We decided that we should get Jase into a "big boy bed" before baby Maycee arrives, so he doesn't feel like his whole world is being taken from him when she gets here.
We bought this little bed at IKEA for a great price and let Jase help us put it together. He was THRILLED and jumped up and down on it and didn't want to leave. The first night was a breeze. He climbed right in and went to sleep on his own. Nap time was good the next day too. I was shocked how easy it was... but Jase is smart and deep down I knew he'd realize that this new bed brought on some new freedom as well. The next night he got out a couple of times at first- but once he realized that Ryan was right by his door to put him back, he gave up and went to bed. However, he did make another escape at 5 AM and crawled into bed with mom and dad. I didn't mind too much- it was super cute.
Overall the transition has been much easier than I thought. He does perfectly at nights now and has a few days here and there where nap time is more play than nap- but overall I'm impressed and happy that he's such a BIG BOY! Love that little guy!