In the first three years of his education, he did not give any thought to what he would do in practice. Internships and work placements were uncommon at that time. Singh, however, was attending law school on a scholarship from DBS Bank, which came with a job and a bond. One of the requirements of the scholarship was that he spent three weeks a year at the bank, which he did. In his third year, he decided that he did not enjoy the prospect of being in-house counsel at a bank. That year, he attempted the Philip C. Jessup International Law Moot Court Competition in Washington, D.C. with three friends, Steven Chong, V K Rajah and Jimmy Yim. The team became the first from the National University of Singapore to win the prestigious moot, and Singh was named the Best Oralist in the Championship round. Singh decided that he enjoyed advocacy, and charted his career accordingly.