Opportunity Cost Vs Trade Off

Is there a way to find out that you make the right choice?

Looking back, or creating a forecast can help - if you do x,y action and it comes to this reward - that means it was a good option right?

What about mitigating grief or bad choices?

This is something I struggle daily - and I've isolated it down to "Risk Management." which, is a term not so often used outside of financial analysis. But, it has been helping me lately in making the "best" choice,  but it always is not the "right" choice.

This is where I'm stuck at. What is the right choice. What would make me happy now, and tomorrow?

And how do I decide to cut off dead weight being relationships. Some of them really are not worth it.