When one does not care about the outside world's perceptions and is successful. Especially if one fucks porn-stars.
Charlie Sheen is winning!
by Winningandloveit March 25, 2011
Get the Winningmug. To accomplish magical things that most people will never see in their boring normal lives, generally by: banging seven gram rocks (and finishing them), thus making Sinatra, Flynn, Jagger, Richards, all of them look like droopy-eyed armless children; having Tiger Blood; not dying; having one speed: go; and being proud of your drug usage, because it was RADICAL!
by Mr Reklov March 30, 2011
Get the Winningmug. An intrinsically motivated lifestyle in which there is no competition to "win" in the traditional sense since there is no "losing" to compare to. Winning is a way of life based on a determined dedication to doing only things that make you Win.
I'm quitting my job and partying all day.
-How will you pay for your house and car?
By Winning, that's how.
-How will you pay for your house and car?
By Winning, that's how.
by tyler fucking durden April 01, 2011
Get the Winningmug. Person A: Hey man, what did you do today?
Person B: Well, I woke up, forgot to feed my dog, found out I'm back on my credit card bills, failed two tests at school and then I got pulled over for having weed. But I got laid by two chicks!
Person A: Wow, how you feeling?
Person B: Duh! Winning!
Person B: Well, I woke up, forgot to feed my dog, found out I'm back on my credit card bills, failed two tests at school and then I got pulled over for having weed. But I got laid by two chicks!
Person A: Wow, how you feeling?
Person B: Duh! Winning!
by Winning2.5 March 26, 2011
Get the Winningmug. 
by hum27 March 17, 2011
Get the Winningmug. The state of constantly destroying every obstacle in front of you. To be a step ahead of and above everyone else.
by Matttttttttttttttfbfbdfb March 18, 2011
Get the Winningmug.