Sidney began his career with the Boys Clubs of Greater Memphis as a part time staff leader at the Goodwill Boys Club. After graduating from college he began working as a school teacher and continued to work part time at the Boys Club until a full time position opened up.
He was hired as the Program Director and then as the Director of the Goodwill Boys Club. While at the Goodwill Boys Club Sidney’s team won four National Awards for Program Excellence. His merits led him to be chosen to open a new Boys & Girls Club facility in his South Memphis neighborhood.

In 1994 Sidney became the first Director of Operations for the Boys & Girls Clubs of Montgomery in Montgomery, Alabama. Two years later, he was recognized as the Southeast Regions’ Professional of the Year. Earlier in his career, Sidney was selected to participate in Leadership Memphis and continued participating in Leadership Montgomery as the Volunteer Chairman of the Youth Leadership Montgomery Program. The program brought high school juniors and seniors together to develop their leadership skills.

In 1999 Sidney accepted a position as Director of Training & Professional Development for Boys & Girls Clubs of America’s Southeast Region. While in this role, he provided leadership for The Practice of Boys & Girls Club Work, Master and Mentor’s Program and Advanced Leadership program for Youth Development and Management Professionals. Presently, his role has expanded to include BGCA’s Southwest Region.