Calhoun, 70, told Sports Illustrated that he should expects to announce a decision on whether to continue his coaching career or pass the torch by mid-September.
"I would be very, very surprised if I didn't have something to say within the next two weeks," he said.
Calhoun said in July, while observing recruits in Las Vegas, that he could coach for several more years. He fractured his left hip in a bike accident in August, and the health challenges might lead Calhoun to more seriously reconsider retirement.
Calhoun was in a similar position last summer. He told reporters he would have a good read on his future by June 2011, but never made an official announcement.
"But I walked off the stage (with his championship team in April in Houston), there were 70,000 people and we had all those guys back. I couldn't do it," Calhoun told SI. "I thought we could do it again. We had the players. We had a team that won 53 games in two years. We've had 25 consecutive winning seasons. That's hard to do."
Connecticut has a new athletic director, Warde Manuel, said the university isn't committed to any "coach in waiting" or internal candidates if and when Calhoun steps away. His current contract expires in 2014.
The Huskies are banned from participation in the NCAA Tournament for low APR scores.
Calhoun has 873 career wins and three national championships in his career. He reportedly has pushed for former UConn guard and current assistant coach Kevin Ollie to replace him. Manuel said in May he wasn't planning to name a coach in waiting as Syracuse did with Mike Hopkins behind Jim Boeheim.