How difficult is it for you to ask.
Not everyone has difficulty asking but there are those for who "having to ask" is seriously disempowering. I count myself in this group so I know first hand the enormous COST this can be. It is to this person I suggest to take a little time and reflect back over your life and think of the times where to ask feels most uncomfortable.
To what EXTENT is overcoming the EXPERIENCE of having to ask as something that is so disempowering IMPORTANT?