My very first thought when reading this challenge was "great - I'll just marry a bunch of rich sims" then I noticed I couldn't add to household or manage worlds. I hadn't been playing the game for nearly enough time to know that clever loophole callycat used.
I had Monique O'lecta as as Creative Gloomy Perfectionist. I also made her first aspiration knowledge so that she had the Quick Learner trait too. First she became a tech guru and take all 3 vacation days so she she'd still get paid, then quit and rejoin and repeat. The rest of her days were spent endlessly painting although she also dabbed her hand and writing to get some daily royalties and even carpentry in the hopes it'd be profitable. But alas she was always either sad or confident (inspired was also dominated by these two) and I could get nowhere close to those top scorers.
And of course, congratuwelldone to ClayMask, just give us newbies a chance to get going though aha