He grew up in Pasadena, California, having been introduced to the sport by an uncle who bought Sterling his first pair of skates at age two.

Playing with the Chicago Wolves, the Thrashers' American Hockey League affiliate, he amassed 55 goals and 97 points in 77 games.

However, he was unable to maintain a high level of play on the struggling Thrashers and was sent back to Chicago shortly into the season.

On June 23, 2010, Sterling was traded by the Thrashers, along with Mike Vernace and a 7th round selection in 2010 NHL Entry Draft (Lee Moffie), to the San Jose Sharks for future considerations in order to help the Thrashers facilitate an earlier trade of Dustin Byfuglien from the Chicago Blackhawks.

[8] After spending most of the year in the AHL Sterling was called up to the NHL on February 10, 2011, he made his Penguins debut later in the day in a game against the Los Angeles Kings.

[14] Sterling returned to Peoria and after playing 54 games and leading the team with 22 goals, he was traded (though his rights were retained by St. Louis) to the Portland Pirates for Patrick O'Sullivan.

[17] Sterling failed to establish his career offensive output totalling just 11 goals and 20 points in 43 games, before finishing the season on loan with SHL competitor Örebro HK.

On June 25, 2014, Sterling changed European leagues, in opting to join Austrian club, EC Red Bull Salzburg of the EBEL on a one-year contract.

As a free agent in the following summer, Sterling opted to return to familiar grounds, signing a one-year AHL deal with the Chicago Wolves on July 22, 2016.

[19] After continuing through to the 2017–18 season with the Wolves, Sterling registered 25 points in 45 games before opting to end his professional career after 12 years.