when to ask and when to let it be...

Last night I was driving home and praying about something and a thought came to my mind that I want to share and get feedback on. I often am conflicted between praying that God bring something to me that I desire and just being accepting of His will. We know that we need to trust in the Lord and be uniform with his will but we also know that he said "whatever you ask will be given to you." In the Old Testament we have the story of Hanna who went to the temple every day crying and begging God to give her a child. Eventually he did grant her request. So how does one know when to beg with tears like Hanna and when to humbly accept the Lord's will and move on? Does anyone struggle with this? What are your thoughts?