Being well off is relative. One could be well off and downright miserable. One could be well off and have a drug problem, and smoke all his money away. Noted producer Scott Storch spent 30 mil in blow, and was buying Bentley's for Lil Kim, and they had to be repoed.
One could be well off and just happy, until their woman cheats on them or takes half. Or well off, but their family life sux eggs.
I wouldn't call myself well off, but I am Thankful for what I have and who I have around me. Thankful I have a job, friends, family to support me. In the eyes of many who don't have that, that is being well off.