The soul is very clear that its purpose is evolution...it is not concerned with the achievements of the body or the development of the mind. These are all meaningless to the soul. The soul is also very clear that there is no great tragedy involved in leaving the body. In many ways the tragedy is being in the body.
If all you desired is what your soul desired, everything would be very simple. If you listened to the part of you which is pure spirit, all of your decisions would be easy, and all the outcomes joyous.