On December 26, 2010, Oakley was hired as an assistant coach for the Charlotte Bobcats under then-head coach Paul Silas. He left that position on December 1, 2011 after experiencing health issues with back pain during the 2010-11 season.

Oakley turned his passion toward the kitchen. In 2008, he hosted his own unique cooking show, Cafe Oakley. His specialty: healthy options with savory and delicious flavors, notably; turkey burgers. He went on to open Red, The Steakhouse in Cleveland and another location in South Beach, Miami, FL. Oakley has displayed his culinary skills on several cooking competition shows, including Chopped Tournament of Stars on the Food Network, in 2014.

In 2013, Oakley and famed game developer Robert Alexander co-founded a free sweepstakes app, Kizzang® Sweepstakes, available on Web, Facebook, iTunes, and Google Play. The app offers free cash and other prizes through its daily slot tournaments, scratch cards, sports contests, and sweepstakes. The Oak in the Kitchen slot game and scratch card both feature Oakley as a chef building and serving burgers. Kizzang Sweepstakes garnered media attention in March 2013 with its $7.7 Million College Basketball Bracket Challenge™, and again in 2016 when Kizzang partnered with Sports Illustrated® to present the $25,000,000 College Basketball Bracket Challenge™.

Charles was inducted into the Virginia Sports Hall of Fame in honor of his 18-year professional basketball career. The induction ceremony was held on April 30, 2016.