Sad sad boy

Pumpkin and I have not had very much time apart in his two years.  Yes, he spends part of a day each week with a nanny while I work, he's been to lots and lots of playgroups, has been in coop preschool with me while I taught or assisted, and has been (rarely) with other coop moms while I taught or assisted.  He has not ever been dropped off with adults and children that he does not know for any length of time. 

Peanut, as you know by now, is going to an amazing school that matches her personality really well and has already drawn her out of her shell.  My thinking is that 1) I'm going to work to help pay for this, so I'd like to work at least some of the days she is at school.  2) It seems awfully silly to have the kids at two different schools or to have one home and the other in school.  3) He'll love it! 

So my plan is that he'll go two days and she will go four.  I'll work the two days they are both at school as well as the two other days I currently work.  We'll continue with our nanny, and I'll have time with the kids in the weekday afternoons as well as Sundays, and I'll have time with just Pumpkin on Monday and Tuesdays.  This all seems doable, except that he is super sad at school so far.  I know I know, it's only day two, but his little sad face in the pictures from today is just killing me!  He separated easily and I could leave without issue, but it looked like he was on the verge of a breakdown in all the pictures, and when I picked him up he was so very sad.  I mentioned that our nanny would be here tomorrow and he even said "mommy I need you here with me!" which is unheard of as he loves when the nanny comes. 

Now of course I am second guessing it all.  Alternatives are flying around my head.  Should I move all my Friday clients to Wednesday so I can be free to hang with the kids Fridays?  Should I just keep him home for longer and not worry about working more?  Should I just have him home and have a nanny two days while Peanut is at school?  Should I carry on and hope that he will feel more comfortable next week?  I feel like we should go on trying since it's so new, but still, my heart is in knots for the boy.  Oh my sad little man.  Sigh.