As Rebecca pointed out in her beautiful reflection on the liturgical year, Advent, Christmas, and so many of our Holy Days of Obligation focus on Mary and the birth of Jesus. Not long after Christmas is the Feast of the Holy Family and the Feast of Mary the Mother of God, as if making it through Advent and Christmas weren't hard enough. Honestly, all the focus on Mary's pregnancy and maternity can make it hard for an IF gal to connect to her. (We're not pregnant, may never be pregnant, may never raise a child, much less be the perfect mother.)
While we can't and shouldn't remotely ignore Mary's role as the mother of Jesus, neither should we let a focus on her pregnancy and maternity interfere with our relationship with her. Mary is held up as the mother of the church, mother to all mankind, an example we should emulate. I think that there are two particular moments in Mary's life that we can focus on that can help us better relate to her.
1) Fiat - "Let it be done to me according to your will." - This is the obvious one, and the one that we struggle with regularly. In a very visible way we are called to surrender our desires, hopes, wishes, and plans for a family to God, and to accept His will for our lives. When well meaning others suggest contemplating this part of Mary's life, it can cause us to go ever so slightly ballistic (as they are sitting there with their seemingly perfect families, exactly how they planned them). That doesn't mean that it's not a valid point and not something to reflect on. It just means that it's hard.
2) The Pieta
Mary holding her Son's broken body, though perhaps not literally a moment in Mary's life, evokes the second point of connection. Mary was witness to the death of her child and mourned the loss of His life. Whether we literally mourn the loss of our children (through miscarriage) or do so more figuratively (in the loss of the children we had hoped and dreamed for), we can join Mary, knowing that even though her child was grown when He died, she suffered the same pain and agony of her child's loss. Did she feel guilt, knowing that her words at the wedding at Cana began Jesus' public ministry and the path towards his death? Our guilt is slightly different, but similar in that it can feel like our "fault" that our children do not live. Earlier, as the crowds clamored for Jesus' death, did Mary feel shame? Not understanding how God's plan is playing out in our lives, it is easy to be ashamed as others make assumptions about the reason for our lack of children, such as contraception, selfishness, sin, or a curse. Before the Resurrection, did Mary understand what God was doing through her and her Son? Probably not. We can join with Mary in confusion and pain and loss pictured in the representation of her as the Pieta.