> You'll probably work, but may not be able to replicate the same financial success you experienced previously, so it's hard to count on future income. If that

> You'll probably work, but may not be able to replicate the same financial success you experienced previously, so it's hard to count on future income. If that is the case, then you should focus on learning how to invest properly and on achieving, say, 10% annual returns yourself (i.e. without having to pay bank fees for subpar investment advice, which is what you usually get). Just because you made bank doesn't mean you have to get all conservative. Or at least, I wouldn't. One example: you could make calculated bets when there's "blood on the streets", e.g. wait (for years) until the market crashes, but when it does, leverage up that $14m to $50m and book a nice 20-30-40% gain. Or acquire an existing company using mostly debt (and a bit of equity), etc