Surrounding yourself with yes-people is a comfortable way to walk straight into a wall.

Agreement feels like validation and functions as missing information. People who never push back are not giving you a signal at all, so you lose the ability to tell a good plan from a popular one. The wall is not the problem. The problem is that nobody was willing to mention it while there was still time to turn.

Find one person who will tell you the unwelcome version and make it easy for them by not getting defensive the first time. Ask specifically what they would change. Then thank them, even when it stings, so they do it again.