In 1999, Mr Kwek Hiok Chuang, then a deputy director at the Ministry of Education (MOE), had to make a decision: stay on in his post, become a cluster superintendent or help set up a new junior college within just four months.
Finding teachers, coming up with a name for Pioneer Junior College and thinking about how to brand it in such a short period was daunting. But Mr Kwek, now 61, gamely opted for the task.
"I know it is challenging but I like to be with students, I think I can help them... that four months was fantastic," he recalled.
However, the experience was not without hiccups. On the first day of school, students piled into the lecture theatre at its holding site in Jurong East, but it turned out that the air-conditioning had broken down.
Mr Kwek, worried about the humidity, hastily drove to a nearby shopping mall, bought 15 standing fans and assembled them himself - just so that students could have a conducive environment to study in.
Two weeks ago, MOE announced Mr Kwek's retirement as principal of Nanyang Junior College (NYJC) at the end of the year, after 38 years in education during which he chalked up an impressive list of accolades.
He first made headlines at the age of 33, when he joined North View Secondary School and became Singapore's youngest principal then. At 38, he headed Anderson Secondary School in Ang Mo Kio and, within two years, it had leapfrogged 11 positions up the rankings table to claim 10th place in 1994.
At 51, he joined NYJC, nurturing the school's close-knit, caring culture to excel academically such that the cut-off point for the science stream was reduced from 11 to six points over the past decade.
After cutting red tape to encourage innovation, focusing on building a positive learning culture, and above all making students and staff feel cared for, it is no wonder that he has left a lasting impact on many of the almost 22,000 students he has met in the course of his career.
He said: "When students choose a school, they come to us with hope. What is important is that I rally my teachers and staff to make sure that they won't be disappointed.
"I know that when a person likes a place, they are prepared to do more."
The eldest of four children of a factory worker and a housewife, he grew up in a two-room flat in a tough neighbourhood in Bukit Ho Swee, where gambling and street fights were common. As a child, he loved tinkering with gadgets. After graduating from Nantah with a science degree, he became a maths and physics teacher at Gan Eng Seng Secondary School.
"I joined teaching because it was a stable job and we were poor. After living in that kind of environment where it was quite challenging, I feel that influencing the young is very important, to make sure that they behave positively."
Along the way, the Chinese-educated teacher overcame hurdles, building relationships with students in the school's worst class by understanding their problems, and improving his command of the language to teach classes in English. "If you teach with heart, the students can understand you. I had difficulty pronouncing some words, but the students were quite forgiving."
Social media posts attest to his humble spirit. Former students remember the down-to-earth principal who saw no act of service as being beneath him. Two years ago, a photo posted by an NYJC student, of Mr Kwek cleaning chairs and tables in the school's study area after a downpour, went viral.
Come Dec 31, Mr Kwek will hand over the baton to Mr Low Chun Meng, now principal of Manjusri Secondary.
"I believe we should not make ourselves irreplaceable, and should allow the continuation of the next leader. I spent the past 11 years making NYJC strong, and I'm sure the next principal will bring NYJC to greater heights."
Students, teachers and friends will bid him goodbye at a farewell assembly next month, but Mr Kwek's work is far from done. Already a volunteer with grassroots groups and the Chinese Development Assistance Council, he may join the business sector or become an education consultant.
"I want to keep myself busy, we should continue to work since we are healthy and still young," he said.