For a long time I haven't been a good sleeper, and how I stopped caring was a real liberation for me, and a model for my further desire for spiritual freedom.
Back in college I used to sleep soundly for long periods. You wouldn't dream of getting up any earlier than to have just enough time to get a cup of coffee and get to your first class, no matter whether it was at 8:30, 10:05, or 11:30. On weekends, forget it. There was brunch until one in the afternoon, and I knew none of my buddies would be there before noon, so that's when I got up. Towards the end, when I had started to pray the Liturgy of the Hours a little bit, I would get up a little earlier to say Morning Prayer before the first class, unless the class was at 8:30. Do something before an 8:30 class? You must be kidding. I would go to the chapel after class and pray Morning Prayer at 9:30.
A couple of times I remember sleeping through a whole period of daylight, which I found very disorienting, so to speak.
But since those days I haven't slept well. I'm one of those people who goes to sleep but doesn't stay asleep. I wake up five minutes later, or half an hour later, or whenever. One of the best graces I have ever received is when I stopped caring about this or looking at it as a problem.
A few times in my adult life I have gone through a more intense sleepless spell; it's usually at a time that I later recognize to be much more spiritually important than I know at the time. The worst was during the fall right before I entered the Capuchin Order. I couldn't stay asleep, and my employment as a second shift worker didn't help much. When I did sleep for brief periods, I had very violent dreams in which I would sometime lose limbs. Once I had an eye gouged out.
Up until this time I was very annoyed at my sleeplessness. I would get all nervous and bitter about how I would feel tired the next day, think of all the things I would have to try to do with no energy, etc. I would try to force myself to go to sleep, which never worked.
And then, one day, I gave up. I knew I would be tired at work the next day, but I didn't care about how I felt anymore. Instead of tossing and turning and trying to force myself to sleep, I would save projects for when I couldn't sleep. At two in the morning I would be cleaning the apartment or out doing my grocery shopping. I was free, and whether or not I felt energetic or fatigued during the next day I tried to give thanks to God and work just as diligently.
Nowadays I try to take sleepless times as invitations to prayer. After all, God called the light out of the darkness, so perhaps its in the darkness that we might see the Light. And the greatest mysteries of our faith, the Nativity and the Resurrection, were both nocturnal events.