A small and pacy rover, Pickett started his career in the 1990s with West Perth, playing three WAFL matches, but couldn't make an impact due to injuries.[3][4] In 2001 he tried again, joining Peel Thunder and the following season became the first ever player from the club to win a Sandover Medal.[2][5] He won his second Sandover Medal in 2004 while at Subiaco where he also enjoyed team success with four premierships.[2][6]
In 2008 Pickett was named in Subiaco's official 'Team of the Century' as a forward pocket.[4][7]
Pickett is married with four children. His oldest son, Alliston, also played for Subiaco,[4] and in July 2010 made WAFL history by being the first ever father and son to play in the same league game.[9] Pickett is related to Byron Pickett and Jeff Farmer. Pickett is credited with giving Farmer the nickname "Wizard".[10]