Eleven first-round defeats in 2004 saw his ranking plummet 100 places to 109 and things got so bad that the Australian almost hated the sight of a tennis court.
But a two-month break at the end of last year has given the former U.S. Open and Wimbledon runner-up renewed hope.
"I've been doing some good training and I'm feeling good mentally and physically," Philippoussis said as he prepared for the Hopman Cup in Perth.
Philippoussis will lead Australia's bid for the mixed team title with compatriot Alicia Molik, the women's world number 13.
"I just want to start the year off strong and just enjoy myself out there. It was hard to enjoy the tennis (last year) and I didn't. I just wanted the year to end," the 28-year-old said.
Philippoussis used the time off to practise with former world number one John McEnroe in New York.
"We did a bit of hitting, we did a lot of fitness as well with his (McEnroe's) physical trainer, and just a lot of talking, about what happened, what did go wrong and what I should be doing," he said.
"John is a busy man as everyone knows and he doesn't really need to do anything unless he wants to. He approached me which was incredible and I jumped at the opportunity."
Looking rested, Philippoussis was keen not to put any more pressure on himself.
"I know there is talk of people saying, if he doesn't do well here (in Perth), then it is over for him (but) I don't agree with that," he said.
"You can't expect someone to come back after training hard for two months and all of a sudden turn it on. If it does, bonus, great, but I am here to start off strong, fresh, positive and see how it goes."
Although he would love to do well at the Australian Open, where he has never been beyond the fourth round in nine attempts, Philippoussis said his main aim was to do well at Wimbledon.
"Of course, it (Wimbledon) is a dream, there is no doubt about that," said Philippoussis, who reached the final in 2003.
"It's something that when it comes along or gets close then I start getting excited and thinking about it."
Philippoussis and Molik begin their Hopman Cup campaign on Monday against Slovakia.