When an artist looks back on his or her own career, there are always moments he or she can point to where there was a shift to another level. Those defining moments tend to be easy to spot with the benefit of hindsight but more difficult to see without the passage of time. Yet Chris Young has a sense that something is happening.

“I really do believe in timing,” says Young. “Everybody has a different point in their career when things start to come together and click, when it’s your time.”

Wi...