I'm not sure whether I read or someone told me that it's never too late in the day to say the Rosary. Our Lady (and Our Father) will take whatever you have when you have it. Whether it's in the grocery line, while your waiting in traffic, or drifting off to sleep. They'll take what you got. Now of course, They'd love for you to do it with your complete devotion and attention on the Holy Mysteries (and you will get more out of it too) but they will take what you got. I was told that if you try to say the Rosary and you're sleepy, you can just pray, "angels, if I can not stay awake, please finish my Rosary for me." I'm not sure how kosher the theology of this is, but I like the idea that if my human weakness and sleepiness can't finish the job, I can call on some angelic help.
My ease of distraction either during Mass or during the Rosary is enough to get me discouraged. I don't know if it's because I'm a multi-tasked juggling a lot or maybe I have a little ADD, I just have a hard time focusing. Often during Mass, unless I'm wrangling my five year old (which happens frequently and is a semi-legitimate excuse for lack of attentiveness), it's the first time my mind starts to slow down, and so then many random thoughts come in- thinking about finances, my to-do list, all sorts of thoughts bouncing around. I will often ask Our Lady to help me focus on the reason I'm there and help take my distractions away. I'm sure I'm not the only one who suffers from getting distracted during prayer and Mass.
I believe the important thing though- whether you ask Our Lady or the angels to help that God knows if we are trying. We are human. He doesn't ask us to be perfect, he asks us to try and to trust in His grace. I often think the most difficult mystery for me to contemplate is actually "The Agony in the Garden". I think it really hits home for me. I think of the disciples trying to stay awake with Jesus in The Garden of Gethsemane and I think of how my fortitude is probably even less then them.
