Some of the most successful CFers tend to also be "successful" at "life" using the typical measures (career, relationships, etc.)

Nepenthe- married, software consultant.
Zulghinlour- married, kids, lead test engineer
Valguarnera- no idea what his personal situation is, but he has a doctorate and is gainfully employed
Kastellyn- navy pilot, fairly high ranking, now doing administrative work
Twist- operations director at an ad agency
Balrahd- attorney, married, kid(s)
Graatch- no idea what his personal situation is, but he's an attorney so you know he's pulling down the bucks
Enbuergo- currently in law school, I think, so he'll be gainfully employed soon
The Pumpkin King- has a graduate degree and is doing tech work at a startup

Not sure what Jinroh, Karel, Jagaub and Marcus do, but I'm pretty sure Jagaub is well-compensated in some technical field.

I guess it depends on how you measure "winning".