The Words of the Samurai – Episode 17

The Bold Strategist: Date Masamune

In the turbulent Sengoku era, Date Masamune rose as one of the boldest and most iconic leaders of his time. Known as the “One-Eyed Dragon,” he stood out not only for his military ambition but for his willingness to act decisively. This episode explores a quote that captures his fearless, results-driven mindset — a stark contrast to the overcautious attitudes common in warfare.

Strike before hesitation sets in: The samurai strategy of decisive action

During Japan’s Sengoku era, Date Masamune — the ambitious warlord from the Tōhoku region — earned several nicknames. The most famous is “Dokuganryū” (the One-Eyed Dragon), but another widely known title was “the man of decisive action”.

Kadan means to take action boldly and without hesitation. Masamune was known to say:

“When people try to do something, they worry: ‘What if this happens?’ or ‘What if that’s dangerous?’ But what’s the point of all that? Things may seem determined, but they really aren’t. Instead of stressing over an uncertain future, it’s better to focus on what’s right in front of you. In war, surprise attacks often lead to victory. Taking action without delay is the mark of a truly brave commander.”

Masamune defied many conventions of his era — like sending his retainers all the way to Rome. That too showed his bold spirit.

He lived well into the era of the third shōgun, Tokugawa Iemitsu. His farewell poem says a lot about how he lived:

“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 approach, act fast, act boldly, still resonates as a model for modern leadership. Whether through international diplomacy or his poetic farewell, he lived with purpose and consistency. His words remain a powerful lesson: in moments of uncertainty, action and resolve matter more than fear and hesitation.