and their need to balance autonomy support, and structure, adapting their leadership style to employees. Second, it confirms the added value of PDPs for long‐term learning goals and for creating a “humanitarian corridor” for personal and professional development, where efficient formal learning is complemented by informal learning activities embedded and situated in the work itself. Finally, it articulates a new conceptualization of SDL within a broader social context. These findings are complemented by practical implications and directions for future research.