When Yip Man was thirteen years old he started learning Wing Chun. Because of his sifu's old age, Yip Man learned most of his lessons from his second sihing Ng Chung-sok. After three years Chan Wah-shun died, but one of his dying wishes was to ask Ng to continue with Yip's training.
At age sixteen, Yip Man went to attend school at St. Stephen's College in Hong Kong, which was an upmarket secondary school for wealthy families and foreigners who lived in Hong Kong.
According to one story, one day one of his classmates challenged him to try his martial arts skill with an older man. The man who Yip Man competed against beat him with a few strikes. It turned out that the old man was his sibak Leung Bik (梁璧), son of his sigung. After that encounter, Yip Man continued to learn from Leung Bik. At age 24, Yip Man returned to Foshan, and his Wing Chun skills had improved tremendously while he had been away. His fellow students believed he learned a different kind of martial art and treated him as a traitor to Wing Chun.
In Foshan, Yip Man didn't formally run a Wing Chun school, but taught Wing Chun to several children of his friends and relatives. Amongst those informal students, Chow Kwong-yue (周光裕 (六仔)), Kwok Fu (郭富), Lun Kai (倫佳), Chan Chi-sun (陳志新) and Lui Ying (呂應) were the most well known. Chow Kwong-yue was said to be the best student among his group of pupils, but he eventually went into commerce and dropped out of martial art all together. Kwok Fu and Lun Kai went on to teach students of their own and the Wing Chun in the Foshan and Guangdong area was mainly descended from those individuals. Chan Chi-sun died young, and Lui Ying went to Hong Kong; neither of them taking on any students.
During the Japanese occupation of China, Yip Man refused several invitations to train the Japanese troops. Instead, he returned to Hong Kong and opened a martial arts school. When he initially began the school, business was poor because his students typically stayed for only a couple of months before leaving. He moved his school to Hoi Tan Street (海壇街) in Sham Shui Po and then to Lee Tat Street (利達街) in Yau Ma Tei. By that time some of his students were trained to a sufficiently high enough skill level that they were able to start their own schools.
Some of Yip Man's students and descendants compared their skills with other martial artists in combat. Their victory over other martial artists helped to bolster Yip Man's reputation as a teacher.
In 1967, Yip Man and some of his students established the Hong Kong Ving Tsun Athletic Association (香港詠春拳體育會).
Bruce Lee, Yip Man's most famous pupil, studied under him from 1954 to 1957. When Yip Man retired, many of his students were themselves teaching Wing Chun, including Wong Shun Leung, William Cheung, Lo Man Kam (Yip Man's nephew), Moy Yat and his two sons Yip Chun and Yip Ching.
In 1972, Yip Man suffered from throat cancer and subsequently died on December 2 of that year. As a fitting obituary for the man, within the three decades of his career in Hong Kong, he established a training system for Wing Chun and Wing Tsun that eventually spread across the world
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