Pickens trained/trailed with numerous clubs in England and Scotland after his release, including Hibernian, Doncaster Rovers, Falkirk and Nottingham Forest, the latter of which he claims he was close to signing with.

[2] However, despite not securing a new contract in Europe, Chicago Fire traded Pickens rights to Colorado Rapids on January 15, 2009[3] and was signed by the club shortly after.

Early in the 2013 season, Pickens suffered a broken arm in a match against Real Salt Lake making this his last appearance with the Rapids.

Soon after signing with New England, Pickens was sold to Tampa Bay Rowdies in the North American Soccer League.

[5] On November 30, 2017 Nashville SC announced Pickens as the club's first signing ahead of their inaugural 2018 season in United Soccer League.

[7] In January 2020, Pickens was announced as the first goalkeeping coach for Major League Soccer's Nashville SC.