I have a couple of family members who fall in the category you're talking about here, and here's what I've seen from them: 1) when you have a lot of assets, you

I have a couple of family members who fall in the category you're talking about here, and here's what I've seen from them: 1) when you have a lot of assets, you still need to keep your eyes on them and have a system for monitoring and managing them quickly. But you never really get to the point of "set and forget". 2) You might be at a point where your income is essentially guaranteed for the rest of your life, and very adequate. But you probably only have a few (if any) friends in the same financial situation. That means that you might be able to stop working and just travel or do things you find interesting, but you will probably find that those things are only interesting for a short time when you are doing them alone. So you start a little side project for fun and for something to do, and it is successful and starts to grow quickly and now you are working again, because permanent vacation is honestly pretty boring.