The Man of Decisive Action: Date Masamune

Date Masamune, the famed “One-Eyed Dragon” of the Sengoku period, was as much a master strategist as he was a bold and unconventional leader. In this episode, we explore one of his most pragmatic declarations — one that defies hesitation and champions immediate action. At a time when fear of the unknown could paralyse even seasoned generals, Masamune stood apart for his decisiveness.

Seize the moment before doubt arises: A samurai’s tactical mindset

During the Sengoku period, Date Masamune — the warlord who sought to unify Japan from the Tōhoku region — was known by many names. The most famous is “Dokuganryū” (the One-Eyed Dragon), but another well-known epithet is “the man of decisive action”.

Kadan refers to the act of boldly carrying something out without hesitation. Masamune was often quoted as saying:

“When people take on something, they tend to worry — ‘What if this happens?’, ‘What if that’s dangerous?’ — but what’s the point? Things may seem set, but they rarely are. Rather than worry about an uncertain future, it’s better to act on what lies directly in front of you. In battle, victory is often achieved through surprise. Acting without delay is the true honour of a brave commander.”

Masamune broke many taboos of his time — notably sending his retainers to Rome — a gesture that also reflects his bold nature.

He lived into the era of the third shōgun, Tokugawa Iemitsu. The way he lived is well reflected in his death poem:

“The cloudless moon of my heart is my guide, casting light on the darkness of this sorrowful world as I set out on my journey.”

Masamune’s belief in seizing the moment and acting without delay reflects a deeply rational and forward-thinking mindset. His bold moves, including sending emissaries to Europe, and his death poem show a man who truly lived by his principles. His legacy endures as a reminder that clarity and courage are the greatest tools of command.