Data scientists are in high demand, and sometimes the thrill of having skills that are actively sought after can cause one to make a career move without taking enough time to truly understand the expectations, skill requirements, or workplace culture of the new opportunity. In other instances, such as is sometimes the case in the academic job market, positions may be so difficult to obtain that one takes the first offer that comes along, without sufficient understanding of the department dynamics or teaching/university service expectations. In this talk, I will share reflections on questions I wish I had asked before jumping into a new job, and offer advice for those considering a new job opportunity, whether it is an opportunity to take on a new role within your current organization or a move to new position in a different organization or industry.