Easing into Early

We are night people - always have been. And although we are functional in morning meetings, it's just not our prime time. We do understand that most of the world does not operate this way, and that we really should be working on this. So we thought getting a dog would help but Obie usually sleeps as late if not later than we do. Maybe this baby will help us out... but for the first 7 months - not so much. Casey was a night owl too it seemed from the beginning. We made the 12 midnight feeding the last of the "day" and let him sleep from there. That eventually became 11 pm and then more like 10:30 and then 10. No worries, he still sleeps well into the morning we thought. Then recently, a new fussiness and general crabby nature started to creep in about 8 pm. (I am talking about Casey of course) A few nights we even let him fall asleep then only to wake him up 45 minutes later to preserve his 10 pm bedtime. He was getting up about 9 am which was very doable (better than the 5 am alert and ready to play babies we have heard about). So one night we decided to let him fall asleep for the night at 8 pm and see what happened. We went to bed totally prepared for a 5 am wake up, but he slept until 7 am! We took this routine on vacation with us and it seems to be sticking for now. Here is the problem: No matter how exhausted we feel during the day and vow personally and communally that we will go to bed by 10 pm, something happens at the 8 am bedtime - WE ARE AWAKE. Our 15 + years of night owl living kicks in and we are ready to grab the to-do list and make some things happen! But if we stay up until 1 am, Casey is still up at 7 am ready to go, and who can blame him? He has been asleep (with a few short breaks) since 8 pm! Well, this has been going on for a few weeks now and we are pooped. We have a child who sleep 11 hours a night, there is no excuse for being this tired! This is the definition of stupidity!
Here is the other problem: Our calendar has not yet adjusted to the 8 pm bedtime - we find ourselves with night after night of being committed to being somewhere past 8 pm. Casey has always just come everywhere with us, so now what? He doesn't tend to fall asleep in public - he is far too social for such things. So do we take him along and wait for the meltdown to begin? Now that we know, the calendar will start to shift, but wish us luck in the meantime!
At least it has been a gradual adjustment - Casey will ease us into letting go of our night owl ways and busy evening calendar. And for that (and so many other things) we are very grateful!