Motherhood Mondays: Toby's first day of school

Toby started school this month, and on the first day, Alex and I took him together.
We went upstairs to his class, and he chose a car to play with. (Oh, that little belly.)
He slowly took it all in...
I sat for a few minutes to get him settled (and to check out how the awesome car doors opened!)...
He said hello to the other kids and introduced himself ("Tibby!").
Finally, after a few minutes, I hugged him goodbye. My heart was in my throat. Alex and I left quickly (like a Band-aid, right?) and Toby burst into tears. It was so tough! But we knew the teachers were great and that he'd settle down in a couple minutes and have a happy morning (and he did).
He had an awesome first week (he goes three mornings a week), and we were feeling great. But last week was harder. At night, I'd ask him if he wanted to go to school the next day and see his friends, and he'd shake his head, "No." And when Alex would take him in the morning, he'd start crying as they walked through the gate. The teachers told us, interestingly, that a lot of kids will seem fine the first week and then have a hard time adjusting the second and third week. We'll play it by ear—the school seems lovely, and has a pretty backyard with a playground and sweet teachers and art projects and a guy who comes to play guitar! Toby could, of course, wait a year to start school, but I think he'll adore it once he gets comfortable and really thrive in that fun social environment. To help him along, we have been talking excitedly about school and packing his favorite snacks (Cheerios, strawberries, bananas); and our beloved babysitter gave him a funny monkey backpack, which instantly became his best buddy (see above:). This week, he seems happier about everything, fingers crossed.

Did your kids ever have a tough time with school? Was the first day hard? When did your little ones start? I'd LOVE to hear any thoughts and advice. It's hard for both babies and parents! xoxo