Planning your career is a bit like planning a relationship: hard to do and not always advisable. When looking back over a career, most people describe an organic process of personal growth and openness to opportunity. The world of work is constantly evolving, making it difficult to predict how your career will change over time. Additionally, your needs and interests will change.
Because there is so much that is unknown, it is difficult to make a long term plan. Short term planning however, is easier. Below is a timeline for postdocs that will help you plan your career while at Yale: