How to make rags to riches more fun?

I attempted rags to riches several times before but every time I drop it cus its too boring. I know ways to earn s shit ton of money pretty quickly without a job. Once you get your hands on a dragon fruit the challenge is basically over. So what are somew fun ways to earn money? Where it's enough bit not too much too soon. Getting money from only selling collectibles sounds exhausting for example. Should I just committ to one of the creative skills like painting or writing?