Amidst a steady clamor about "learning loss" during the pandemic, a minority of educators have cautioned we must, in the words of Donna Haraway, "stay with the trouble," giving children space to grieve, explore, and make sense of a new reality. In this paper I interrogate what it means to stay with trouble and specifically call for what I refer to as "wander time" to stay with trouble in schools. With the phrase wander time, I reference the 40 years the Ancient Israelites spent wandering the desert after they left Egypt as slaves and before they founded a nation in Israel. Taking a phenomenological approach, I then illustrate the practical implications and the potential of wander time through a study of my then preschool-age son's yearlong self-directed and adult supported multimedia exploration of Transformers (vehicles in popular culture that transform into robots with human-like personalities). I document how through this exploration, my son articulated fears, stayed with, and made sense of troubles. I close by analyzing the pedagogy of wander time to suggest practical implications for schools.