By that time I stop enjoying doing whatever the thing is. Not fun anymore.
People will sincerely praise me and it will feel empty because I know there are millions of better painters, my laptimes are a full second off the ultimate pace, my guitar skills only good enough for playing alone in my office, my leisure programming projects all pointless and abandoned.
I envy two kinds of people: those that have found some thing they are very good at and keep enjoying it forever, but also those that can enjoy something for years even if they are realistically mediocre at it and never improve.
And the money making part is also true for me. I took up miniature painting and quite soon was at the level where people will pay you decent money to paint their miniatures for them. I started getting offers and accepted one, not for the money, probably just out of pride. It was complete hell, I hated the result and every minute I spent painting it. The client was happy, me, I guess I learned my lesson: never again.