Society is a tricky thing. Society likes to praise things that can be questionable like paying singers and actresses more then some of our doctors and police men.
If I had to narrow being a "WINNER" in society I would say it would come down to how good of a job you make, how much money you make, how high of an education you have, how good you look, and how well liked you are.
But just because someone achieved all of this doesn't mean they are happy, that's why you should focus on things that could make you happy and feel like a winner. A quick example could be motherhood, some woman feel that being a mother is the most rewarding thing in the world, while others feel nauseous just thinking about changing a diaper. While it may be expected from society to have a family later in life that may not mean that will make you happy.
We have choices for a reason even if society doesn't agree with it.
A winner may not be a beauty queen or the last survivor in a reality show, although "The Amazing Race" does a good job of causing contestants to challenge themselves to achieve feats that bond relationships and help overcome problems in life after the show.
A winner knows what (s)he believes and maintains a solid belief set, but is willing to adjust beliefs in the light of facts to the contrary, while maintaining any faith that person has adopted. (S)he does not say "that was how I was raised" and not know why, and is not a blind follower of a pack of myth-perpetrators that is drowning in the deep end of the gene pool.
A winner is not the one with the most income and possessions, most Foodstamps, most Facebook Friends, most accolades for popularity contests, most children, or the most expensive food in his/her refrigerator, which is largely thrown out weekly.
A winner is one who can help take care of the Earth while pursuing goals that help the Self and Family (if any) and, hopefully, a few others.
A winner is not a person that jumps on the bandwagon of another who has a venomous agenda and a chip on his/her shoulder because of alcoholism, drug abuse, or any of a dozen explanations. This applies to some followers of some writers, politicians, highly-paid radio extremists and too many more to mention.
A winner is not the eight-year-old cohort dressing, makeup-ing, and gyrating akin to Miley Cyrus or Beyonce (who know how to use those elements to become millionaires at audience expense). Even though gyrating to a degree, Gaga and Katy Perry have heart, which Tony Bennett points out.
A winner is probably someone today that still understands the best work of Mark Twain, Will Rogers, Teddy Roosevelt, Robin Williams, Abraham Lincoln, MLK Jr., and Mother Theresa.
Other elements remain, but space is limited. Thank you for the question.
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