Probably the best approach is just to say you want your character to feel more challenged.
'My character gets everything he wants a bit too easily. I'd like it if things were harder on him. In a lot of stories the characters really have to go through the ringer, I'd like a bit more of that.'
If you want actual challenge based play where real permanent failure is on the line, then you need the group and the GM to all be on board with it.
So is your dissatisfaction more:
A) In fiction the main characters tend to suffer horribly. 'Turns out the father you thought was dead is actually a commander in the enemy force, and he's just cut your hand off, and he wants you to join him.' 'You've been given a ring that corrodes your soul and you need to destroy it before the world is consumed by darkness. and you've just been stabbed by a ghost.' A majority of stories have far more failure than success or lots of set backs before success.
B) There is no strategic challenge. You as a player don't have to work to get what you want , you don't have to figure things out and strategize. Or to the extent you do it's easy.
If it's B (which it seems to be from what you've said) then I think you're probably out of luck if Kimberly doesn't understand that mode of play. The issue is that even if you manage to explain it, there is no guarantee she'll be interested or even capable. Where as A is probably a cake walk for an OC GM.
I tend to be pessimistic about mixed agendas though, so take what I'm saying with a grain of salt.
I was thinking/talking about (edit) B, but actually edit (A) is probably more relevant to the discussion. I think a lot of OC play tends strongly towards "Cosy Roleplay", I used Kim's game as an example. I think this is actually a pretty strong play mode compared to GMs who are nominally running a Trad game but are afraid to mess with the PCs. But I think probably most players, and certainly me, like a bit more Drama & even Sadness. It was something I like about another friend Jelly's GMing. She's definitely an OC style GM too, but she's very happy to do horrible things to my PC like taking away the testicles of my Tanuki PC (testicles are super important to Tanuki...) via a sex-swap, just when I was about to try to court a female Tanuki.
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