1.

Here are a couple great words to describe a clever person: Astute and shrewd. Although these words both mean clever, they can be used quite differently.

Shrewd is derived from the word shrew, which means "wicked man." Shrewd can be used to describe people and/or business practices that are both smart and underhanded. Shrewd is similar to astute, since both words are used to describe sound judgment and practical intelligence, but, in contrast to the word astute, the word shrewd can carry a negative connotation, because it's usually used to describe someone who is sharp and intelligent, but potentially underhanded at the same time.

For example: The shrewd attorney always finds a way to win a case, while an astute investor finds a way to make money through research and intelligence.

2.

Since we just discussed cleverness and intelligence, let’s look at several great words to describe someone who is wise and intelligent and makes intelligent choices in life: discerning, judicious, sagacious, astute, and assiduous.

Sagacious is a more formal and sophisticated way of saying "wise." You may have heard the related adjective sage. Sage is also a more sophisticated way of saying wise. You have probably heard the phrase “sage advice,” meaning wise advice. Since sagacious is derived from a word that means "prophetic," or able to predict the future, use sagacious to describe someone who is wise and experienced enough to predict the future or anticipate problems and plan accordingly. Therefore, someone who is sagacious is insightful and observant. Someone who is discerning also shows insight and good judgment, specifically when making decisions. A discerning person is sensitive to the differences between two or more choices and is able to use good judgment in making choices. You could also describe this person as judicious--having good judgment. An astute person also has intelligence and makes good decisions, usually based on logic and pragmatism. One place you’ll often hear the word astute is in the context of investing decisions

An astute investor makes investment decisions based on sound research, not “hot stock tips.” An astute investor is usually assiduous, meaning he or she performs extensive research before making a decision. A person who is generally sagacious would likely also be an astute investor. This person would be able to make discerning choices (that is, the person would be able to discern) between good investments and bad ones based on experience and wisdom.

To recap: If you wanted to comment on someone who makes smart decisions based on careful and assiduous research, you would say this person is -- astute. If you wanted to comment on someone who makes smart decisions based on experience and wisdom you would say this person is -- sagacious. If you wanted to comment on someone who is able to choose the best decision between different options you would say this person is -- discerning. Finally, if someone uses good judgment to make decisions, you would say this person is -- judicious.

3.

In our last lesson, we took a closer look at the word judicious. Since judicious refers to having good judgement and making sound decisions, we can probably assume that a judicious person would be a careful person. Now, what words can you think of that mean “careful,” but are a little more sophisticated and specific to context?

How about circumspect, prudent and wary… Circumspect means “aware of potential consequences.” Someone who is generally circumspect isn’t likely to take risks. Circumspect comes from a Latin origin meaning “to look around.” If you are circumspect, you’re careful to look around you, in a figurative sense, and be aware of what’s going on and what could potentially happen. A circumspect person doesn’t assume or take things for granted. Likewise, a person who is prudent isn’t likely to act on impulse, but is careful, watchful, and shows good judgment. A prudent person knows when to speak up and when to keep silent. Prudent refers more to specific actions, while circumspect refers more to a person’s general character.

For example, “Being circumspect, he was prudent to have the house thoroughly inspected before purchasing it.” Someone who is wary is highly circumspect and always prudent. A wary person is likely to be mistrustful and guarded in his or her actions. If you were wary, you might say something like: “I was wary of sharing the details of my plans with him because I wasn’t sure I could trust him.”

To recap: If someone is cautious and slightly mistrusting, you would say he or she is -- circumspect. If someone is cautious and does research before making a decision, he or she is considered -- prudent. Finally, a person who is cautious and generally mistrusting of a situation, is -- wary.