Common Mistakes: “Challenging”

“I am a qualified candidate with a challenging personality.” This kind of phrasing appears on resumes and in cover letters from ESL writers fairly often. Yet, the word “challenging” does not express the intended meaning in this context — it actually suggests a negative impression of your character. Read on to learn all the details!

History & Definition

The roots of the word “challenge” go back to the ancient Latin word “calumnia”. “Calumnia” meant to accuse falsely or to slander someone. It was adopted into French as “chalenge”, and from there you can easily see how it came to be represented as “challenge” in English.

This old meaning, however, is somewhat different from the present one. First, “challenge” can function as a noun or a verb. As a noun, it refers to an obstacle or a problem that should be overcome. As a verb, it means to place yourself against something, whether a person or an idea.

For example, you can challenge someone to a fight, or you can challenge the belief that good things come to those who wait. In either case, you are setting yourself up as an opponent to the object.


Likewise, you can employ the gerund form of the verb “challenge” to describe things. You could describe a challenging test, which would mean it was difficult. You could also, as in the opening example, describe a challenging person.

However, saying someone has a “challenging personality” means (as with the challenging test) that they are difficult to work with. If someone describes a child as being “challenging”, it implies tactfully that he or she does not listen to instructions or follow rules. This is clearly not the image you want to promote of yourself in your resume, though!

Instead, use a word like “persistent”. Being “persistent” means you are someone who will never give up, no matter how big the challenge or how many times you fail on the way to success. Or, if you want to express the idea of being someone who goes beyond what is expected and challenges the things around them, you can use a word like “ambitious” or describe yourself as a “go-getter”. Both of these have positive connotations and present an image of someone who always pushes forward.

Remember: if you use the word “challenging” to describe something, substitute the word “difficult” into the sentence and see how it sounds. If it doesn’t sound good that way, you probably don’t want to use “challenging” in that context.

Let’s Practice!

Decide whether these example sentences are giving (a) positive or (b) negative descriptions. Check your answers at the end of the page!

  1. Climbing that mountain was an exhilarating challenge!
  2. My classmate is so challenging: he never works cooperatively.
  3. The pile of homework seemed an insurmountable challenge.
  4. I challenge you to a duel!
  5. What a challenging time of life that was, with all those mishaps.
  6. A challenge every now and then keeps your mind sharp.
  7. I would like to challenge the notion that being first is always best.
  8. Really important things are worth the challenge.
  9. I am someone who never shrinks from a challenge.
  10. I always challenge myself to think outside the box.

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  1. a: the challenge contributed to the person’s enjoyment
  2. b: the classmate seems to make the speaker’s life more difficult
  3. b: the person sounds depressed by too much work
  4. b: this usage is adversarial perhaps more than negative, but the speaker is against the person they are speaking to, so their interaction will not be positive
  5. b: this sounds like a time of struggle
  6. a: the challenge positively strengthens your critical thinking
  7. b: this is adversarial; the speaker has a negative view of the notion
  8. a: the “challenge” in this context is something negative you have to fight through to earn the positive things described, meaning those things are worth more than the negative challenges.
  9. a: the challenge is something problematic (negative), but the impression of the person in this sentence is positive since they are saying they are prepared for anything
  10. a: to “challenge yourself” means to push yourself (as though you were your own opponent in a competition) to do even better than your own previous achievement.

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