I think it could be nice if they add a new type of job that has few tiers but is very much about taking big risks for potential big rewards. That could really spice up the game I think, and they would not have any way to advance other than through picking the right decisions during pop ups, but skills could come into play so you might only succeed if you are good enough in a relevant skill.
Daredevil for example could make a great return here, would also be an excuse to bring in some interesting daring activities.
The advancement would reflect their renown as a daredevil more, going from being an attention seeker to legendary daredevil.
Each pop up would be a different stunt, where you could make a few choices. Depending on what it is, your Sim could die from it, injure themselves, get sick or otherwise get some negative effects from it for a while. But succeeding would give them fame and cash. It could be the quickest way to fame mainly.
Some sort of criminal job could be perfect for this too, like maybe being a thief. Going from being a simple burglar or pick pocket to become a legendary thief or tomb raider. Would be the job that can make your sim rich the fastest, but can also cause them to have to pay fines, spend time in jail or stuff like that. Pop ups during their work would be about different actions to take during their heist, their abilities coming into play.
Stock broker could also work for this. Your sim could get filthy rich, but could also get into huge debts they have to repay. Could also work for gambler but I honestly think stock broker would be more interesting since it offers a legit job option in this category. Their pop ups would be more about who they advice their clients to invest money in and how much, skills could come less into play here and it could be more about luck and choosing either the safe way or the risky way that can make way more money.
