I don't know if it is the kind of "worst" you were thinking about, but in a previous helpdesk job I found a text file on a users desktop with a bunch of links. Asked the user what that was for, and they used it tonremember web sites. They were star struck when I showed them that bookmarks were a thing, and added their links as bookmarks for them to get started.
Here in Norway you are legally required to attend a few sessions with financial advisors(a protected title here, so they will actually be qualified), before you are able to recieve your winnings.
The rough thoughts I have had about being in such a situation is to allocate maybe 10%-20% as "fuck you money" to have fun with, and the rest to follow all their advice with