"I'm not saying I'm a poster boy for doing the right things," he says, "but I'm a poster boy for knowing what roads to take, knowing I have taken a few of the wrong ones."
Next weekend Sailor will be in Auckland for the inaugural nines tournament at Eden Park.
He will play with the likes of Andrew Johns, Gorden Tallis and Danny Buderus in an Australian media team that will take on a New Zealand side headed by Stacey Jones, Monty Betham, Richie Barnett and Wairangi Koopu in a game of touch nines before Sunday's final.
It's the latest in a long line of celebrity appearances. In 2011 he got into the ring with Liam Messam for Fight for Life ("I didn't really want to fight Liam Messam but sometimes you have to do these things otherwise you're a chicken," he says) and he's also been on Dancing with the Stars, Celebrity Apprentice Australia and in 2011 co-hosted Australia's Greatest Athlete.
The celebrity nines game will spark old rivalries but it is also for a good cause - appliances supplier Beko is giving $2000 to the Rising Foundation, a charity set up to help at-risk youth, for every try scored.
The charity is something that appeals to Sailor. He was bullied and racially abused at school and found out as a 12-year-old that he was adopted, something that affected him deeply.
But he cites sudden fame and fortune as his biggest pitfall. Today he preaches not being afraid to ask for help but it's not a message he heeded as a young player.
"I knew where to find help, but just didn't want to ask for it," he says. "I was never going through depression, but it was more that I had come from nothing and gone to the top and thought, 'how good is this?'
"At one stage I didn't want to play footy any more I just wanted to go out to the bars and be a rock star. But something had to give.
"I wouldn't change anything in my life. You make choices and the things I did hurt my career or myself more than anything else. You live and learn. If you want to be an elite athlete and be the best you can be, drinking and party drugs can bring your world crashing down.
"They were mistakes I wish I didn't make but you have to forgive yourself because if you don't how do you move on in life? People can be too hard on themselves when they make mistakes."