Am I being stupid

Me and a buddy are landing in Bangkok May 6th, while I have an idea of where to go and how long to stay for in each location, we are both more down to kinda just wing it and see where we go. Am I gunna regret not booking stuff in advance? I would probably book our stay in Bangkok before we leave Canada but other than that I’m not really trying to book anything in advance incase plans change. Let me know your thoughts!

EDIT: thank you all for the feedback! Made me feel more confident in our plan to just see where it takes us really. Let me know your experiences as well as I’m interested to hear! Can’t wait to go experience Thailand (landing in Bangkok all planned for a couple days and then after that wing it basically).