Between the Fall of 2016 through February of 2022 (the start of the pandemic) the author drove as an independent contractor for both Uber and Lyft--the ridesharing companies. During this time, he provided 4,590 rides (with a 4.97- star rating) in Boston, MA and the neighboring communities. When he decided to drive for these rideshare platforms, he did not intend on creating holding environments for developmental conversations. In this article, the author offers a selection of questions that can be infused into time-limited engagements with students that can create space for purposefully pausing and making meaning.