After re-signing with the Cubs as a minor league free agent in the off-season, Triple-A was clearly the next step.
Then, something happened. Sing started struggling. And struggling, and struggling, and struggling ...
He struggled so much that a .177 average and 33 strikeouts in as many games through the first month and a half at Iowa inevitably resulted in a demotion to the Southern League, where the pitching is almost always more dominant than in the Pacific Coast League.
Sure enough, Sing continued to struggle. But now he may finally be showing signs of coming around.
Sing picked up a season-high three hits in the Diamond Jaxx win at Huntsville on Sunday and unloaded off Chattanooga's Tyler Pelland in the third inning of the team's 8-6 loss on Wednesday night for a bases-clearing grand slam.
(Sing rounds third base following a third-inning grand slam against Chattanooga on Wednesday night at Pringles Park.)
All Sing himself knows is that he's finally seeing the ball with some consistency, and all it took were countless eye doctors, spread out city by city, to make it happen.
The problem first arose during Spring Training in Arizona when Sing, who wears contact lenses, contracted an allergic reaction that would affect his eyesight. It persisted throughout the first month of the season and lasted well after his initial demotion to Double-A.
"What happened was this [allergy] swelled my eyelids up to the point where my contacts were moving around and I couldn't focus on the ball," Sing explained. "When I'm in Arizona, my allergies always act up. The air was so dry there that my eyes started to get bothered and irritated. The irritation gradually got worse."
To rectify the problem, Sing eventually sought care from numerous eye specialists. He says he kept quiet about the initial vision problems because they would occur only periodically in the beginning.
"It had gotten better toward the end of Spring Training, then I went to Iowa and it started up again," he said. "I didn't say anything at first because every three or four days, it would be fine."
When Sing first decided to see an eye-care specialist near Des Moines, it wasn't long after that he was sent to West Tenn. Each doctor he saw offered different solutions and remedies, but it was an old friend who helped to turn his eyesight around.
"About a week and a half to two weeks ago, we had a day game and afterward, I went back to my eye doctor at home," Sing said. "I really trusted him, so I saw him and we took care of it.
"The lady I went to see in Jackson (Tenn.) told me that I was putting too many drops in my eyes. I got off one drop and got started on another. Then my doctor at home said I needed to keep taking the drop that I got off of, so all that kind of messed things up.
"Now, I'm on both drops, plus I've bumped up my contacts another notch."
With Sing now free of allergies, vision problems and anything else essential to his eyesight, he feels he's almost back to the point of a year ago, when he was batting close to .300 with 16 home runs already under his belt.
"It's been a roller coaster with my eyes," he said. "It's been one thing after another, but everything is getting better."
So is he really about to heat up?
"It's just a matter of getting my at-bats," Sing offered. "I'm seeing the ball again. Before, I was pretty much down to trying to pick pitches to swing at. That's why I was striking out. Now I'm seeing more pitches and am laying off pitches that I should. I'm starting to put the barrel on the ball and hit it solid again."