In this paper, we explore the transferability of SSL by addressing two central questions: (i) what is the representation transferability of SSL, and (ii) how can we effectively model this transferability? Transferability is defined as the ability of a representation learned from one task to support the objective of another. Inspired by the meta-learning paradigm, we construct multiple SSL tasks within each training batch to support explicitly modeling transferability. Based on empirical evidence and causal analysis, we find that although introducing task-level information improves transferability, it is still hindered by task conflict. To address this issue, we propose a Task Conflict Calibration (TC$^2$) method to alleviate the impact of task conflict. Specifically, it first splits batches to create multiple SSL tasks, infusing task-level information. Next, it uses a factor extraction network to produce causal generative factors for all tasks and a weight extraction network to assign dedicated weights to each sample, employing data reconstruction, orthogonality, and sparsity to ensure effectiveness. Finally, TC$^2$ calibrates sample representations during SSL training and integrates into the pipeline via a two-stage bi-level optimization framework to boost the transferability of learned representations. Experimental results on multiple downstream tasks demonstrate that our method consistently improves the transferability of SSL models.