Translation guide
The ability to judge people and situations well and make good decisions, often in a practical or self-interested way.
The ability to understand situations and people quickly and accurately, and to use this understanding to make good decisions.
The ability to manipulate situations or people to one's advantage, often in a clever and sometimes unscrupulous way.
Cunning, slyness. A common word for shrewdness with a negative connotation, implying craftiness and a willingness to deceive.
彼はずる賢さで商売に成功した。
He succeeded in business through cunning.
The ability to make smart, often strategic decisions in professional or public affairs, with an eye for advantage.
There is no single Japanese word that perfectly matches all nuances of 'shrewdness'. The choice depends heavily on whether you want to emphasize positive insight, practical cleverness, or negative cunning. Using ずる賢さ when you mean 'astute' will sound insulting.
洞察力 is about deep understanding and perception, often intellectual. 抜け目なさ is about practical, worldly sharpness and not missing opportunities. The former is more positive, the latter can be neutral or slightly negative.
Insight, perceptiveness. Refers to the ability to see into the true nature of things. Often used for intellectual or analytical shrewdness.
彼は優れた洞察力で問題の本質を見抜いた。
With his keen insight, he saw through to the heart of the problem.
Foresight, prescience. The ability to anticipate future events or trends. Implies shrewdness in planning ahead.
彼女の先見の明にはいつも感心させられる。
I'm always impressed by her foresight.
Shrewdness in a practical, worldly sense. Implies being sharp, calculating, and not missing any opportunity. Can have a slightly negative nuance of being cunning.
彼の抜け目なさには誰もかなわない。
No one can match his shrewdness.
Keen eye, penetrating insight. A more literary or formal term for sharp perception and judgment.
彼の慧眼は多くの人を驚かせた。
His keen insight surprised many people.
Craftiness, wiliness. Similar to ずる賢さ but often implies a more malicious or wicked cleverness.
彼の悪賢さには警戒が必要だ。
You need to be on guard against his craftiness.
Cunning born of experience, slyness of an old fox. Used for someone who is shrewd in a worldly, experienced way.
彼の老獪さには敵わない。
I'm no match for his seasoned cunning.
Competence and shrewdness in handling affairs, especially in business. Often used in the phrase 敏腕家 (a shrewd operator).
彼は敏腕な経営者として知られている。
He is known as a shrewd manager.
A go-getter, a shrewd and capable person. Often used for someone who is effective and clever in business or negotiations.
彼女はなかなかのやり手だ。
She's quite a shrewd operator.