During his third year studies at Akita Junior High School (秋田中学校, Akita chū gakkō), he moved to Tokyo to take up language studies at Mita English Language School (三田英語学校, Mita eigo gakkō), after which in 1883 he took the entrance exams for the Imperial College of Engineering (工部大学校, Kōbu Daigakkō) (now part of the University of Tokyo).

Shimoda gradually developed an inclination toward the theory of Evolution and the field of biology, and began to show disinterest in his college studies.

Together with the proceeds from this publication and his father's inheritance, he provided for his family, also raising capital for managing the architectural designs of Kinjyō School (Kinjō Gakkō) and private villas, he left for the United States.

In 1892 Shimoda submitted a personal entry in the architectural design competition for the California Pavilion at the 1893 World's Columbian Exposition, he lost to Brown, but moved to Chicago to take up a position as Construction Site Deputy Manager, improving his professional experience.

[4] It was during the Autumn of 1896 that Shimoda married an American citizen named Rose,[4] who was employed as Frank Lloyd Wright's secretary.

[4] When he received a visit from Katayama Tōkuma, the chief engineer to the Imperial House of Japan for the construction of Akasaka Palace, Shimoda introduced him to Daniel Burnham.

[3] At first he opened an architectural office in Tokyo, and worked to popularize low cost steel frame construction methods, but met with opposition from Kingo Tatsuno, and in 1901 he moved to Yokohama to establish Shimoda & Co. Construction Company (下田築造合資会社, Shimoda Chikuzō Gōshi Kaisha), which specialized in architectural and building services exclusive to the foreign expatriate community.

[9] During this period, Shimoda was also involved in a dispute over claims about his design proposal for the Imperial Hotel, Tokyo, which was later formally awarded as a commission to Frank Lloyd Wright.