He spent a year in Canada and the US, working at various jobs, that included a salmon cannery in Alaska and house painting in Seattle.

Kawakami's first "self-drawn, self-carved, self-printed" (jiga-jikoku-jizuri: 自画自刻自摺) book made in the "creative-print" (sôsaku hanga; 創作版画) manner was published in 1927.

[2][1][3] In the early years, he developed a personal movable-type method for printing the texts by carving around 800 ideographs on individual small blocks of cherry wood (sakura: 桜 or 櫻), arranging the blocks within wood frames, and printing them with a traditional round rubbing pad (baren: 馬楝), just as he would do with his woodcut images.

His early woodcuts were made in the usual manner, "carving multiple blocks for the outlines and colors.

Besides of this, he frequently visited the workshop of Gôda Kiyoshi (合田清 1862-1938), who was skilled both in traditional woodcuts European techniques.

(Gôda's son, Koichi 弘一, was a classmate of Kawakami's at Aoyama Gakuin High School.

"[4][2] Kawakami was against Japanese militarism; during the Second World War he lost his job as the Ministry of Education banned the teaching of English language in schools.