Parenting nightmares

My worst nightmare as a new parent is an overtired baby, ya hear? 

     We keep everything on a whiteboard (previously mentioned), when he eats, sleeps, poops, you get the point. Yet, Charles-Winston is more often than not extremely over tired by the time I get him to sleep. I've come to accept that squirming and flailing are a part of his sleep-time routine, the poor little guy will not stop until he's too tired to function, it may have something to do with his teething because it seems to have gotten even more difficult to get him to fall asleep this past week or so. 

     We're back to swaddling, if that tells you anything. He also gets frightened when he transitions from active sleep to deep sleep, so often times he'll wake up after napping for only about 20 minutes.

Clipping Charles-Winston's nails seems to be a recurring disaster. A few weeks ago, I was clipping his nails and accidentally took a chunk out of his thumb, he cried and cried and cried. It bled for two hours, then he finally fell asleep, when he woke up, he panicked and it bled for another two. This has happened twice now and I've only clipped his nails like 4 times in his life! (The rest of the time, Benjamin has bitten his nails). 

     It's so emotional for me to realize that my child is hurt because of something I did and I can't fix it. I've never felt as helpless as I did when I clipped his fingertip. I just really hope these feelings don't intensify as he gets older because as amazing as these parenting emotions can be, they're also quite debilitating when my child is injured.