Although not trained for a political career in the traditional style, Sun was nevertheless ambitious and was troubled by the way China, which had clung to its traditional ways under the conservative Qing dynasty, suffered humiliation at the hands of more technologically advanced nations. Forsaking his medical practice in Guangzhou, he went north in 1894 to seek political fortunes. In a long letter to Li Hongzhang, governor-general of Zhili (Chihli, now Hebei) province, he set forth his ideas of how China could gain strength, but all he received from Li was a perfunctory endorsement of his scheme for an agricultural-sericultural association. With this scant reference, Sun went to Hawaii in October 1894 and founded an organization called the Revive China Society (Xingzhonghui), which became the forerunner of the secret revolutionary groups Sun later headed. As far as it can be determined, the membership was drawn entirely from natives of Guangdong and from lower social classes, such as clerks, peasants, and artisans.
In 1895 China suffered a serious defeat during the First Sino-Japanese War. There were two types of response. One group of intellectuals contended that the Manchu Qing government could restore its legitimacy by successfully modernizing. Stressing that overthrowing the Manchu would result in chaos and would lead to China being carved up by imperialists, intellectuals like Kang Youwei and Liang Qichao supported responding with initiatives like the Hundred Days' Reform. In another faction, Sun Yat-sen and others like Zou Rong wanted a revolution to replace the dynastic system with a modern nation-state in the form of a republic. The Hundred Day's reform turned out to be a failure by 1898
Taking advantage of China’s defeat in the Sino-Japanese War (1894–95) and the ensuing crisis, Sun went to Hong Kong in 1895 and plotted for an uprising in Guangzhou (Canton), the capital of his native province.
In the second year of the establishment of the Revive China society on 26 October 1895, the group planned and launched the First Guangzhou uprising against the Qing in Guangzhou. Yeung Kui-wan directed the uprising starting from Hong Kong. However, plans were leaked out and more than 70 members, including Lu Hao-tung, were captured by the Qing government. The uprising was a failure.When the scheme failed, he began a 16-year exile abroad.
Sun Yat-sen spent time living in Japan while in exile. He befriended and was financially aided by a democratic revolutionary named Miyazaki Toten. Most Japanese who actively worked with Sun were motivated by a pan-Asian fear of encroaching Western imperialism. While in Japan, Sun also met and befriended Mariano Ponce, then a diplomat of the First Philippine Republic. During the Philippine Revolution and the Philippine-American War, Sun helped Ponce procure weapons salvaged from the Imperial Japanese Army and ship the weapons to the Philippines. By helping the Philippine Republic, Sun hoped that the Filipinos would win their independence so that he could use the archipelago as a staging point of another revolution. However, as the war ended in July 1902, America emerged victorious from a bitter 3-year war against the Republic. Therefore, the Filipino dream of independence vanished with Sun's hopes of collaborating with the Philippines in his revolution in China
Second Uprising by Sun Yat-sen: On 22 October 1900 Sun launched the Huizhou uprising to attack Huizhou and provincial authorities in Guangdong. This came five years after the failed Guangzhou uprising. This time Sun appealed to the triads for help. This uprising was also a failure. Miyazaki who participated in the revolt with Sun wrote an account of this revolutionary effort under the title "33-year dream" in 1902.
Sun was in exile not only in Japan, but also in Europe, the United States, and Canada. He raised money for his revolutionary party and to support uprisings in China. In 1896 he was detained at the Chinese Legation in London, where the Chinese Imperial secret service planned to kill him. He was released after 12 days through the efforts of James Cantlie, The Times, and the Foreign Office, leaving Sun a hero in Britain.James Cantlie, Sun's former teacher at the Hong Kong College of Medicine for Chinese, maintained a lifelong friendship with Sun and would later write an early biography of Sun.