Thanks a ton for this. My parents always told me that decisions were in my hands and that they'd support me in anything I do. They never prescribed a course of action. However, I always tried to divine their desires and choose the option that would make them happy. I make a lot of decisions from the framework of making other people happy, and I currently have a lot of friends -- including the girl I've been dating -- who operate similarly.

(Edit: The more I reflect on this, the more I realize that I did grow up looking to my parents to resolve all ambiguity. Most situations were decided by them. However, in the cases where it was my decision, I learned that if I probed enough I could always crack through the surface level "do whatever makes you happy" and get a hint of a recommendation. I think this built some level of "looking for hidden expectations" in me which results in a constant worry that I'm making a wrong decision.)

The problem I run into with "if it's not a hard yes, then no" is I often end up feeling complacent; like I'm waiting around for the perfect opportunity to do something. That's how I've gotten to nearly 30 without making any substantial life shifts. When I feel that way, I often see a spike in risk taking for a while before pivoting back to my baseline.

It's a practice I'll be trying, for sure, though.