Wisdom vs Future Focus?

In my day job we keep repeating what seems like the same cycle – which is working with a collaborating company and then having that whole experience and everything we got out of it not meet our expectations. That has happened at least 4 times before.
The (what seems like a cycle) is starting again — a new collaborator has approached us and my boss is excited about all these new ideas with this new collaborator. My advice to her (doing something different) would be to not change our internal business development plans, and do this collab project as a side thing to test the water (vs what she wants to do which is blend all of our plans together)…. Here is my struggle: I want to be future-focused,and I want to be encouraging and supportive of my bosses creative vision but I keep raising a red flag with this new idea. Maybe I just need to change the way I think about it and not think about the past and let things unfold as they will?

Side note: Thank you for this program. It is hands down the best digital program I have ever been a part of. It’s changing my life. It’s inspired me to add coaching to my future plan so that I share this work with my world.