OK, late night pop psyc it is then, reckon being positive and outgoing and winning are all very different things and mutually exclusive.
Winning at anything is about probability, e.g small businesses have a 50% failure rate, so start,fail,start again, repeat, the odds are going to be in you favour soon enough.
Positive – this is about realising you are responsible for how you feel or react not the outside world. Controlling your mind, steering your thoughts in to what will eventually be a habit,rather than just being the sum of your random experiences.
Outgoing – I believe this is down to genetics but I think you really mean either confidence (practice) or being happier – see positive.