Born of a respectable family, the wealthy owner of a large farm and houses along the whole length of one street, he should have been a young nobleman leading a sheltered and protected life, never even allowing his hands to get wet with the warm water of spring. Yet, to the surprise of all, he showed a special liking for the art of fighting. So, at the age of thirteen, he received tuition in kung-fu from Chan Wah Shun, whose nickname was "Wah the money-changer", a favorite disciple of Grand Master Leung Jan of the town of Fatshan in the Kwangtung Province. As Wah the money-changer had to rent private premises for teaching his followers since he did not have a permanent site for his gymnasium, the father of Yip Man was kind enough to allow him to make use of the Ancestral Temple of the Yip clansmen. However, the high amount of the tuition fees imposed on his disciples, usually as much as three taels of silver a month, had resulted in a small number of students in his gymnasium. Yip Man, being the son of the owner of the premises, became closely associated with Wah. Attracted by Wah¹s kung-fu techniques, Yip Man eventually decided to follow him in the pursuit of the art of fighting. So one day, to Wah¹s surprise, Yip Man, bringing with him three taels of silver, requested that Wah admit him as a student. This aroused Wah¹s suspicion on how Yip Man had obtained the money. Upon inquiring into the matter from Yip¹s father, Wah found that Yip man had gotten the money by breaking his own savings pot to pay for tuition fees. Touched by Yip Man¹s eagerness and firm decision to learn kung-fu, Wah finally accepted him as a student, but did not teach him with much enthusiasm, as he regarded Yip Man as a young gentleman, too delicate for the fighting art. Nevertheless Yip man strove to learn much, using his own intelligence and the help of his elder kung-fu brothers (si-hings). This finally removed Wah¹s prejudice against him. He then began to adopt a serious attitude in teaching Yip Man the art of kung-fu. During Wah¹s thirty-six years of teaching, he had taught, in all, sixteen disciples, including his own son Chan Yu Min. Among these disciples of his, Yip Man was the youngest to have followed him and continued to do so until his death. Yip man was sixteen when his master Wah the money-changer died of a disease. In the same year he left Fatshan and went to Hong Kong to continue his education at St. Stephen¹s College.

During the years when Yip man was attending school, there was one incident, which he would never forget ­ an experience of a failure which turned out to be a blessing in disguise. It was a defeat in a fight that resulted in his obtaining the highest accomplishment in his kung-fu career. Being an active teenager, he was well involved with a group of youngsters from the school, who where all more or less the same age and were fond of quarreling with their European schoolmates. Having received tuition in the art of fighting, Yip man very often defeated his European opponents in fights, even though he was smaller in size. He admitted in his reminiscences some time later that he was too proud of himself in those days.

At this moment the elderly man smilingly told Yip man that he was allowed to attack any part of his body by any means, and that he himself would only discharge these attacks and would not render any counter attacks, nor would he hurt Yip man in any way. This only added fuel to Yip Man¹s fury. Nevertheless, Yip man managed to fight with care and calmness. He launched fierce attacks on the man, who discharged them with ease and leisure, and finally floored him, not just once, but repeatedly. Every time Yip man lay flat on the floor he rose again and rendered a new attack, only to find he had to leave in the end, defeated. It was later discovered that this elderly man was Mr. Leung Bik, the eldest son of Grand Master Leung Jan of Fatshan, the paternal teacher (si-fu) of Chan Wah Shun, the money-changer who had taught Yip Man. From then on Yip man followed Leung Bik for years and learned all the secrets of Wing Tsun Kuen. At the age of twenty-four, Yip man returned to his native town of Fatshan, having achieved competence in his art.

During the last few decades, Yip man was highly rated in the art of fighting by the people of Fatshan, but he never had the slightest thought of teaching his skills to anyone, always keeping the commandment of Wing Tsun that Œto spread it is in contrast to the wishes of the founder¹. He never intended to pass on his skills to anyone, not even his own son. This is why he never imagined that he would eventually become an instructor of his art.

In 1949, through the help of Lee Man, Yip Man was offered the post of kung-fu instructor of the Association of Restaurant Workers of Hong Kong. After a great deal of persuasion, he accepted. After two years of serving as the instructor Yip Man founded his own gymnasium in the district of Yaumatei in Kowloon and began to accept students other than restaurant workers. Later, when more and more students came to him he had to move his gymnasium to a larger site. Yip Man¹s fame and the practical value of Wing Tsun were especially admired by members of the police force, of which more and more attended his gym.

As his last effort towards the promotion of Wing Tsun Kuen before retiring from teaching he founded, in 1967, the Hong Kong Ving Tsun Athletic Association. In May 1970, when the classes in his gymnasium were firmly established, he decided to retire from teaching to enjoy a quiet life, having first passed all the affairs of his gymnasium and the teaching to his favorite disciple, Leung Ting.