The contemporary paradigm of trajectory learning operates fundamentally at the level of group dynamics, systematically reducing individual-level complexity to fit group-level models, thus rendering effective patient subtyping difficult and individual-level modeling largely out of reach. We propose a data-driven paradigm that introduces a dedicated individual-level temporal variable to capture \emph{Timing Attention} (i.e., the degree of concentration of an event's timing distribution across the patient cohort), thereby rendering timing a \emph{computable dimension} that enables individualized temporal features in trajectory learning. Instantiated as the Level-of-Individual Time Transformation (LITT) and applied to longitudinal EHR data from 3,276 breast cancer patients, the proposed paradigm demonstrates, for the first time to our knowledge: (1) automatic discovery of clinically significant patient trajectories, and (2) counterfactual timing deduction, that is, a \emph{What-If Machine}. Both results are purely data-driven, requiring no prior domain knowledge. LITT further achieves strong performance on timing prediction and survival analysis tasks.

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