3 - I'd agree that it is not really a skill so much as an effect with many possible actionable causes, some of which can be trained. I think you and OP are actually coming at this from a similar angle if you indeed don't really care about winning. OP's point is that many people get sucked into doing things for reasons other than their impact on their long term happiness. Competitiveness, addiction, lack of experimentation can all lead to inefficient return on effort. There are likely many skills that can improve on these, but introspection towards your feelings/emotions to understand how your emotions respond to externalities is probably a cornerstone of many of them.