Six years ago, Filipino Eugene Ranada had to dismount and push his bike up Sheares Bridge during OCBC Cycle's The Sportive Ride.
That "shameful moment" made the 45-year-old software developer, who weighed 115kg then, vow to conquer the steep slope one day.
Now 40kg lighter, the 1.73m Ranada had no problems as he pedalled his way up the bridge at yesterday's OCBC Cycle, completing the 40.8km route at the Singapore Sports Hub.
"It was challenging but also very rewarding," said Ranada, who took a selfie at the top of Sheares Bridge to commemorate the moment.
"I knew that it was steep so I had to pace myself. I was finally able to accomplish my goal and cycle all the way without stopping and that felt really good."
His weight started to pile on when he entered the workforce due to his sedentary lifestyle.
He weighed 120kg at his heaviest and was diagnosed with a heart condition that caused his heart rate to double without warning.
Motivated to turn his life around for his wife and eight-year-old son, he started cycling in 2015 and managed to shed 40kg between the end of 2014 to early 2016.
He is now an active member of local cycling group Joyriders and trains thrice a week.
Cycling with a friend yesterday, Ranada was impressed by the annual mass cycling event.
"It was well organised. I really appreciate the marshals, they did a great job keeping everyone safe.
"The route was good, it was slightly different (from 2012) and this time we can see more parts of Singapore."
While he enjoyed taking in the views of the Singapore Flyer, Marina Bay Sands and Gardens by the Bay, it was no surprise which landmark stood out for Ranada.
"I've been wanting to cycle up this (Sheares) bridge for years, all the hard work, the training, it finally paid off," he said.