Shoin’s father’s name was Sugi Yurinosuke Tsunemichi, a man of 62 koku income. He was devoted to agriculture, but even when he pounded rice, he kept a book on a shelf in front of him. He even read while working in the fields. (He had one younger sister Chiyo. His mother’s name was Kodama Taki.)

In 1834, he was pledged to his uncle Yoshida Daisuki Kenryo (a man of 57 koku), and was adopted in 1835, taking on the name Yoshida and Daijiro. Yoshida Daisuki who was of a slightly higher standing and was an ambitious man who studied the Chinese classics, wishing to establish his reputation as a scholar, but died when he was 29.

The Yoshida family was deeply loyal to the Emperor, and Confucianism and Strategy were diligently studied. The Yoshida’s belonged to the Yamagaryu – the school of Yamaga Soko. (Yamaga Soko had fallen into disfavor with the Bakufu and had been expelled from Edo in 1666 and sent to Ako, where he was exiled for ten years.) Shoin called him teacher – and was sympathetic to his ideas.

By order of the daimyo the teachers in military science, Watanabe Rokubei,Hayashi Shinjin, Tamaki Bunnonshin, and Ishizu Heishichi were made tutors and legal representatives for Shoin.

In 1838, Yoshida entered the Meirinkan, the clan school, as a pupil of Kagaku (Yamagaryu.). From this time until 1851 he lived partly with the Sugi family, partly with Tamaki Bunnoshin. Tamaki Bunnoshin, was another uncle who influenced him, and was known for later becoming the teacher of the famous general Nogi Maresuke (who stated “When you really desire to serve your country well then take the utmost care not to fall into mediocrity.”)

In 1841, Shoin learned horsemanship under the guidance of Hatana Genzaemon. In 1845 he joined the Shoka Sonjuku (of which Tamaki Bunnoschin was headmaster) and studied together with Matsumura Bunsho.

In 1845 Yoshida studied the Naganuma style of military science under Yamada Matasukie and in 1846, he lived temporarily with his tutor Hayashi Shinjin. At this time, he lost his books and clothing in an accidental fire.

On March 29th – he received a diploma of the Nagamuna style of military science and a book (the name and contents which were a clan secret ) called "heiyoroku" (short summary of military science) from Yamada. He also studied European Camp rules (formation) under Iida Inosuke (seiyo jimpo). Yoshida studied hembo (defense of the frontier) and composed Gaii Shoki (Short Notes on the Foreign Barbarians)

In 1847, at the age of 17, his fame had spread such that the daimyo came to visit his lessons and inspect the geographical maps made by Shoin and his disciples. (March and April).