What does it mean for it to be well with our soul? How do we continue to push forward after experiencing hardship?
When we, as believers, are able to get to a point in our lives that no matter how hard or painful things might be, we can consider it to be "well with our soul" because we know we can trust God in the plans he has for our lives. We are understanding that this life is temporary, and we are working for our greater reward, eternity with Jesus. 
We all go through hard times and grieving is completely normal. But allowing yourself to let go of the hard things and allow God to take care of you, can get you closer to a place for you to believe that it truly is well.

Jeremiah 29:11
Job Ch. 7 and 8
Job 1:13-22
Acts 1:9-11
Acts 1:8