I dont think that has anything to do with empathy (I can certainly empathize with angry people at least lol). Moreso internal self-management. I think understanding mental models might help you. It's certainly helped me after revisiting a decade later and having more life experiences: https://www.amazon.com/Tempo-tactics-strategy-narrative-driven-decision-making/dp/0982703007
I'd highly recommend reading this this blog and ebook by Venkatesh Rao.
http://www.amazon.com/Tempo-tactics-strategy-narrative-driven-decision-making/dp/0982703007
http://www.ribbonfarm.com/about/
You ask when should you make a calculated gamble, and the answer is 'it depends.'