Yi Jeong-am passed the licentiate examination in the fall of 1558 and passed the regular literary examination in 1561 as one of the third-tier passers. Starting his career with the Third Copyist of Diplomatic Documents Bureau, he served in various internal affairs and assistant section chiefs of several ministries. The following year, he served as an auditor of Jeolla Province, and then returned to the court to serve as assistant section chief of Ministry of Justice. In 1569, he moved to GyeonggiProvincial Government and became a drafter of the Chunchugwan. The following year, he was reappointed to the assistant section chief of Ministry of Justice to serve as a King’s Editor. Then, he was moved to Section Chief of Ministry of Military and dispatched to Gangwon Province as a secret royal inspector to inspect the disaster area. In 1571, he participated in the compilation of the Veritable Records of Myeongjong. In 1572, he was appointed to Second Assistant Master of Sungkyunkwan and observed the Chundangdae examination. In June of the same year, he became a prefect of Yonan and organized his military service. After serving as prefect of Yonan, Jangdan and Pyongsan, he was appointed to the magistrate of Yangju in 1579. As the magistrate of Yangju, he reconstructed Dobong Seowon and county schools. He also reformed the rice field plans and implemented Uniform Land-Tax Law in the entire area of Yangju. In 1583, he was selected as Jangnyeong, Saseong, and Jangakjeong when Yi I recruited scholars and founded Chansucheong. In 1587, he was designated as prefect of Dongnae to defend against the invasion of Japanese invaders. In 1591, he served as royal secretary and Councilor of Ministries of Public Works and Military affairs. In January 1592, he was the Councilor of Ministry of Personnel. When King Seonjo took refuge in Pyongan Province, he attempted to follow him. But he was late and he was already out of office and had no duty. He tried to defend Kaesong with his younger brother, Yi Jeong-hyeong, but failed due to the collapse of the Imjin Riverdefense line. In April, he entered the Hwanghae Province, became a Suppressor, recruited righteous army, and entered the Yonan Fortress with them. When Japanese Army led by Kuroda Nagamasa invaded, he defeated the Japanese enemy and firmly defended the castle. With the credit, he became an Governor of Hwanghae Province. In 1593, he served as Second Minister of Military, governor of Jeolla Province. However, after successfully defending the Yonan fortress, Yi proposed reinforcement negotiations to Seonjo, insisting on a quick end to the war, but was impeached and lost his official post. However, he was appointed to Deputy Magistrate of Jeonju in July of the same year In 1596, he became the governor of Chungcheong Province and contributed to the repression of the Yi Mong-hak’s Rebellion. However, he was dismissed under the charge of arbitrarily punishing prisoners, and in December of that year, he concurrently served as the Fourth Minister of the Office of Ministers-without-Portfolio and governor of Hwanghae Province. In 1597, when the Second Japanese Invasion broke out, he protected Suyang Fortress of Haeju as a Suppressor of Hwanghae Province. After the Japanese invasions of Korea, he resigned from his official post and spent his last years writing several works in Jeongjujeongsa Temple in Pungdeok. He died on September 10, 1600. After his death, various honors were bestowed upon him, including the title of Wolcheon Buwongun, an enrollment as the second rank of Seonmu Merit Subjects, and a posthumous offices, Jwauijeong.