¡Hola!
"Plantear" in this context means something like "the way he/she thinks about his career, and even his/her life". It is related to the personal point of view the person in relation to his current and future situation, and the way the person is facing them.
In general, it means something like "consider" and "think about," but it can also mean "to present" and "lay out."
Espero haberte ayudado.