Ikkyu Sojun’s life unfolded amid profound social and personal dislocation. Born as an illegitimate son to Emperor Go-Komatsu and a low-ranking woman, he carried the burden of marginalization and stigma from an early age. Separated from family and courtly life and sent to monasteries as a child, he grew up with a sense of rootlessness and insecurity that colored both his practice and his verse. This early fracture of identity and belonging became a quiet undercurrent in his later rejection of worldly status and institutional privilege.

Within the Zen establishment, Ikkyu encountered a different but equally piercing form of difficulty. Training in prominent Rinzai temples, he became deeply disillusioned by what he perceived as corruption, careerism, and empty ritual within institutional Zen. His outspoken critique of monastic hypocrisy and commercialized Buddhism led to persistent conflict with temple authorities and exclusion from positions of power. The tension between his recognition as an enlightened master and his refusal to conform to formal hierarchies created an ongoing struggle with religious institutions that never fully abated.

His inner life was marked by intense psychological and emotional trials. After the death of his mentor Kaso Sodon and other personal losses, he experienced profound despair, depression, and existential crisis, to the point of attempting suicide by drowning. These crises did not simply vanish with spiritual attainment; rather, they remained part of the terrain he had to navigate as he sought to reconcile spiritual aspiration with the raw force of human emotion and desire. Such struggles gave his teaching and poetry an unusually stark honesty, stripped of romantic idealization.

Materially and socially, Ikkyu chose a path that exposed him to hardship. Rejecting comfortable posts and secure patronage, he lived for long periods as a wandering monk in poverty, dependent on irregular support and hospitality. His open embrace of drinking houses, brothels, and the company of outcasts, as well as his late-life love relationship with the blind singer often called Shin or Mori, brought severe criticism and social ostracism from more conventional monks and lay supporters. Many saw his erotic and bawdy poems as scandalous, even degenerate, and his radical approach to Zen practice left him relatively isolated, with few contemporaries able to fully appreciate his stance.

The broader world around him was also in turmoil, adding another layer of challenge. He lived through a period of warfare and social upheaval that culminated in the devastation of major cultural and religious centers. When he later accepted the abbacy of Daitoku-ji, he faced the daunting task of sustaining and reviving authentic Zen practice in the midst of war, destruction, and moral decline. His repeated discomfort with institutional roles, and his threats to resign, reveal an ongoing struggle to maintain spiritual integrity while navigating the demands and compromises of public religious leadership.