Negative connotation:
* Difficult, frustrating, or overwhelming: "The project was incredibly challenging and made me feel stressed."
* Something that tests our limits or makes us doubt our abilities: "The job is very challenging, and I'm not sure if I'm up to it."
Positive connotation:
* Stimulating, exciting, or rewarding: "The hike was challenging, but the view from the top was worth it."
* Something that encourages growth and development: "The new training program is challenging, but it's helping us improve our skills."
Ultimately, the connotation of "challenging" depends on the speaker's perspective and the specific context in which the word is used.