A challenge is always healthy, it keeps you in shape and I think for something to be a challenge you need to step out of your own comfort zone and it's not always that easy and some challenges can end in failure, but it's always good to push yourself. I think it's too easy to be comfortable in your own writing style and it was something I was pressed to do last year. Typically my writing tends to end on a depressing note and things tend to be on the low note quite frequently, my challenge was to write on a high note, have something happy. What happened? I wrote about a father trying to spark a relationship with his son after a history of abuse, I guess the 'high note' is that there's a relationship on the way to repair. Then further attempts were just too facetious and it ended on working on a piece of fluff, but the twist was that the lover was severely ill and I was trying to play on the power of love (sticking with someone, it ends on joy and happiness) it was actually pretty crap, but I guess I feel for a character to appreciate the 'good' they got then they've got to work for it as work makes it all the sweeter, but perhaps I should avoid using extremes.
But look at your own writing style, look for what's common and see what you can do to change that - if you mainly writing in the third person, write in the first person and if you primarily write in one genre, write in another, perhaps one you've never even read, you never know, you might find you like it.
An interesting challenge is called 'Write Or Die', set yourself a target for a number of words and time to write them in. 'Write of Die' will punish you for not writing, you can change different settings to suit you, but my favourite punishment is 'Kamikaze Mode', where if you stop writing after a period of time it will start deleting words so it keeps you on your feet and have you thinking creatively. Combine this with NaNoWriMo, you're going to get good progress on writing,
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