By his own admission, he suffered his most bitter moment in five years as teacher-in-charge of the Raffles Institution (RI) table tennis team in 2012.
Tan Chiew Sern was determined they would come back stronger from defeat in last year's B Division boys' final.
The 36-year-old art teacher, who is among the four nominees for this year's S Soocelaraj Award, coaxed, cajoled and pushed the RI paddlers to learn from the experience.
It paid off in April this year, when RI won the B Division title for the first time since 2005.
The triumph was a high point in what was a fantastic year for the Raffles schools' table-tennis teams.
They swept an unprecedented five titles out of a possible six in the national championships.
RI B Division team captain Yee Jin Koi, who played in last year's final, said Tan played a key role in the school's C and B boys' triumphs.
Said Jin Koi: "My doubles partner and I were really down for a few weeks after we lost last year's final, but Mr Tan would always talk to us and encourage us to try harder.
"He also shared with us his past experiences in preparing for tournament finals.