It’s always been hard for him to have a good routine. Sometimes he goes to sleep late watching videos, other times he wakes up a thousand times during the night asking for water or looking for his stuffed animal. Today I tried to put him to bed early, but he tossed and turned, complained that he wasn’t sleepy, and ended up falling asleep much later than I wanted. I know that if he doesn’t rest well, he’ll be irritable tomorrow, maybe cry more, or have a hard time separating from me. I don’t want his first day to be a nightmare because of a bad night. What can I do to help him sleep better?
Omg, I feel this so much. My son just started daycare a few months ago, and the first week was rough because his sleep was all over the place. The first day, he barely napped, cried at drop, off, and was just out of sorts all evening. But honestly? It got better way faster than I expected. I was worried he’d never adjust, but after a few days of being so tired from all the new experiences, he actually started sleeping better at night. The first day might not be perfect, but I promise he’ll adapt! 
I don’t get why sleep is such a struggle for toddlers. Like, they’re exhausted but still fight it?! My kid does the same thing, tossing and turning, suddenly needing a drink, or remembering some random toy he absolutely must find at 10 PM. I’m curious, does your son still nap? I feel like my kid naps too long some days and then bedtime is a disaster, but if I cut the nap, he’s a wreck by 5 PM. It’s like there’s no winning lol
Okay, I’ve been there, and what finally worked for us was a super consistent routine and a little tough love. First, we cut out screens at least an hour before bed, game changer. Then, we made a short, predictable routine: bath, PJs, one book, and lights out. I also started telling my son, You don’t have to sleep, but you do have to rest, which somehow made him less resistant. The first few nights were rough, but after a week, he was falling asleep way easier. It’s so hard at first, but if you stick to it, it really does help!
I know it feels like everything hinges on this one night of sleep, but I promise tomorrow won’t be as bad as you’re imagining. He might be a little grumpy or clingy, but daycare teachers have seen it all, and they’ll know how to handle it. Plus, the excitement of the new environment might carry him through. Worst case? He has a tough morning, but he’ll still make it through the day, and you’ll both get another chance to try again tomorrow. You’re doing an amazing job preparing him for this big step, hang in there! 