Tim began his solo writing career in 1995. Shortly after he left the Doug Anthony Allstars, he commenced writing a series of columns for Western Australian street magazine, X-Press.

In 1996, he contributed an essay to acclaimed Australian author, John Marsden's book, This I Believe. On the heels of this success, he commenced working on his first novel, Left, Right and Centre, which was subsequently publish in 1997 to critical acclaim.

Tim continued his work with John Marsden in the following year, 1998, narrating two books, Looking For Trouble and Staying Alive in Year 5. The latter book eventually went on to win the 1999 TDK Australia Audio Book Award. Tim also began writing irregular articles for Melbourne newspaper The Age in 1998.

With the Australian Referendum on the Republic imminent, the Prime Minister released his preferred draft Preamble in March 1999. Tim followed this up with his own version of the Preamble, which proved somewhat more popular than the original!

In 2000, Tim continued writing irregularly for The Age, and also continued working on his second novel, Madhouse.