The failure mode in the long case that corresponds to "stock price suddenly skyrockets" in the short case is that the value of whatever currency you bought the stock with suddenly skyrockets relative to other assets.
Um, does this ever happen? Ever? It looks like an imaginary situation.
Besides, your description implies that you don't want to measure your wealth in money. What do you want to measure it in?
Value of USD (and many other currencies) against Zimbabwe Dollar skyrocketed pretty spectacularly in July 2008. I have a Z$10^12 note at home.
This is a rare, but absolutely possible, outcome.
This thread is for asking any questions that might seem obvious, tangential, silly or what-have-you. Don't be shy, everyone has holes in their knowledge, though the fewer and the smaller we can make them, the better.
Please be respectful of other people's admitting ignorance and don't mock them for it, as they're doing a noble thing.